Legal Tech

Episode 17: Stephen Kane on Online Dispute Resolution

This time we talk ODR, short for online dispute resolution, with Stephen Kane, the founder of Fairclaims a platform that helps people resolve legal claims online.

As Stephen explains, ODR has been around since the 1990s, but really took off when companies like Ebay and Amazon started to use it to resolve customer complaints and disputes.

ODR can look a lot like a terrestrial arbitration or mediation–documents and evidence are exchanged online and an arbitrator or mediator tries to settle the dispute. But, disputes can also be resolved online without any human intervention at all.

If you want to contact Stephen, you can find him on Twitter or contact Fairclaims at


Legal Tech Founder Segment: Tucker Cottingham of Lawyaw

This episode is a two-for-one in the legal tech founder department because for our legal tech founder segment, we talk to Tucker Cottingham, the CEO and co-founder of Lawyaw, a document automation and assembly tool for lawyers. Lawyaw helps lawyers cut down on document assembly time by auto-filling court forms and turning Microsoft Word-based legal documents into online templates.


Things We Talk About in This Episode:

Los Angeles County ODR Program

European Commission Online Dispute Resolution

Judicial Council Forms


Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI


Episode Transcript

Chad Main:          That’s Stephen Kane. He’s the founder of a company called FairClaims. In today’s show we talk to him about ODR or Online Dispute Resolution. Instead of going to court to resolve a legal problem, ODR permits parties to resolve legal disputes online.

In our legal founder’s segment, we talked to Tucker Cottingham. He’s the co-founder and CEO of Lawyaw, the document automation and assembly tool. I’m Chad Main and this is Technically Legal, a podcast about the intersection of technology and the practice of law. In each episode we talk to a legal innovator about what they’ve been up to and hopefully get a couple of real world tips from them about implementing technology into legal practice.

Not only is Stephen the founder of FairClaims, he’s a lawyer. FairClaims is an ODR platform that permits parties to resolve legal disputes online rather than via more traditional means like heading to court. But, what is ODR exactly? 

Stephen Kane:       Use technology to more efficiently resolve disputes. Thereby making it quicker and less expensive to all stakeholders to get to resolution.


History of ODR

Chad Main:          At a very general level, there are a few main types of online dispute resolution. Some aren’t hugely different than the dispute resolution solutions we’re used to. For instance, as we will hear in this episode, both arbitrations and mediations can be conducted online through platforms like FairClaims. In those situations, rather than relying on court fines and hard copy memos, evidence and arguments are submitted electronically. However, there are also purely tech-based solutions where disputes are resolved solely by algorithm with little to no human decision-making input.

While ODR is somewhat newish, it has been around for a little bit. At least since the 1990s. When the general public really started using the internet and searching the world wide web, it was inevitable that disputes would arise. Some of the very first ODR programs were launched at colleges and universities and focused on the study of ODR, but also attempted to resolve disputes between students or domestic-related disputes. When commerce on the web took off, sites like Ebay and amazon embraced ODR for the resolution of customer complaints and disputes. That’s when online dispute resolution really took hold.

Stephen Kane:       People were talking about it 30, 40 years ago because I remember, I went to law school, I was a 2006 grad, and I read articles in law school and that’s what got me thinking about it when I was talking to my own clients about small disputes. I read articles then about people who were talking about it in the ’80s. The moment that there was the personal computer, the idea of connecting computers. Certainly the moment the internet was around, people were talking about it. It’s been decades in the making. Different companies have succeeded in different ways. It’s been attempted at least a dozen times, probably more. As far as the history goes, it’s been an idea for decades and then, I would say the first company that people would agree developed ODR would probably be Ebay, actually.

Consumers don’t necessarily think of the Ebay forums as dispute resolution but it’s very much dispute resolution. Same thing with Amazon. Amazon and Ebay were two of the first companies to really execute on dispute resolution. When you go to Amazon, you miss a package, it’s a few clicks.

Chad Main:          Expand on how Ebay and Amazon, what kinds of disputes they’re resolving and how it works because I think some people, they wouldn’t think of that as online dispute resolution.

Stephen Kane:       It totally is and yeah, because some people think, “Okay. Online dispute resolution is an alternative to litigation.” That’s totally true but, online dispute resolution also gets in front of litigation. In our world at FairClaims, we think information is dispute resolution. If you and I are debating who’s in a movie like, was Will Smith in that movie? We google it now and we resolve the dispute. When I was a teenager, we would debate it, there was no resolution. We would just debate it. We would’ve had to go to the library or happen to see it on the news because I was around when AOL first got started. That’s a form of dispute resolution and I agree that it’s not necessarily in people’s mind share, and I don’t think ODR’s in people’s mind share in general per se. But yes, with Amazon and Ebay … with Ebay, let’s say your package gets there. You buy something from a seller and it arrives damaged. If there weren’t tools on Ebay to resolve disputes, what would you do? You might hire and attorney, you might sue them. It depends on the value of the package.

But if it were a hundred-dollar package, you’d probably have to just walk away. But one of the genius things about Ebay and Amazon is you don’t have to walk away. They set it up so that you can easily resolve things and get ahead of litigation so that I would imagine, and I’m not a lawyer there, that they’ve had less litigation over the years versus other companies.

Chad Main:          For the most part, there’s no human involved in the resolution of most of those claims, correct?

Stephen Kane:       Correct. In terms of volume, there’s no human involved. They try to resolve it digitally first just with some exchange of information. However, Ebay built a huge panel of mediators way early on. I don’t know the exact year, but they had volunteer mediators so that there would be digital solutions and then, you could get a human mediator. So few people go through dispute resolution because disputes only come up half a percent of every transaction or so. Most people don’t experience it. People experience disputes but they haven’t necessarily experienced a dispute on Ebay. I think more salient, they don’t necessarily think about it as dispute resolution. That’s beautiful because if you’re not thinking about it as dispute resolution, you’re just thinking I need to solve this problem, and I think that’s what law should be.


Why Stephen Started FairClaims

Chad Main:          Like many of the people we talked to on this podcast, Stephen was a lawyer in private practice before he launched FairClaims. In his practice, he saw a pain point in the legal industry that was not adequately being addressed. But it was a probably that tech might be able to help. Specifically, the resolution of legal disputes involving parties that might not be able to afford lawyers or disputes that maybe didn’t even really need the involvement of lawyers.

Stephen Kane:       I’m sitting here at a recording studio in the arts district in downtown LA. I grew up a couple miles from here. I grew up mostly in Monterrey Park and grew up also in downtown LA. The reason that experience is relevant is I grew up not rich. I can’t say I grew up poor because I had everything I needed. But there was a six-month period for example where my mother who worked for the city government most of her career was out of work. That was very anxiety producing. Most of my family still lives like most people where they’re living paycheck to paycheck. I’m still living paycheck to paycheck. I’m totally fine and compared to most people, I’m super wealthy or rich or whatever, but I think that because of all of that and because I’ve struggled still in my adult life and I’m about to turn 40 in two weeks. 

Because of that, I still empathize with people who go through struggle who don’t have access to an attorney like 90% do not who have no idea what to do when they get into some sort of legal dispute or situation. As most of my family has no idea what to do when they’re in some sort of … not even necessarily litigation. I’m not talking about that. I see it all the time. Since I started FairClaims, and I’ve been working on it for four and a half years, it’s amazing how many phone calls I still get about disputes. People, they don’t know what to do about it and how simple it is for me with my legal background to give them two bits of information or something where they can do something about it. That’s the motivation for FairClaims and I think one of the reasons for our success is that I’ve recruited a team of people who are in a similar boat.

Not necessarily that they’re all struggling. Some of them have a good amount of money. Some of them have spouses who make money, but some of them don’t and I think that means that we’re all empathetic of what our end users go through.

Chad Main:          What was it within your practice or about your practice that gave you the aha moment and says, “You know what? There’s gotta be a better way to resolve disputes?”

Stephen Kane:       I kept getting calls from people with small claim disputes they weren’t sure what to do about. Usually it was the typical story and I would get about four or five calls a month was, “Somebody owes me $2500.” Or, “I had a work-for-hire or a contract for $3000.” Or, “A home-improvement project for a couple thousand.” Or a landlord tenant issue of $1500 security deposit and they didn’t know what to do about it. They called me because that’s what people do if they can. They call a lawyer. I offer free consultations. I think it was an effective way to get clients. I would have to explain to them and it was heartbreaking really, that, “Hey, I actually can’t help you because I’m gonna cost more than the claim is worth.” Then they would say, “Well, but then what do I do?” I’d say, “Well, you could go to small claims court.” 

Small claims court of course is a nice option. The courts are very good people with difficult roles who have a lot of volume coming their way and I would explain to them how that process worked and that they would have to look the court up, file paperwork, that I could only help them really just because I only did this part-time. I had to make money of course for my time if they paid me and that wouldn’t be worth it so that they had to go get paperwork, go submit it, serve the other side, go appear. They get their court date, it’s two to three months out. Go appear in person, make their own arguments. I could just tell they were … a lot of them were intimidated by the process. It was tough that there was that timeline when $2000 would make all the difference for their budget, whatever that was. The fact that they had to stand in from of a crowded packed courtroom and make an argument and et cetera, et cetera.

The point is that it’s a tricky situation for people when they have to navigate things on their own and just got me thinking, “Isn’t there’s something out there?” Because, at the time it was 2014. “Isn’t something out there that can help people?” I went searching, and I personally did not find something that I thought made sense for them. I don’t know what happened. Something clicked, I couldn’t stop thinking about it. I got obsessed and so I started just sending an hour a day thinking about it, working on it. I remember taking a trip to Utah where I thought, “I can make money with legal work. This is interesting to me,” and I set out to start I don’t know what. A little website, a small business. I never thought it would turn into a thing.


FairClaims’ Business Model

Chad Main:          Stephen launched FairClaims in 2014 as he phased out his law practice. For now, FairClaims mainly handles disputes under $25000 and many are related to insurance claims. However, the company continues to grow.

Stephen Kane:       We want to help people resolve any disputes under $25000 period, and we’re set up to do that now. We have a series of escalations. Our philosophy is resolve early, resolve often and avoid headache. If you go to your site, it’s be heard, resolve, move on. That’s how we think about it that in a perfect world, we all resolve disputes very quickly so there’s less stress and anxiety and worry and so that everybody gets to resolution quicker which means you can reduce your liability and get paid out and et cetera. But we can handle any monetary claim under $25000. What we do is we have a full stack that starts with information and resources. We’re giving you information about your dispute. That’s only built out for insurance claims right now.

We started working with marketplaces first. HomeAdvisor and Turo and companies like that where we mainly use arbitration and mediation. But, insurance is a great example of where we have the entire A to Z solution. A claimant comes in, first they look at literally some information about insurance claims. Some resources. It’s certainly not legal advice. It’s not specific.

Chad Main:          When you say information, you mean how the claim’s gonna proceed, what’s expected of them, what to expect in general?

Stephen Kane:       That’s basically right. Because, I think we did a lot of customer development. I’m sure a lot of us know people who have been in an auto accident. When you’re in an auto accident, no one’s sure what to do. I didn’t know anything about what to do 14 months ago. The first step is, “Hey, here’s some basics on what goes on with an auto accident claim.” That’s the first step and then, “Here’s some resources and you can go research some stuff.” Then they can go google things and we say, “Don’t take our word for it.” We are partnered with different people like the Better Business Bureau and that helps us. We have articles on our site. Good social proof, but we say basically they can look it up themselves.

That’s the first step, info and resources. Then there’s an intake module where they can kinda … we have some videos about more about how the process works. They can add information about their claim. They can add different aspects. Medical bills, property damage. Is there anything else that we need to solve for to resolve things here? Are you in pain still? When are you gonna recover? That sort of thing and it automatically walks them through a TurboTax type tool. But what we do, and this is where my co-founder John is a total product genius. Total genius. We empower them to think for themselves about what they think is fair. What that does is a couple things. One, it makes them think about it and then, it helps them consider the trade-offs of, if I want more money, is it gonna take longer? Can I cover all my bills? But more important than that, it empowers them.

I bought a hat. I went to Yale Law School a couple weeks ago to visit. I just happened to be driving from Hartford to Manhattan. I had never been on campus. It’s a beautiful campus. It looks like a bunch of castles. I bought a Yale Law School hat and our thing is we are all Yale attorneys or we could be. Because, when I do TurboTax I’m a pretty damn good accountant. That’s the idea is hey, this stuff’s actually not rocket science. A lot of it. Now, some of it is. Some of it is. If it’s a complex claim, if it’s over $25000, if it’s more than just soft tissue damage, FairClaims is not for them. Again, we don’t give legal advice but it’s more like if you give people some info and resources, if you let them walk through the elements of an insurance claim, which actually doesn’t have to be complicated, I think insurance companies have very sophisticated ways of doing things for good reasons. But, from the claimant’s perspective, it can be very simple.

What we found out in talking to them is hey, I just want a fair payment quickly. What they want is something in between. Perhaps a Google search and talking to their cousin and hiring an attorney. Now, if they go through our tool, they still have the option of hiring an attorney, and that’s fine. Some people will always want to hire an attorney but some people want a different option like a TurboTax type option. They go through and they see that, and we’re very transparent. It says, “Look, what this comes down to is who’s at fault and how much. There’s some other stuff involved, but it’s really about property damage, medical bills and then if you’re in pain there could be perhaps a pain and suffering component. We introduce some information on how they could think about guidelines. They decide for themselves what they think is fair.

I was in an auto accident two years ago. My self-esteem was low after that accident. When you’re just taken off guard and you slam into a wall, you feel a little down. We’re trying to build people back up again in this way that shows them, hey, you can do this. You’re gonna be okay. We can facilitate something to get you somewhere quickly. That’s the next step and then they go and immediately they can then decide if they want to submit it to the claims adjuster at the insurance company or not. People can literally go into our tool, get information and then go hire an attorney. They can go on our tool, get information and [inaudible 00:15:34] the attorney. They can go on our tool for fun. It’s free for consumers. But if they would like to then submit that information to the insurance company they can do that. Then, right away they’re taken into a negotiation platform where they can make offers and counter offers back and forth if they’d like. Then, they go into a mediation platform to discuss the matter with the insurance company.

Chad Main:          If the negotiation fails, then they go to mediation.

Stephen Kane:       That’s correct.

Chad Main:          I assume the negotiation’s with the claims adjuster as maybe had they hired an attorney it would be?

Stephen Kane:       Yeah, correct. Look, claimants can do this. Whether or not they have an attorney, they can do this alongside thinking about hiring an attorney. It’s a perfectly valid option either way and again, many cases where they absolutely should get an attorney but, hopefully maybe things settle in the negotiation platform and both sides are happy. If not, then they can call in a third-party neutral mediator who’s totally separate from FairClaims. It’s a 1099 and that person has insurance experience in their state, and they work it out from there.

Chad Main:          Is the mediation also facilitated on the FairClaims site?

Stephen Kane:       Yes.

Chad Main:          Okay. What happens if mediation falls through?

Stephen Kane:       In that particular flow for auto accidents, then unfortunately that means they didn’t get their resolution. We don’t recommend arbitration for most insurance claims. We think arbitration is a separate solution for separate types of problems. We do think there’s a place for arbitration with some insurance claims, like when it’s just property damage and they’re at an impasse. We have done that for other companies. We do it voluntary, not mandatory. Then, there’s a digital solution there where within two to three weeks, the arbitrator makes a decision. There’s a video hearing included.

Chad Main:          We just talked about insurance claims relating to auto accidents. Does FairClaims offer arbitration for other types of disputes?

Stephen Kane:       Absolutely. We can handle anything and with our marketplace customers, with the sharing economy customers we work with, the main solution’s arbitration. Some of them use … we call it fairchat. Our mediation tool which is like … it’s a chat tool, you can upload evidence. There’s some automated messages from FairClaims to help drive the conversation. There’s some deadlines. You can do a video call or a phone call for mediation as well. But absolutely, we can handle any arbitration under $25000.

Chad Main:          It’s basically a tool open to anybody. If you and I get into a dispute over I don’t know, we decide to start a business and it falls through. If we decide, you and I, to use FairClaims to resolve that dispute, it is open to us, right?

Stephen Kane:       Correct.

Chad Main:          It would be submitted to an arbitrator or you could do a mediation or arbitration?

Stephen Kane:       Correct. We even put the mediation tool within the arbitration platform and about 15% of our cases … I shouldn’t say cases, our arbitration matters settle with that mediation tool.


Legal Founder Segment: Tucker Cottingham of Lawyaw

Chad Main:          We’re gonna step away from our talk with Stephen for just a few minutes because now it’s time for our legal founder’s segment. Today we’re talking to Tucker Cottingham. He’s the CEO and co-founder of Lawyaw, and that’s spelled L-A-W-Y-A-W. It’s a document automation and assembly tool. Tucker, thanks for being here today. I appreciate your time. Tell us a little be about Lawyaw.

Tucker C:           Yeah, absolutely. Thanks for having me. Lawyaw is a cloud-based platform and with Lawyaw, attorneys can upload their word-based legal documents. Then, we use software to turn them into templates that can be easily and quickly filled out online. Unlike other programs that use pre-can language, Lawyaw creates templates out of the documents attorneys already have created. They use their own well-crafted words, their own documents and turn those documents into templates.

Chad Main:          It’s a cloud-based app, correct?

Tucker C:           It’s 100% cloud-based. You can use it from a Mac or PC or iPad on the go, exactly.

Chad Main:          What was the motivation or inspiration to create the app?

Tucker C:           I’m an attorney and I worked at a small law firm in San Francisco and spent a lot of time dealing with a lot of similar documents. We would use the same documents over and over again but we’d have to change bits and pieces of them and customize them to clients but, a lot of the language was gonna be the same across different projects. What we found is that it’s really unfair that attorneys who want to streamline their document drafting have to choose between really elementary tools that have a lot of limited flexibility, or these more complex programs that are really expensive and hard to use. When faced between these two options of something really simple and limited or something really complex and expensive, most firms just don’t end up doing anything. We decided to help attorneys achieve their goals by creating software that’s really powerful and also allows them to realize their benefits immediately. Occupying that middle space between the existing options right now.

Chad Main:          Let’s talk about that for a minute. The benefits. Tell us about some of the features that Lawyaw has.

Tucker C:           If you have a document on your computer, you can open up Microsoft Word. We have a add-in that allows you to easily turn that document into a dynamic template. What I mean by that is it’s not just fill in the blank. You can save alternative clauses, you can have multiple choices for different sections of the document, you can save formatted text, you can give yourself hints. You can turn your documents into these flexible templates and then, you sync it with Lawyaw and you log into Lawyaw and you can fill out the journey that you’ve created and generate that document. You can have multiple users on your account so you can manage your templates across your firm very easily. We also have a federally compliant e-sign tool so that when you actually generate the document, you can either download it back into Microsoft Word and do additional custom edits, or you can go directly to e-sign and send it out for signature. You can also upload outside documents back into Lawyaw and send them out for signature.

Chad Main:          Not only custom made Word Documents, the app also lets you fill in judicial council forms if you’re a California attorney, right?

Tucker C:           Yeah. We have about 6000 standard court forms and California’s a great example. California is super heavy on pre-printed court forms. There’s 58 counties and they all have their own forms and then there’s the judicial council that has about 2000 forms. We have a library of standard court forms. We also have all the immigration forms in addition to the ability to turn your own documents into these flexible templates.

Chad Main:          You use Word-based documents to load into it for templates, so I assume that it works with a Google Doc too if you save it in the right format?

Tucker C:           If you export your Google Doc into Word then it will definitely work. What we’ve found is the vast majority of attorneys are still using Microsoft Word and that’s where they have their existing documents. Rather than having somebody rebuild a document from scratch, you can just open a document that you already have, quickly turn it into a template and sync it with Lawyaw.

Chad Main:          Who is the target audience for Lawyaw? Is it small firms? Big firms? Middle firms? Any type of law department? Any type of lawyer?

Tucker C:           Yeah. Really we’re targeting small firms from two people all the way up to 100 attorneys. That’s the segment of the market that really doesn’t have great options right now. Those are the attorneys that are really based between a really inflexible option that’s really simple or a really complex expensive option. We’re targeting both litigation attorneys and transactional attorneys and in small firms.

Chad Main:          That brings up a point too is it really doesn’t matter what type of law you’re practicing because you probably have the same types of documents you’re doing over and over and over for your clients. 

Tucker C:           Exactly. What we’ve found is that each law firm is unique and has their own documents, but it’s a similar set of problems that they’re all facing which is that they have templates that they use, or they go to a previous client project and they make changes in that previous document. Those are all essentially templates. Attorneys that have been doing this for a long time, they know their documents really well. They know the process really well and what we’re helping them to do is to streamline that process using our cloud-based platform.

Chad Main:          To that point when you demoed it for me before we hopped on here, you showed me pleading template and a fee agreement template. You got a contract and a pleading. There’s two different types of documents. It’s really pretty amendable to any kind of document. Any kind of legal document that has variables and is consistently used, right?

Tucker C:           Yeah, exactly. Some of the commonly used documents are gonna be engagement agreements, fee agreements, discovery documents. A lot of discovery documents people are automating or streamlining. We also see a lot of motions as you mentioned. Then, on the transactional side, contracts, wills and trusts. Those type of documents as well. 

Chad Main:          That’s cool. Again, I appreciate your time today. If people want to learn more about Lawyaw, where do they find you?

Tucker C:           Yeah, absolutely. Thank you. If people want to learn more about Lawyaw, they can go to and you can also call us at 415-742-5600.


Does ODR Take Lawyers Out of the Process?

Chad Main:          Okay. Now let’s get back to our talk with Stephan Kane, the founder of FairClaims, an online dispute resolution platform. One criticism of ODR or depending on your point of view, maybe just really an observation is that at some level, online dispute resolution lessens the need for lawyers and may take the human element out of dispute resolution. However, Stephen doesn’t necessarily agree and points out that for many disputes, lawyers still may and do, and are necessary to participate in ODR.


Stephen Kane:       People are welcome to have an attorney represent them in any arbitration including with FairClaims. We’ve had plenty of attorney-represented claimants and respondents in the platform. I think that’s just up to each end user. For the end users who cannot afford an attorney or don’t want to use one, they don’t have to. For the ones who would like their attorney to handle matters, they can do that. Other people go and consult with an attorney as they’re going through the process and those are all open options.

Chad Main:          A similar critique of online dispute resolution especially as it relates to mediation, I think people might say to you, “Well, mediation is effective because it gets people in a dispute in the same room and there’s a human element, and the mediator can appeal to emotions and their reason.” But that might be absent when you’re using technology to resolve a dispute. What’s your response to that kind of critique?

Stephen Kane:       It’s not untrue and it depends on the type of dispute and the parties involved and the emotions, and we pay attention to all of that. We don’t believe that this is a solution for everything or everybody. We think it’s a different kind of option. We think there are trade-offs. It depends on somebody’s personal appetite for, do I want to get this done quicker? Do I prefer in person? We hear from some end users who say, “I don’t want to see that person.” Sometimes people want to and sometimes they don’t. Other people tell us, I don’t want to use FairClaims because I want to see the other side cringe in person and piss them off. You know what? It’s America, they have that right and it’s fine. It’s just trade-offs and what we try to do is we try to figure out what are the best solutions for certain problems? Then, optimize around that and we’re not trying to be the everything to everybody. In fact, we take a very small percentage of disputes from … with the companies we work with. 

With the marketplace companies, we’re an option of last resort. If they haven’t been able to work it out and they’re at an impasse, they either will do it where it’s voluntary or sometimes they’ve decided to include it in their provisions, but it’s up to the stakeholders involved. Our job is to be neutral, our job is to be open to everybody. Like you mentioned earlier again, anybody could use it. Other people will decide that for certain problems, they’ll decide case by case whether they use us. We’ve seen a lot of different approaches and we continually learn what’s best.


ODR is Taking Off in Europe

Chad Main:          Resolving disputes online is obviously not limited to commercial disputes, and is not always handled by private companies like Ebay, Amazon or FairClaims. Courts around the world are beginning to embrace ODR. For instance, consumers of any company in the European Union could submit disputes to the European Commission’s ODR platform. Closer to home? Courts in Los Angeles and other areas, offer certain litigants the opportunity to have disputes resolved online.

Stephen Kane:       There are several states and counties who have built a mediation platform particularly with small claims cases where they offer it as an option for people at some point in the process and it’s of course different in every place and that’s really wonderful. Look, I’m interested in people resolving disputes whether it’s through us or somebody else. I don’t care and I think it’s pretty cool. Then, yes, Europe has created some online dispute resolution standards. They have a product you can use to resolve disputes in Europe. England has done some interesting things where they’ve deregulated some legal regulation and allowed non-attorneys to invest in law firms. 

They are certainly experimenting and have been for the last couple years with providing online dispute resolution for insurance claims and by all signals, that’s going incredibly well where everybody’s better off. Because if you can just resolve things quicker, you free up more money and in the economy period. Then, if you can do it in the right way and thread the needles in the right way, which we try to do, then most, if not all stakeholders potentially could be better off depending on the decisions they make, their litigation strategy, et cetera. 


The Future of ODR

Chad Main:          As my talk with Stephen neared the end, I asked him where he thought the future of ODR was headed. He said, “One of the focuses at FairClaims is the resolution of non-monetary claims.”

Stephen Kane:       What we get most excited about are actually non-monetary disputes. The problems we’re solving now are big and especially with insurance claims. Getting money into people’s hands after an auto accident and having them feel good about themselves and about the result, that’s big, and building more trust within society. That’s really what this is about. But, we get excited about things like roommate disputes. Resolving those. I don’t think I’ve run into anyone who’s had a roommate and didn’t have some dispute, whether it’s monetary, non-monetary. I think with my roommates, like 10 years ago, one of our roommates was moving out and we had bought furniture together and the question was how much do we pay each other for the furniture? Do you diminish the value? We were geeks, okay? We were trying to figure it out and what’s fair.

It’s like, we figured it out. We figured it out amicably but we spent a lot of time on it and it was real money and it very well, very easily could have gone the other way. There’s certainly roommates who fight about rent and who’s gonna do dishes, and big and little things and that creates tension. Whenever there’s tension and stress, you’re not at your best and you’re focusing your time on things that you could be doing for yourself, for your family, for your friends that’s improving society. Roommate disputes is one example. Disputes between boyfriends and girlfriends. We as a team, early on when it was just three of us, we would go to small claims court just to ask people questions about what are you here for? We were able to do that of course all by the book. We weren’t soliciting them for our business at all. We were just gathering information. We were in the place we should have been, et cetera.

But we were like, “What are you here for?” It was interesting. There were like three people who were there, or at least two people we ran into and we visited a few times, who had a dispute against an ex-boyfriend and girlfriend about who was gonna get the dog, or who was gonna pay for something and reimbursement for a ring and stuff like that. We thought that’s really interesting because people are getting married later in life and there’s probably more of these. There was one time where I think it was through the Better Business Bureau who sends us some claims if people would like … and we’re partnered with the California chapter … where there were two or three roommate disputes in a row. What we noticed is that the conversion rate on the respondent voluntarily agreeing to sign up, because they can either have it pre-arranged in their contract or not, that it was higher than other areas.

We thought about that a lot and we said, “Well, maybe it’s because they know each other. Maybe they’re more likely to try to use something like this where they just need a little bit of a push.” We get excited about solutions on things like that.

Chad Main:          That’s very interesting and I never would have thought of that. It raises an interesting point then because I think if someone has a roommate dispute or a falling out with a significant other and they’re fighting over the dog, they might think for an instant, we could call an attorney for some advice, or I suppose they could go to small claims but that seems like a pain in the ass. I’m gonna do nothing. How do you, as the founder of FairClaims get the word out that there is a solution? There is a solution that exists that didn’t exist before and is cheaper and better and faster to resolve these kind of disputes that people may not take the time to resolve in the current day?

Stephen Kane:       We started working on dispute resolution with marketplaces, the home advisors of the world for specific reasons. That was we wanted to see a lot of disputes across a lot of different industries. They also are outstanding really early adopters who were willing to take a chance on me when it was just me with a Squarespace site. A couple of them, not most of them, who I was doing things manually because it was a problem for them. They recognized that there was value in people trusting them. They recognize that if they could resolve disputes quicker, they can enhance that trust. We started with them for that specific reason. With insurance claims, we feel like we’re solving potentially because we’re just getting started … a few months ago we rolled out our first proof of concept customer … that, that’s a big problem that we think people will talk to their friends about. We’ve already seen that happen with our marketplace disputes where we notice that once a year or so we get more in-bounds.

It’s been very slow going. It’s been four and a half years but, we think people talk about it. We think maybe folks like you are interested and then spread the word. What we focus on more than anything instead of getting the word out like with marketing, is building the very, very, very best product we can that solves big problems for people so that they might come back. Like when Starbucks just built … when they built beautiful stores and grew slowly. We’re in an industry, the startup industry that both evangelizes and worships hyper-growth. We believe there will be will a point where we hit hyper-growth, but we think the way to get there is by slowly and methodically establishing micro and macro trust with every single person who’s involved. And that at some point, enough people will talk about the result they got and look, some of them get pissed because they lost but at least people know it’s an option.

We do other things. We mainly reach out to influencers and stakeholders in law. We think the more lawyers who know about it, they can decide for themselves if it’s something they think is interesting, if they want to recommend it to a client.

Chad Main:          Yeah, I was gonna say that’s a great start is lawyers recommending to the clients because we’ve all had those calls. You talked about it earlier in the podcast. It’s a $2000-dispute. It’s not feasible for a lawyer to handle it and now they have a place they can refer their clients to. That’s a great point there.

Stephen Kane:       Absolutely. I always felt guilty when I had to turn people away. We think that over time … and I think we’re similar to Airbnb in that way. Airbnb was slow, slow, slow, slow and then at some point enough people talked about it that it became a thing. Look, we do things to reach out to groups and our investors are happy because we are selling enterprise software and I suppose services depending how you look at it to big companies now, where we can make money. We want to become the place people think about and go to when they have any kind of dispute once we gain trust in each category. Then, at some point, hit enough momentum in an inflection point so that it becomes more of a thing.

Chad Main:          That’s great and your point about Airbnb is very apropos I think because we’re talking about the change in mindset. With Airbnb it was like, “Why would I ever rent out somebody’s house or why would I rent out my house?” It’s real similar and with enough momentum it finally changed the way people look at staying overnight somewhere.

Stephen Kane:       Yeah.

Chad Main:          It could the same for what you guys are doing. It’s just a change of mindset and getting the word out that there is an alternative where one might not have existed before. 

Stephen Kane:       Absolutely.

Chad Main:          Cool, I appreciate your time, Stephen. If people want to learn more about FairClaims or get ahold of you, how can they do that?

Stephen Kane:       I’m on Twitter. Stephenlkane with a P-H. Stephenlkane. Feel free to DM me. We try to be as quick as possible. and check out the site. Hit me up on LinkedIn, whatever works for you.

Chad Main:          That’s a wrap for this podcast. As always, I really appreciate you listening. I would also like to say thanks to all our listeners who submitted our name to the ABA for consideration for their Web 100. We made the list for one of the best podcasts of 2018. That’s a nice honor and we really appreciate it. If you want to subscribe, you can find us on most major podcasting platforms such as iTunes, Stitcher, Google, iHeartRADIO, et cetera, et cetera. If you like us, I’d hope you give us a favorable rating. If you want to get ahold of me, you can reach me at That’s C-M-A-I-N Until next time, this has been Technically Legal.

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Episode 16: Vishal Agnihotri on Knowledge Management for Law Firms and Legal Departments

Our guest this time is Vishal Agnihotri, Chief Knowledge Officer (or “CKO”) for the Chicago based national law firm, Hinshaw & Culbertson. As CKO, Vishal is responsible for the firm’s knowledge management programs. 

What is knowledge management? Vishal has a great way of defining it: the ability to identify critical knowledge within an organization and then leveraging it to serve up at the right time for the right purpose.

Vishal explains that law firms are great candidates for knowledge management and that for law firm KM programs to succeed, CKOs must work closely with the firm’s Chief Information Officers and Chief Marketing Officers (CIO and CMO).

Vishal talks about her many responsibilities as a law firm CKO including keeping up with changes in legal tech, vendor management, making sure tools and software the firm already owns are used effectively and educating others about KM and related tools.

For law firms and legal departments interested in implementing a knowledge management program, Vishal says the first step is determining what constitutes “critical knowledge” and to use tools to organize that critical information. She suggests a good starting point is a collaboration platform to share knowledge and pose questions and to also utilize a good intranet for the organization.

To connect with Vishal, you can find her on LinkedIn.


Legal Founder Segment: Jeff Kerr of CaseFleet

We also talk to Jeff Kerr, the CEO of CaseFleet. A case chronology and management tool for lawyers that helps attorneys review evidence, organize facts, and identify trends in legal matters. Jeff also points out that CaseFleet is also used by investigative reporters and expert witnesses.

You can find CaseFleet on Twitter and LinkedIn.


Things We Talk About in This Episode:

Peter Drucker Knowledge Workers


Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI



Podcast Transcript

Chad Main: I’m Chad Main, and this is Technically Legal, a podcast about the intersection of technology and the practice of law, where each week we’ll talk to a different mover or shaker in the legal and technology field. We learn a little about them, what they’ve been up to, and hopefully get some real-world tips that will help lawyers better use technology in their legal practices. You just heard from Vishal Agnihotri. She’s the chief knowledge officer for the law firm of Hinshaw & Culbertson. In this episode we talk to her about knowledge management for law firms and legal departments. We also talk to Jeff Kerr, the CEO and founder of CaseFleet, case chronology software for lawyers.

In this episode we’re talking about knowledge management. What is knowledge management? In short, it’s a way for companies, law firms and legal departments to keep track of the information they collect in their day-to-day business. If ever there is an industry that has a use for knowledge management or KM, for short, it’s the law. The cornerstone of law is knowledge and precedent. Although when many think of lawyers, they might think of a stunning closing argument by a trial lawyer or a shrewd negotiator sitting across the conference table getting the best deal for the client, but as we lawyers know, the vast majority of a lawyer’s time is not spent on exciting verbal activities. In fact, the vast majority of time spent practicing law is doing the mundane, taking a look at the written word, reviewing legal documents, examining contract templates, or looking into laws handed out by governing bodies.

All this information used to be stored in file cabinets and books, but in the digital age, it is stored on computers, and there’s a lot more of it. This is why law is such a perfect profession for knowledge management. Despite what we want to think, not every legal matter cuts new ground or requires lawyers to come up with some new novel legal theory or create a new contract clause. Chances are really good another lawyer somewhere else, probably even in the same law firm or legal department, was hired before to address the same problem. This lawyer has notes, research or document templates that, again, could be put to use. But, often, all that prior knowledge is not that easy to find. It may not be organized, or it may not even be available. That’s where knowledge management comes in.

Our guest today is Vishal Agnihotri. She is the CKO, or chief knowledge officer, for Hinshaw & Culbertson. Although Vishal studied marketing, she got into knowledge management pretty early in her career. Before she made the jump to the legal industry, she worked at consulting and accounting heavyweights like KPMG and Ernst & Young. Vishal has a great way of succinctly describing knowledge management: It’s the ability to identify the critical knowledge within an organization, and then leveraging that information to serve it up at the right time for the right purpose.

Vishal: Knowledge workers, this was a term that Peter Drucker came up with. They’re workers whose main capital is knowledge. When you’re talking about accountants or lawyers or engineers or doctors, they all fall in the same category. Their work involves non-routine problem solving, and it involves convergent and divergent thinking. So, in both capacities, knowledge management is just about raising the corporate IQ, the collective intelligence of the firm itself, and the ability to build on each other’s ideas. So what we sell in a professional services firm is really between our ears. If you’re smart about it, you want to capitalize on what you know, what you’ve done before, so that you can make better margins going forward.

The purpose of a good knowledge management program is really to identify those key critical crown jewels of knowledge, if you will, that, when we leverage correctly, will serve for the firm’s benefit at the right time for the right purpose. Traditionally, this has been a very labor intensive process, so knowledge management was more about curating knowledge, gathering it, painfully, disseminating it for the greater good. We’re finding that that approach is becoming harder to sustain as we live in a world where information has just exploded. There’s an overload, if anything. So it’s giving way to an alternative approach that uses both technology and adaptive behavior to manage knowledge that’s internal to a firm, to manage knowledge that’s external to a firm as well.


Technology Begat Knowledge Management and Technology is Needed to Handle Knowledge Management

Chad Main: The interesting thing about knowledge management is that it’s kind of a thing solely because of technology. There has been an explosion of data as a result of the digitization of information, and you need even more technology to get a handle on all this digital information.

Vishal: We create, we curate, and we share digital knowledge in many more forms today than ever before, so firms end up needing a helping hand with managing all of that, in the service of their clients, with well designed systems that everyone understands and that everyone uses. I say uses because sometimes the scale and complexity of interactions between people and content can actually lead to increased business risks, so it is important that people understand how to use the systems, but they also have a fuller understanding of information governance and try to be compliant with that. All of this cannot sit on the shoulders of billable attorneys, and so they do need help with sorting through emerging technologies and evolving regulations around data.

So your point about, yes, somehow the electronic control and management of files of documents has led to some of this issue, and yet we turn back to knowledge. There used to be a time, at least when I started in this discipline 21 years ago, where piecing together information was the larger challenge. These days, that has become lesser of a challenge. What we face now is the challenge of filtering, of accessibility. I think, to some degree, people have started to undervalue information. They think it’s just abundant and it’s at your fingertips, but we know that that’s not the case. We have to make sure that you have integrated your systems well and you’ve employed better search engines, smarter systems, better filtering, and accessibility. Everybody wants it mobile, et cetera. So, yes, some of the problems have been created by technology, and we’re using other forms of technology to now address those.


Responsibilities of Law Firm CKO

Chad Main: So now that we have an idea of what knowledge management is, what does a law firm CKO do?

Vishal: As a CKO for a law firm, I straddle the world of business strategy and technology. I work very closely with the firm’s CIO, and my other partner in crime is the CMO. The CKO, like I said, introduces the firm to new tools, new processes, new idea that will enable faster and more effective access to useful, to actionable intelligence. I have a team that oversees all of the research, both legal as well as business research. We manage the vendor relationships for our digital research resources, print collections, et cetera. I’m also responsible for the vendor selection, implementation, training adoption of knowledge tools. This could be a knowledge sharing platform. It could be a smarter search engine, just integrating systems in order to be able to get to answers more effectively.

Even more important than that, while we are looking at surfacing the knowledge we have, because of the exploding legal tech landscape, there are lots of opportunities to automate specific, basic tasks. So what e-discovery tools did for document review, there are now so many other tools in the marketplace that are similarly automating some basic tasks, but changing the game very dramatically. That becomes our role to be sort of a technology purveyor, to go ahead and sort through the tech landscape and make sure that you find the right fits for your organization.

While we’re on that topic, a huge part of the role that I think nobody else necessarily has in the firm, or is at least expected to have, is keeping a lookout for new and interesting technologies. We talk about AI, machine learning, blockchain, et cetera. What are the new tools? What are the new technologies that are popping up? Is any of that relevant to our processes, to our workflows? Do we see them as things that can augment how we do things? Can they be possibilities for new service lines? Are they possibly threats to how we’re doing things? In terms of emerging technologies and both evolving regulations around data privacy, data practices, all of that is also a responsibility that the CKO has.


Law Firm CKOs Work Closely With Chief Information Officers and Chief Knowledge Officers

Chad Main: It used to be the only acronyms for business positions was CEO and CFO. Now there are quite a few acronyms hanging around the C-suite. As noted, Vishal is a CKO, or chief knowledge officer. In that role she works closely with the law firm’s CIO and CMO. That’s chief information officer and chief marketing officer.

Vishal: The CIO definitely offers, I would say … I’m going to use anatomical references here. The CIO definitely offers the backbone for the organization, so they’re not only making sure that the lights are kept running and the servers are humming and emails are sent the way they should be, with security and encryption and so on and so forth, and everything they do, in that sense, is mission critical. A lot of their work actually falls on the backend. A lot of times, I think, at the frontend, people don’t even know the extent of the work that’s going on.

In contrast, a CKO, a chief knowledge officer, does everything in the frontend space. So if they’re bringing in a new tool or a new technology, it is almost always to either bring the firm together. So, again, anatomically, if I reference it, it would be more like a nervous system, where you’re gluing everything together. You’re making sure all the connections are made, the dots are connected. Also, you can’t get away without making the main constituents actually use your tools. That’s the whole point. You cannot deploy it and then just hope that they will use it. You need to almost cultivate it, nurture it, make sure that they are paying attention, that they are using it the way it’s meant to.

There’s an element of adoption that is much more stronger, or an element of change management, I feel, that is much more stronger in a CKO’s job description, because you have to ensure that each user, each intended user, is using the new tool or is implementing the new process the way it’s meant to be. They may not get it the first time. There’s a marketing rule that says seven times you have to touch something to have enough brand recall. It’s similar. I think lawyers, paralegals are extremely busy. They have billable pressures. So in order to make a successful implementation, you absolutely need to make sure that they’re grabbing their attention and convincing them of why they should be using something, why they should change the way they’re doing something.


CKOs Must Educate Others

Chad Main: You just heard Vishal mention a couple of times that part of her job is educating others at her law firm at the tools and tech available to them. So I asked her to expand on that a little bit.

Vishal: The law firms make excellent cases, no pun intended, for the application of knowledge management. So one of the ways to explain to them how this works out is everybody is learning. Their entire job, their entire role as a professional rests on the idea of what they know, what they’ve learned. I don’t mean just what they learned in law school. Who knows what? Who knows whom? A lot of that is learned. It’s built upon. It’s interpreted in different ways. It’s managed, and it grows exponentially with their career. Some of it is lost to turnover. Not everybody grows up in the firm together forever. Some of it is just wasted, if you don’t capture it in any systematic way. Some will always be impossible to codify and share. But what we can share, and I’ve come to believe that a lot of the just-in-time knowledge that can be shared, can really, really change the game for them.

These are professionals who’ve spent a lifetime perfecting their craft. They get very specialized, very deep in a subject, and now they’re suddenly being challenged for even better service, quicker service, cheaper service, by the client. Knowledge management helps build that ecosystem of … We don’t expect partners to, on their own, take time, or lawyers, on their own, to take time and write down lessons learned from a specific case or some a-ha moment that they had. But as the knowledge officer in the firm, you can now build out the systems and bring them along in a way that makes it easier for them.

Under no circumstance can you build a system or create something for them that makes them cringe at the idea of knowledge sharing. So how do I educate them? A, by showing them that this is how other firms, other professional firms, have been doing it for decades now. By doing so, they’ve achieved better margins. They improve their not just marketplace value, but also wallet share with clients. Because the more you can codify this is what we do, this is what we’re known for, the more you can capitalize on that for future engagements, for future client relationships. In some ways, I think it’s not even rocket science. It can be uncomfortable, I will give you that, for law firms, for lawyers.

Chad Main: How so?

Vishal: So a lot of lawyers of the … I guess, trained many years ago, I think took the line, “Knowledge is power,” very seriously. I think, by that, they meant individual knowledge is power. My idea back to them is it is still power, but collective knowledge is even more powerful. So they are hesitant, sometimes, to put in the time or put in the effort or put in the mind share to help you with your knowledge platform, to endorse it, to participate in it fully themselves, largely because they’ve gotten this far without it, so they feel like they can continue to do so. But we don’t live in the same world that we did 20 years ago. Like I said, client expectations have moved. The marketplace dynamics have changed. So we really want to focus on what the marketplace looks like today and what works and what doesn’t work for today’s marketplace, for today’s client.


Legal Founder Segment: Jeff Kerr CEO of CaseFleet

Chad Main: Let’s take five away from our talk with Vishal, because now it’s time for our legal founder segment. This time around, we’re talking to Jeff Kerr. He’s the founder and CEO of CaseFleet, case chronology software for lawyers, and, as we will find out, software that’s used by others outside the legal realm. Jeff, thanks for being here today. Tell us a little bit about CaseFleet.

Jeff Kerr: Thanks, Chad. CaseFleet is a tool for creating chronologies of facts, and it’s designed for litigators and investigators, people who care about the facts and the evidence and who believe that mastering the facts of their case is the best way to win.

Chad Main: What was the inspiration for you to develop CaseFleet?

Jeff Kerr: So it goes back to my former legal practice. I practiced employment law in Atlanta, Georgia in a small firm setting, myself and my partner and a few associates. We didn’t have a whole bunch of paralegals to help us out on our cases, so we tried to leverage technology to do as much as we possibly could and to work our cases as well as we could without having a large team. I found that mastering the facts of my cases and knowing the documents and knowing the events and knowing the witnesses was the best way for me to get a good outcome for my clients [inaudible 00:16:26]. A lot of attorneys were a little bit sloppy about the facts, and if I just knew them well and was very faithful to the evidence, it really helped.

I found that the best way to do that was with the help of software of different kinds. Having a database, in particular, is essential if you want to create a real representation of the relationships between the legal elements in a case, the facts that you know, and the evidence that you’ll use to prove those facts. Those are three very important components to every case, and I think people underestimate the number of connections that there are, even in pretty simple cases. A database and a database-backed application is really the best way to organize that kind of information.

I wanted a tool to exist that I could not find anywhere, and I was somewhat proficient with technology myself, and I wanted that tool to exist so badly that I started writing code and developing some prototypes. I had so much fun doing that that I decided to make that my new job, and so I left practice of law in 2015 to work full-time on CaseFleet. That’s what I have been up to since then.

Chad Main: Did you write all the code and develop it yourself? Or did you hire a team of developers?

Jeff Kerr: I did not, by any means, write all of the code for CaseFleet. Throughout the entire history of the company, I’ve been working with developers and our CTO, who’s a computer science graduate from Georgia Tech, who understand best practices, and our professional coders, to create an extremely reliable and high-performing application. But because I have such a clear vision of the way I want certain features in the product to work and the different use cases that there are for a product like ours, it’s been very helpful for our team that I have been able to design and even implement some of the features, particularly on the front end of the application.

Chad Main: That’s cool. So I know CaseFleet’s got a bunch of different features. Can you tell us a little bit about those?

Jeff Kerr: The main feature in CaseFleet is what we call our facts page, and that is the place where you go to see what the facts are in each of your cases and to add new facts. Each fact can be linked to different people and businesses that are involved in the fact. A date can be assigned to it. It can be related to different legal issues that make it important or relevant in the context of the case. You can also attach evidence to the fact.

The second core feature is our document review feature. It really differentiates CaseFleet from a lot of other products that are in this field, in that document review is built in to the software. Our users, everyday, upload a great number of documents, which we index so that they can be searched for keywords, and also we allow those documents to be previewed within the same web browser that you use to access facts page and other parts of CaseFleet. That provides a huge benefit, because, as you review the documents, you’re able to extract facts from them in a very efficient way. So creating the chronology isn’t necessarily something where you’re having to write every single fact in place. You can build it from the documents themselves, such as depositions, interrogatory responses, and other documents that play a role in the case.

Chad Main: So, great. That sounds like a great tool. Who’s it for?

Jeff Kerr: We designed CaseFleet primarily for litigation attorneys, and litigation attorneys are the core of our user base. But we’ve found that it’s also been very useful for paralegals, litigation support folks, and other people on the litigation team, anyone who has in interest in reviewing the documents and ensuring that the facts of the case are mapped out in a really clear way. Another category of users consists of clients of lawyers who sometimes are the first people to buy the software and who want to organize their documents and different facts. We also have a good bit of use among investigators, investigative reporters, and people who provide expert testimonies for attorneys, such as forensic experts, forensic psychologists, medical records review folks. So it’s kind of a broad [inaudible 00:20:59] of uses that can be found for CaseFleet.

Chad Main: That’s interesting. I wouldn’t have thought about that right off the top of my head, investigative reporters and expert witnesses. That is an interesting use of it. Well, great. I appreciate your time today, Jeff. Where can people find out more about CaseFleet?

Jeff Kerr: The best way to learn more is to visit our website, which is, and, from there, you can sign up for a demo or access a free trial of the software.


Do All Law Firms Need a CKO?

Chad Main: Let’s get back to our conversation with Vishal Agnihotri, the CKO for Hinshaw & Culbertson. So do all law firms need a CKO? Not surprisingly, Vishal thought that most firms could use one, or at least could start thinking about formalizing knowledge management protocols. She pointed out that, by doing so, it forces law firms and law departments to examine their internal processes, which in turn might encourage improvement of those processes and boost productivity and client service.

Vishal: Any law firm or any professional service firm should have a CKO, if they are ready to implement the changes that will come with that kind of investment, so it’s a mindset thing. I will say this: Profession firms are very adept at serving clients. They’re very good. They hone the craft of looking externally, whether you’re talking about marketing or in terms of service, service quality. They’re very externally focused. I think what they sometimes neglect to understand is that building out a knowledge management program internally moves some of that focus to our processes internally as well. That could also be very beneficial in the service of the client. It could improve client service quality. It could improve margins and productivity for the firm itself. So, yes, a law firm should hire a CKO or should at least have a knowledge management program led by someone who can bring about both new ideas, improved processes, but also, frankly, raise the base understanding of everybody in the firm of new ways of working.

In a professional service firm, whether it’s a law firm or an accounting firm or an architect’s firm, you will realize that the client expectations are evolving every single year. They keep moving the goal post. Even if we are not willing to share collective knowledge, at a minimum, somebody’s got to be responsible for raising the professional intelligence of the firm itself. I can’t imagine that somebody who’s on a billable track has the time and the wherewithal to do that, so you almost need somebody to come in from a different discipline, like knowledge management.

Knowledge management is a lot about change management, thinking about how this human-computer interaction is going to take place. It’s a lot about looking at the marketplace. Some of it may be even pontificating, like looking at various scenarios. What would work out best? So being a little bit of a futurist, looking out a couple of years at the minimum. So they should have a formal KM program leader, largely because nobody who’s billable will have the bandwidth to do that.

Chad Main: There is also a business case for the implementation of a knowledge management system. It makes clients happy but it makes attorneys more efficient.

Vishal: So you could work on a number of documents and save them on your desktop and never share them with anybody else, and best of luck when you’re looking for something.

Chad Main: So legal documents, contracts-

Vishal: Right.

Chad Main: … pleadings or whatever?

Vishal: Right, client documents, your work product. Now, for example, you have a need where you’re looking for something. It’d be wonderful if you were doing the exact same kind of document for the exact same kind of client for 30 years, but that does not usually happen. So every now and then, you will run into a need where you’re looking for something. You’re looking for a piece of information. You could go back to the phone culture and pick up the phone and call 20 people before you get an answer. Or if you had a system where all of the work product was in one place, you had a very good search system that would search across, you would actually save a lot of time, instead of manually trying to go gather this information. Now you may still end up finding a document or two that you think are worthy, and you may still end up picking up the phone to the partner that created that or that has his or her name on it, but that is much more different and much less compared to the hours upon hours you would spend otherwise piecing together the information.

Clients, I don’t think, want you to have that luxury. They’re not willing to pay for research, that kind that you would do 20, 30 years ago, when they know that there are better tools out there right now. So they’re expectation is that you bring your A game on and you’re finding what you need to find as quickly as possible. In terms of dollars and cents, A, it’s great for your reputation in the marketplace. B, if you’re actually doing it in lesser time, the client understands that you’re very efficient. It may not be billable time, but I doubt if you were to spend six hours finding something whether you would try to bill all of that time anyways. In effect, it makes you more efficient and less burned out, but also you’re keeping true to the essence of client quality, and hopefully you’re improving your margins. So if it is a flat fee arrangement, if it is one of those alternative fee arrangements, then you’ve actually improved margins if you have managed to use a better technology to find something in a shorter period of time, as opposed to going at it with sticks and stones.


Where Legal Departments and Law Firms Can Start to Implement Knowledge Management

Chad Main: So we ended our talk with a question I try to ask all my guests. Where can lawyers start to implement the ideas they heard discussed on this podcast?

Vishal: First of all, I think, from a content perspective, you definitely want to understand what qualifies as critical knowledge in a law firm. I mentioned this earlier, that it’s a very laborious process to try to codify every single item, so you do definitely want to just focus on the critical elements. There’s also an element of timeliness. Sometimes you just need an answer to this question. So, right now, a lot of law firms will have pardon the interruption emails, where somebody has a question and they send it around to everybody, and everybody else is popping in to give an answer.

But what you really want to do is employ better tools that can help with that. For example, one of the tools that I had rolled out in my last law firm, and we’re working on it at my current firm as well, is a social collaboration tool where lawyers are able to ask a question. Others who think they have an answer are able to answer, and that Q&A is almost on a Facebook-like or a LinkedIn group kind of interface. It has a picture next to the person who’s replying, and it creates, if you think about it, a searchable repository of question and answers, with zero effort from anybody on the KM team. Of course, we implement the system. We make sure we remind people. We teach people how to use it, et cetera. But once that is done, you’ve now created an auto-building auto-populating … As the day-to-day questions pop up, the Q&A repository is being built. That’s a very good place to get started, because it’s just-in-time kind of learning. It’s just-in-time kinds of Q&A. It is very simple to use. It does not require a ton of training, and it’s relatively inexpensive to actually put into a firm.

Other places to start, for example, the research and library services report in to me. A lot of times you’ll find that the resources that we have that the firm has paid for are not fully utilized. I know it sounds like common sense. Why would they not use something that they’re not already paying for? But a lot of times we do have tool fatigue or training fatigue even. People pay attention for when they need it, and then they forget about it. So one of the roles that I take very seriously is making sure that the awareness level of everything that we have, that we subscribe to, is very high within the firm. So you can do that with your good old fashioned newsletters. If you need to add incentives in there, you can. But a lot of times, people will come back and say, you know what, I had forgotten about that. I’m glad you brought that up. Or, you know what, I attended a training session when it first came out, but it’s been a year since I’ve used it. So even though that may feel like a very small effort, it actually has a lot of returns, because the firm’s already invested in that tool or in that resources.

You want to have a good, strong intranet. You definitely want to have a good portal that … in a very simplified way, a bulletin board that sits, electronically, where you can go hand everything from the firms PTO policy to other firm-wide information, office locations, et cetera, et cetera. But that portal can also be made … It can be more than just a pointer to different applications. Here, I want to schedule a conference room, or here I want to check out the events calendar. It can be more than that. It can be an operations portal. It can have more items on that. It can be an operational dashboard. You can have the lawyers looking at their billable hours, at their WIP, et cetera. You could have more insight on specific clients, on your top clients, et cetera. So there are many ways to use that kind of hub, if you will. That’s important as well, to move people to a central location, especially if you’re operating with a small team.

Most importantly, you want to use all of these tools, also, in the service of building camaraderie and rapport within the firm. I know this sounds a little bit like HR’s role, and it is. I think knowledge management, as I mentioned, works as the glue of bringing people together. You’ll find that people share more or share better or share easier if they trust each other. So in a lot of firms where you have a lot of lateral acquisition, partners being brought in at direct entry level, they may or may not feel comfortable right away. Even though this feels like soft, mushy stuff, believe it or not, putting focus on building the camaraderie within a firm, not just within the office, but within a firm, across practice groups, across offices, is actually key to having a strong knowledge sharing culture.

Chad Main: So that’s all we have for this episode. If you want to get a hold of Vishal, you can catch her on LinkedIn. Her name is spelled V-I-S-H-A-L A-G-N-I-H-O-T-R-I. If you want to get a hold of me, shoot me an email at That’s We hope you enjoyed this episode, and if you want to subscribe, you can find us on most major podcasting platforms, like iTunes, Google, Stitcher, et cetera. If you like us, I hope you give us a good review. Thanks for listening. Until next time, this has been Technically Legal.


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Episode 15: Keith Maziarek on Pricing Legal Services

In Episode 15 of Technically Legal, we sit down with Keith Maziarek, Director of Pricing and Legal Project Management for the Chicago law firm Katten Muchin Rosenman. Keith discusses the evolution of his marketing and business development roles for two of America’s largest law firms into pricing and project management positions.

Keith explains that law firms are adding pricing positions because of economic pressures and client demands. Clients are demanding changes in the way they are billed (AFAs or “alternative fee arrangements”) and also demanding that law firms become more efficient.

Keith also explains how project management and pricing legal services go hand in hand because to properly forecast the cost of a legal project, a thorough understanding of how the work will be done and what resources are needed is necessary.

Keith notes that fixed fees are not the only type of AFA out there. He discusses fee collars and success based legal fees. Keith explains how pricing fits into law firm marketing efforts and why sometimes it is best not to bid on work at all if it is not a good fit for the law firm.

You can contact Keith here:

Legal Founder Segment: 

In our Legal Founder Segment we talk to Kevin Miller, the CEO of Legal Sifter, an app that uses artificial intelligence to help people negotiate contracts with speed and providing advice from company leaders and lawyers in seconds.

You can check them out on Twitter at @legalsifter.

Things We Talk About in This Episode

American Bar Association

Kellogg School of Management at Northwestern University

Keith’s Article on Law Firm Pricing Techniques

Alternative Fee Arrangements (AFAs)

Fee Collars

Carnegie Mellon Artificial Intelligence Department

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

Background photo above Christine and Hagen Graf


Episode Transcript

Chad Main: I’m Chad Main and this is Technically Legal, the podcast about the intersection of technology and practice of law. Where each week, we’ll talk to a different mover or shaker in the legal and technology field. We’ll learn a little about them, what they’ve been up to, and hopefully get some real-world tips that will help lawyers better use technology in their legal practices.

You just heard Keith Maziarek. He’s the Director of Pricing and Legal Project Management at the Chicago-based law firm Katten Muchin. In this episode, we’ll talk to Keith about the benefits of having a dedicated pricing and project management position in modern law firms and legal departments.

In our legal founder segment, we talk to Kevin Miller. He is the CEO of Legal Sifter, an AI backed contract analytics team.

This episode is about the pricing of legal services. You might be thinking a couple of things about that. You might be thinking: why does pricing need its own position at a law firm and what does pricing have to do with legal technology? No matter if you are a lawyer at a law firm or a client purchasing legal services, you are all too familiar with the mantra of more for less. Pick up any legal publication the last few years and you’ll read time and time again that clients expect lawyers to do more legal work for less cost, so what that means is lawyers must do their work cheaper and more efficiently.

That’s where tech comes in. Legal tech permits lawyers to become more efficient by automating certain parts of legal tasks and as a result requires fewer bodies on a project. Also, as Keith will talk about, tech permits lawyers to gather data about pricing which in turn helps those on both sides of the negotiating table and also provides crucial information about the time and effort it really takes to get legal work done.

As part of this more for less conundrum, clients are demanding creative pricing for lawyers. Sometimes you will hear people talk about AFA’s or Alternative Fee Arrangements. As a result, many firms are hiring people like our guest, Keith Maziarek, to fill newly created positions solely focused on pricing and process improvements. Keith didn’t start his career in legal. He started writing PR copy for his uncle’s company and then moved into the tech industry in the early 2000 where he started handling market responsibilities for a startup. Along came the crash and Keith moved his marketing skills over to the legal industry, where he got a job in the marketing department of the American Bar Association. While at the ABA, Keith figured out that the legal industry’s main trade association shared attributes of its law firm constituents. Specifically, silo departments and opportunities to create working relationships between departments.

Keith Maziarek: I worked at the ABA for a little over four years. It’s an interesting place to go into work from the outside because there’s a lot of people that are lifers there and you come in from the outside and make a lot of observations. You notice silos because you say, “People are here doing this? There’s people on the other side doing this, why don’t we all come together and try and mitigate some of the coordination issues and everything?”

So I started doing more than what my job was supposed to be because I would raise my hand and go, “Hey, you know what? Did we ever think about connecting those two things or making a more organized and streamlined approach to the way that the department does everything?”And they’d say, “No, that sounds great. Why don’t you go do it?”So I did a lot of those things and it was very interesting and got to be a very dynamic job for me after awhile because every time I’d raise my hand, they’d let me do other things. But what I started realizing over time was that from a career trajectory standpoint I didn’t feel like non-profit was where I wanted to be, but I had, in the process of being at the ABA for that long, I learned how to work within the context of the legal world, working directly with lawyers and trying to coordinate with them and weigh and balance different priorities that they have to get the input that you needed or get the participation you needed, those kinds of things.

I said, “Well, how is this a transferable skill?”And I said, “With law firms, there’s marketing jobs.”A lot of what I was doing was marketing and communications related, maybe I’ll try that.

Chad: After the ABA, Keith took what he learned about connecting insular, siloed departments within an organization and used that knowledge at two business development roles, with a couple of the United States’ biggest law firms: Akerman and DLA Piper. While holding a business development position at DLA, Keith also got his MBA at Northwestern and it was then that he really started utilizing his skills to help DLA cope with the changing nature of the way  legal work is done in the 21st century, the impact that technology is having on the law, and the changing client demands as a result of economic forces.

Ultimately, Keith’s role evolved into pricing and how to help law firms not only price their services to cope with client demands, but also how to manage legal projects and deliver value to clients.

Keith: When you work in a big firm like that, BD [business development], a lot of it is being a broker between people on opposite sides of the firm that don’t know each other exists, but they can offer each other something for their work.

Chad: Facilitator.

Keith: Yeah, basically. Yeah. Saying, “Okay.”And just kind of connecting those dots and being in a position where you’re kind of in a broker or agent type of position within the organization because you see across multiple silos or areas that other people don’t. That’s sort of a benefit of being in those positions and it sort of lends itself to being able to make those connections.

Chad: So do you ultimately get into a pricing position at DLA?

Keith: Yeah. So here’s what happened. When I was an undergrad and when I was in high school, I was always in AP Calculus and all those advanced quant classes and I said I want to get back into the analytical side of things and the quant side of things as opposed to just being more of the qualitative side of things that tend to focus on more of what we did in BD and marketing back then.

My three majors at Kellogg were Manager of Economics, Management and Strategy, and Analytical Consulting, which is basically big data analytics, predictive analytics, those kind of things. That was very calculated on my part, no pun intended. I wanted to actually focus on those things more and have those as the compliment to the other side of things where I sort of knew a lot about different businesses and different industries and what they were looking for from the legal services standpoint. That was a very deliberate choice that I made as far as what I wanted to focus on there. My thought when I went into Kellogg was,”I’m staying in legal.”I kind of liked the idea of going into management consulting.

What happened was, I started at Kellogg in 2007. When you go through the interviewing process at Kellogg, that’s usually in the fall and it was the fall of 2009. One of the worst times to interview in the last 15 or 20 years I’d say, other than maybe right after bubble, was during the financial crisis when nobody was hiring, right? People were laying people off in droves. It was hard. It was a hard time to interview with. It was much more competitive. I didn’t find a good path for me in management consulting to that process. I was thinking at that point 2009, 2010 I’m like … Or 2009 I’d say, yeah. I was like,”What am I going to do after interviews ended?”And I’m like, “I don’t know, what? I wasted all this time and all this money, what am I going to do with my life now? I’m going to be stuck in the same role.”Right around that time, the managing partner here in the Chicago office-

Chad: At DLA.

Keith: Yeah, at DLA, yeah. Bill Rudnick. Worked with him really closely. He’s a JD and a MBA. He’s an incredibly smart guy, incredibly gracious guy. He’s a friend and a mentor to me still. We still catch up from time to time.

He had closely followed my MBA studies and I worked with him very closely in the substance of the BD side of things for my job back at that point. He came to me and said, “Look. As a firm, we need to get our arms more around what’s happening within our industry because it’s changing and the way we do business is going to be different from now on. A lot of that’s going to come down to how we price our work, how do we create budgets, how do we deal with different technology opportunities that we have and implement those into the practice of seeing how we measure our work or how we’re more transparent with our clients?”All these things that are what actually came to fruition today. He’s like, “We need to learn about what we’re doing well, what we’re not, where we need to develop, and how we need to make sure we’re ahead of the curve on this.”

So anyway, long story short, he goes, “Do you want to be the co-founder with me internally of a task force that gets our arms around all these things and starts setting up a plan for the firm?”More or less. I said, “Yeah, I’d love to do it.”There was all these thing I want that would help me leverage what a lot of what of my studies were and also the environmental sort of awareness or information or knowledge that I already had from, not only the firm but also the industry. So yeah, that’s great.

Little by little from 2009 on I started getting more into the pricing thing and it was like, okay well, what are the different things clients are asking for? Are we doing those well? How are we measuring performance now? That to me … I was lucky because I started when a lot of other people started doing this in general and as I got more and more invested in it over time, I started trying to spend more time on that and less time on the BD stuff. Because I saw, number one, I was interested in it. It was intriguing to me. It was very rewarding to me. But then also at the same time I felt like there was a new profession developing out of this. So there’s gonna be a specialty. There might be an opportunity for me there.

So I wanted to pursue that a little bit and see if it turned into anything. I won’t get into all the gory details of the process but over time they said, “Look we need to create a formal function at the firm to develop these things into formal departments. Or whatever for they take but we need somebody to formally own it. Do you wanna be that person? We know you’ve got experience in it.”And I said, “Yeah, I’d love to do that.”

Chad: As noted, Keith’s position at Katten is Director of Pricing and Legal Project Management. In this role, Keith has both internal responsibilities to the law firm itself and also external responsibilities to the firm’s clients.

Keith: There’s internally facing work that I do and then there’s working with the partners, working with our internal departments; marketing, BD, finance, IT, all those things right? Enabling the functions basically, of pricing and LPM [legal project management], right? So you need data. You need different ways of getting reporting generated. You need different types of applications so you can generate certain types of analytics, and those kinds of things. So those are all very internally focused. Like, how does a company do any product development? Right? That’s an internally facing role, right? But marketing then puts it on the outside right?

So if you think about how those functions kind of, are symbiotic. Same kind of thing. So with what I do, you have to internally enable the analysis that you need and the types of reporting, transparency, all the infrastructure type, elements of the functions need to be dealt with, managed, developed, those kind of things.

And then the externally focused I was, “Okay, how does that present itself to the client? Either directly or indirectly?”It could be me saying, “Hey we generated these reports that show you a good birds-eye view. And then a little bit more in the weeds view of how our work is being done with you,”and where we see that there’s opportunities to look at different ways to price things, or efficiencies. So those kind of things are a very client facing thing to … Either that or just how I enable the partners to better interact with some of their business side counterparts, on the client side. To give them the tools or the information they need to be effective in those types of conversations as well.

So it’s kind of both. So pricing and LPM are the overarching disciplines, I would say. But then the way that those get done, or the way that those sort of manifest, have both internal and external versions, I would say.

Chad: We’re gonna step away from my chat with Keith for just a second. Now it’s time for our Legal Founders Segment. In today’s segment we talk to Kevin Miller. He’s the CEO of LegalSifter. LegalSifter is an AI based, contracts analytics tool.

Kevin, thanks for being here today. Tell us a little bit about LegalSifter.

Kevin: Thank you Chad. We really appreciate the interest.

LegalSifter has built a product to solve an age-old problem. Contracts are the most important, most prolifically used document in global commerce. And they’re just a universal pain. They’re hard to read. They’re hard to negotiate.

We’ve built a product that reads that contract and gives in-context help or advice, in a minute or two, to anyone who needs it; using artificial intelligence. And we think it’s a thing.

Chad: Tell me what was the inspiration to develop the app?

Kevin: Well the company was originally founded out of Carnegie Mellon University here in Pittsburgh, Pennsylvania. And if you live in Pittsburgh you know that Carnegie Mellon and Pittsburgh, is just a hotbed of AI activity.

I’ve personally been in and around AI for about 10 years. Our co-founders built a product for freelance software developers who never take their contracts to attorneys because they can’t afford them. And they said, “Hey upload your contract to this product and our product will review it and tell you what to think about protect you.”

And they did that way back in 2014. They got 5,000 people to use the product in a week. And then they put it on the shelf. They weren’t ready. The product was a beta. The leadership and the funding wasn’t quite there, or where it needed to be. They weren’t quite sure where they wanted to go.

I heard about the product about a year later. After it had been on the shelf for about a year. And I thought, “Oh my gosh, you’ve built a product that reads contracts and gives advice. That’s a big deal.”And so I jumped in.

We built a team out. And we had to get the use case quite right. We really wanted to partner with the legal community. It took us really, two years from that point to launch the product that’s out on the market today. And we’re proud of it. We think we built something that everybody is going to and wants.

Chad: Give us the elevator pitch about two things. What exactly LegalSifter does and it’s features. It’s unique features.

Kevin: Sure. So we’ll start with the primary users, and that’s for business. We’ll talk about how businesses use it and law firms use it.

So if I’m a business and I negotiate contracts all day long to run my business on the buy or the sell side. I typically have some combination of three issues. Either I have way too many people involved in the contract negotiation process. And it takes me way too long because, you know, “Chad you’re my boss and you’re on vacation. Then the lawyers too busy and the IT person forgot. It slows things down.”And that’s a challenge for typically middle to larger businesses, some small.

The second challenge people face, and the more common one, is that they have only one person reviewing a contract. Whether it’s a lawyer or non-lawyer. By themselves, reviewing a one to 100 page contract, and trying to represent that organization as best they can.

And then the third issue is really more on the solution that they have at their disposal. If you have inside counsel or even if you go to outside counsel, if you run your contracts through attorneys, often times it’s too slow and too expensive. Attorneys themselves don’t have technology that helps them scale or do a lot more in the same hour that they otherwise could. And so they look very expensive and very slow for the average transaction.

So you have some combination of too many people involved, one person reviewing a contract or it’s too expensive or too slow to go outside counsel. Well, the product that we’ve built empowers individuals to either negotiate contracts by themselves, take on more of the work. Thereby eliminating steps in that situation where you have too many people involved. Or if you’re by yourself, whether you’re a lawyer or a professional, you tend to make fewer mistakes and you tend to read product contracts faster with the product.

The adage is a person plus an algorithm is stronger than either by itself. If I have an individual reading a contract by themselves, and then I have that individual read that contract with LegalSifter, they’re gonna be faster, cheaper, and better. Meaning they’ll make fewer mistakes, get to a better outcome if they use the product.

And then finally for lawyers, and this applies to law firms. We give them the opportunity to become more efficient, to deliver things faster, cheaper, better. Which their clients are going to want. But we also, for law firms, allow them to put their brains and their best practices inside the product. Co-brand it and resell it to their clients. And open up new revenue streams on top of their typical full service, as spoke, work.

Chad: That’s really cool and usually the question I’ll ask the Legal Founders I talk to for this segment is, who’s the target customer? And you’ve already talked about, it’s law firms, it’s businesses, and it’s in-house counsel.

But when I was taking a look at your website today, before we hopped on this call, I noticed something pretty cool and pretty interesting. You also target accountants, sales professionals and others outside the law. Tell us a little bit about that.

Kevin: Most contracts on this planet are reviewed and negotiated by professionals and non-lawyers; Not attorneys. Because of the reason that I said before, and so what we’re providing is a way for attorneys to get their brain in the hands of those people at a cost and at a speed that those people can afford.

And we’re also providing a tool that those people can use by themselves, to empower them with a little bit of extra knowledge. To make sure that when they are by themselves, which is most days, that they’ve got that kind of in-context assistance that they need, to get to a better outcome.

Chad: Well Kevin, cool. Really interesting. Great product. So tell us where can people find out more about LegalSifter if they want to?

Kevin: is the easiest thing to do. Today, you can come on and learn about our product. In about four weeks, if the trains run on time … So this podcast is on October 11th, sometime before November 11th, you’ll be able to come to our website and try and buy the product. So that’s something we’ve evolved to over the first 14 to 15 months of the product … The products about 14, 15 months old. And we’re now ready to allow people to come to our website. To try the product and buy it, without even talking to us; come November.

So really, two ways. You can go and learn about it today on the site and then give us a call or send us a note and we’ll call you and let you try the product. In about a month, you’ll be able to do it without even talking to us.

Chad: Let’s get back to our talk with Keith Maziarek. The director of pricing and legal project management with the law firm Katten Muchin.

What do pricing and legal project management have to do with each other? A lot. As Keith explains, it is very hard to accurately figure out what you should charge a client if you don’t plan ahead and figure out all the steps that you need to take to get a project done, that’s where project management comes in.

Keith: Pricing and LPM go together. They’re sort of inextricably linked, right? So it’s sort of a process. So even if you don’t set a price up-front that’s based on certain assumptions, the way that the work is staffed is gonna impact that price. And later on that often comes up in conversations with the client. Which comes back around to pricing the next time, right? Because these are ongoing relationships.

And on the flip side, which is the way it more often will present itself, you price the work. But you price the work based on certain assumptions and based on the analysis that you’ve done of past matters and the way that you look at staffing questions and we’re you gonna use technologies to try and help enable either collaboration, or coordination, those kind of things?

All those things impact the pricing that you use to build a budget or workflow plan that you use in your legal project management process so they’re both sort of … It’s like a cycle. That they both go together, right? In fact, the funny thing is when I first started doing both of these things at DLA, there was a lot of price competition.

And clients were asking for alternative fee arrangements all the time. The partners would come to em and say, “Hey this client wants some other billing arrangement.”So we worked together and developed, come up with our set of assumptions and develop our pricing models from there. They’d come to me and say, “Hey that’s great. Thanks so much for the help. The client liked that fix fee that we did or that partial contingency, or whatever it was.”We did it as …

I would go to them and say, “Okay look, we need to use the plan and assumptions we put together now.”To track against what your actuals are. Because if you’re not following the plan, number one, we’re not going to be profitable. Number two, we’re gonna miss opportunities to communicate with the client and say, “Look, the scope has changed. Or there are other issues that have come into play that are gonna impact the price. “So we need to be very well coordinated on that. And nine times out of ten they’d say, “Yeah, yeah, yeah. I get it. I’ll come back to you in like a month once I get going. We’ll set up all that LPM stuff you’re talking about.”And you never hear from them again.

And then a year, year and a half they come back to me and they’d say, “Man I really got crushed on that deal.”And I’d say, “Yeah, you know why? Let me take a look.”So I’d look at how the work was done. I’d look at their staffing. I’d look at what ended up happening, and ask them a couple questions and I’d say, “Well, it’s pretty clear why you got killed on that from the realization or margin standpoint. You didn’t do any of the things that we put down in the assumptions. And that was what the LPM side was for. “And they’d go, “Oh, okay, fine.”

So that was a good, effective, but sometimes painful way of demonstrating what the value is of actually measuring budget to actuals. And the value of investing the time up-front to plan out how work is done. And then use that as sort of a blueprint to do it, and that helps you identify when things may be deviating. And with the reports that we can provide, we can help identify those deviations as soon as possible so you can address them with the client. Or the engagement team or whatever it might be.

Chad: So what you’re saying is, it’s a fool’s errand to come up with price without actually figuring out how the works gonna be done in the first place?

Keith: Yeah. The only time I wouldn’t use that as a blanket statement, there is some categories of work that are very market driven. But those are also highly patterned, sort of high volume ones. So it just is what it is. If you can’t do it for those prices than you either shouldn’t be doing it or you’re doing it wrong.

Generally speaking though, I would say yeah. You can’t just throw a number out there and say, “Ah I bet it’ll be this.”You also can’t throw out a half-baked number because a lot of times you have to understand what the nature of the data that you’re using as your reference point is; for modeling the new one.

So if you take something in a vacuum and you say, “Okay, I have a new complex M&A transaction that’s gonna be a cross border deal.”If you look at the last one, the last one might suggest a certain number. But it also may not be very highly correlated with what the actual attributes of this new matter are. So if you use that in a vacuum, which people would do from time to time, and they wouldn’t consider where they were similar and where they were different. And what the implications of where they were different would be, that gives you a very inaccurate estimate of what the numbers gonna be. All you’re asking for is trouble then.

A fool’s errand? If you have somebody like me or people in your finance department or whatever, that can go back and look at your data and break apart the numbers and give you some of these insights and go, “You know I see these levers. Tell me about why this happened. Or is this accurate here? Or is this relevant here?”You can put together that puzzle of what this new matter looks like, and know where you’ve got similarities and parallels. It’s well worth the time. Because just picking a number out of thin air or taking an average of a bunch of different, old matters is typically not as … You need more specificity and more accuracy than that.

And I’ve seen instances where partners will do that and they’ll say, “I think it’s like these.”And I’ll say, “Well, why?”And then I’ll pull the number and I’ll say, “Okay well tell me what it is that makes this new matter like any of these that we included.”And as you go through the list of the ones we included they go, “Well actually, you know what it’s different form that one. It’s different from that one.”So the nerd data guy in me goes, “All you’re doing is making a big noisy data set.”You’ve got a bunch of very unlike things in here that you’re trying to predict the future with. And that’s gonna give you a lot of variance with, so anyway …

It is definitely worth that extra level of diligence to go on the analysis side and understand better, at a very granular level, what is required. Or what you could or could not do. Or should or should not do, in order to come up with the best price possible.

Chad: We’ve heard Keith talk a few times about AFA’s. Those are Alternative Fee Arrangements. AFA’s are an alternative to the billable hour. Which is how law firms have historically built clients.

When clients approach lawyers about alternative fee arrangements, most probably think the client wants a fixed fee. Say I handle a routine contract negotiation for a set price. However AFA’s are more than just fixed fee arrangements.

Keith: So I break it down into three categories now. One of them I don’t really consider AFA’s. They’re just some variation on what the billable hour model is. If you define alternative fee arrangements as not hourly billing, then that last category is sort of in it’s own. I’ll get to that one. That’s my last one.

The first category is the fixed fees. And there’s obviously a variety of different forms of fixed fee. You can do for a whole matter, you can do for a task, you can do by phase. You can do by milestone, you can do annually, those kind of things. So those are sort of, all the varieties of fixed fees.

The next category I use is more of the risk-sharing. The more ones with the contingency of performance element. Right? So it’s sharing the risk and sharing the reward with the client on a … Usually on a higher level. I don’t wanna say higher level but from a different perspective than a typical fixed fee would be. Example being like, a partial contingency.

Sometimes you’ll use a flat fee and say, “Okay. Based on outcome.”There’s some other supplemental piece of compensation the firm gets. And if it’s a good outcome, based on the magnitude of the good, I’ll say, right? We get a bigger and better reward or portion of that. And if you hurt, than we’re not going to disproportionately profit from, what would be considered a failure for the client. We want to be in this with you. So that’s the second category of the contingency related ones.

The third category are the ones that I say I don’t consider them true AFA’s. But they have a place. But at their core, they’re still measured as a function of hours times rate. That’s things like the fee collar. Which definitely has a place. Those are very interesting. I used to be in love with the fee collar.

Chad: Which is?

Keith: It’s basically … You go through a very similar exercise of setting a fixed fee but rather than just saying, “Okay. This fixed fee is either set in stone …”What you do is you say, “If it’s within 10% above or below, based on some agreed hourly rates and the hours that we bill.”We’ll charge the client whatever that number is that we agreed on.

If it falls outside of that it’s usually a scoping issue. The scope was less than we thought it was gonna be or more. In which case we have to make some other accommodation and there’s a whole spectrum of other accommodations that can be made.

Now I don’t have a problem with that but it still does come down to you’re going, “Okay. What is an hourly rate assumption that we use for each timekeeper?”Which has gotta be based on some discounted number, typically. Or even if it’s a full freight number. To come up with what that range is gonna be. And so that is not exactly what I would consider to be like … It’s not a fixed fee anymore because it’s somewhat variable based on what that is.

Whereas in a true fixed fee, you wouldn’t measure things as a function of time and rates. It would just be, “Okay based on our experience in the past, what do we see that this is gonna be?”And regardless of slight changes, what does that mean?

So the other ones that I don’t consider to be true AFA’s, that was the first one. Just to round out the explanation there. Volume discounts, things like that. Like blunted rates, a blunted rate really isn’t an AFA. It’s still a rate times hours. And if you do it right, it’s a function of what you assume your staffing makes to be in those kind of things.

So they are different tools and they’re different ways of packaging your pricing. And the work, as far as how you go to market with a client. But in terms of what the more accepted or traditional definition of alternative fee arrangements is, they’re not … They still are based on hourly rates times hours. So that’s why I don’t consider those to be true AFA’s.

Chad: Keith wrote a great article for the ABA Journal about pricing legal services. I’ll put a link to that article on the episode page at Be sure to check it out. A lot of good information in that article.

In the article Keith talks about the four P’s of marketing. Promotion. Placement. Pricing, and Product. Before reading that article, I hadn’t really thought of prices being that much of a component of marketing.

Keith: The four P’s I think are more traditionally thought of in like the CPG [consumer packaged goods] context, or that kind of thing, like products. As opposed to services or high-end differentiated services like legal is. But it’s still a model that applies.

Price is one of the four P’s because the other three P’s can impact what your price is. Right? So product … In our case it would be service, not product, right? But is the work that you’re pricing more commoditized or routine and there’s high price competition? A lot of different competitors and substitutes that you could use to do it? Or is it very bespoke type work where the people that you have at your firm, are very specialized in these particular skill sets. Or these areas where they have a very unique value, very differentiated value. And that helps you protect your pricing power, right? So that’s the product side of things.

Placement is another thing. Where do you fall, I’m just thinking in the legal industry; from that perspective. Where do you fall within the continuum of firms? Are you a global firm? Are you more of a local firm? Are you mid-tier? Kind of one of those things? And what are the right types of clients or work that you’re going to pursue based on what your placement is within the industry. Right?

So promotion is really, in a lot of ways … I think of the way that we articulate the aspects of what our placement and what our product, or our service are. Right? So again, if you’ve got … Think about the old adage, if a tree falls in the forest and nobody hears it, does it make a sound? If you’ve got the most specialized person in the world but we’re not … Either they or we as a firm, are not good at telling the story and demonstrating and articulating to clients why this person is the greatest at that they do. And what particular advantages or benefits that promises to them as clients so that they work with us. If we’re not good at promoting that in a way that’s gonna be helpful, then either we’re not gonna get the work or we’re not gonna be able to again, impact the pricing power that we have as we price the work. Right?

That to me is how the model overlays in the legal industry. In terms of how those different disciplines interact with each other.

Chad: I asked Keith what he would say to a law firm legal department that is kicking around the idea of hiring a pricing specialist.

Keith: The types of questions and the demands, the nature of the demands that clients have had is they’ve developed more sophisticated ways of analyzing what their spend is, where their spend should be, who they’re using and what’s generating that spend. Those kind of things. They’ve gotten increasingly sophisticated in the questions they ask and the demands they make of the law firms that they work with. And those things are becoming pre-qualifying, prerequisites for whether or not they’re gonna work with the firm.

So someone in a pricing LPM type position or with that skill set, is very well-positioned to help not only, interpret what those needs are but then translate them into, “Okay, I can make those actionable strategies for the firm.”

I’m not saying anything that I haven’t heard from dozens of partners over the years. They didn’t go to law school to do math. A lot of these things that relate to, what are the metrics we’re looking at? Or how do you interpret some of the figures you have over large portfolios of work, and those kinds of things? That’s not something within their sweet-spot or what their comfort zone is. So to have somebody that is more versed in those things, and in those areas and can bring that to the table; it’s a big advantage when working with clients that are asking for some of these things. Or their outside, again, of the traditional comfort zone or scope of what a typical law firm partner would be doing.

Chad: So let’s say that the firm’s not quite there yet. Are there things law firms can be doing regarding pricing, without a dedicated position like you hold? And if so, what should they be doing?

Keith: If you’re not gonna create a whole new function for it. Leverage the ones that you have. The ones I’m thinking of most are typically, in most firms like your IT department, and your finance department. Or accounting or billing, it could be … Depends on how you’re structured. Where those fall.

But data is the biggest tool that we have in the arsenal to go, “Okay, when clients are asking me about these things and I haven’t really looked at these types of challenges in a different way other than billable hours in the past … “Looking at leveraging some of those people in IT to go, “Okay, what tools do we have that can help generate some of these reports that maybe our client’s asking for.”And that can be a learning process internally as well. To go, “Okay the client asks for this, let’s pull it together. Let’s interpret that on our own.”And say, “Oh you know what, I understand what they’re trying to get out of this, or I don’t.”In which case that can initiate a conversation with their client as well.

But back to the original questions, leveraging what you already have to understand better how your work is being done and how that coincides or doesn’t coincide with what the client’s priorities are. So you’ve already got a lot of that information resident within your firm. It’s a matter of tapping into the resources that can get it for you. Again, that’s usually the people that deal with the numbers and people that deal with the tools that hold the numbers, and can spit them out for you.

So getting close with those and trying to get those initial steps down of understanding better from a practice standpoint, from an office standpoint, however you’re structured. From a partner, each partner, or billing lawyer standpoint. Where you’re seeing the most revenue. Where you’re seeing the staffing models, coming up and down. Understanding better how, again this is sort of a data driven thing …

Profitability has been the new mantra within the community of people who do what I do for probably at least seven, eight, or nine years now. Understanding better how you make profit as opposed to just how you make realization. Those will help you make different decisions as well.

So you can work backwards from PPP [profits per partner]. And everybody’s measured those internally so working with the CFO to understand, “Okay. On a more individual practice level, how are we generating profit?”And how does that work from timekeeper to timekeeper? From client to client? So getting a better awareness of what those parameters are, just as a general understanding.

Again, these are things that should exist somewhere within most firms. In some level of sophistication or another. So being able to just get started on, what are those key metrics that we can use to measure how we’re doing, what we’re doing, and what means success to us and what doesn’t? Leveraging those in a way on a day to day or a month by month basis for my business, those are I’d say, some the easiest first ways to do it.

I think once you start down that path, you usually get one or two adopters that will start to get really into it. You always get several people that are invested in it. They get curious and they go, “Oh you know what I was thinking about? Let’s look at this. Let’s look at that.”And they’ll find some success. And those are people that’ll bring those stories to the forefront internally. And that’ll help build momentum or awareness and hopefully get to the point where you do wanna build a function like that.

That’s how it works with people like us that do this as our full time job. It’s really trying to find and make those compelling internal cases. And then scale them as much as you can. That will happen on it’s own organically as well.

Chad: As I left Keith, he offered a great piece of parting advice. He pointed out that part of his job is to help lawyers figure out that sometimes the best pricing is none at all. That is not even bidding on work if it’s not a good fit for the firm.

Keith: Doing every piece of work that’s put in front of you, regardless of price isn’t always worth it. It shouldn’t be worth it. There should be more of a strategy behind what you’re doing. I know this is easier said than done. A lot of times it’s harder to turn away work when it’s kind of on your doorstep. But it’s one of the things that, again the increased focus on profitability … Have a solid and agreed upon profitability model. You’ll know when something’s not profitable anymore. And it’s okay to do some work that’s not profitable as long as you’re doing other work that is profitable.

So people always will say, “Well, at least I’m helping keep the lights on.”Right? This is a loss-leader. Well if you look at somebody’s book of business and 90% of it’s loss-leaders, that’s not-

Chad: It’s loss.

Keith: -leading to anything. It’s a loss, right? So-

Chad: A loss.

Keith: I always say that … I don’t know if I made up this tongue twister or not but a loss-leader is only a leader if it leads to something that’s not a loss. That’s what I tell them all the time. You can do a loss-leader and that’s good. And that’s got client value from a financial standpoint as well as a relationship standpoint. If you’re not balancing that out with something that’s more specialized, and more profitable, then you need to kind of reassess why you’re doing those loss-leader type things.

So that’s one reason why it’s not worth bidding on everything all the time. The other thing is, clients have different tactics of either collecting information or using information that’s collected as leverage. In their negotiations either with you or with other people. Just be mindful about, that the rate information you send or the bid you give out or the amount of discount you’re willing to give them. Doesn’t go away like a puff of smoke and it never … It doesn’t disappear. That’s captured in time forever. And they’re gonna use that somewhere right? You’re setting an expectation.

Chad: And I think your point there is … And it has nothing to do with whether you should or should not do the work. Make sure your bidding on a project that you actually have a chance because maybe the bid is requested to just get competitive intelligence.

Keith: Sometimes, yeah. Yeah. Yeah. Well, yeah. I’ll give you an example. So sometimes big RFP’s will come from companies you’ve never done work for. It’ll come to a partner that never met anybody at the company. And one of the qualification questions then is why do you think you got this? If you’ve never done work for this company and you don’t even know anybody there, what is the point of us spending all this time to put together this proposal and this response and all these bids and everything? The probability of us ever seeing a dollar, let alone a profitable dollar from it, is pretty low. So you gotta think, “Okay, why would the client send me that?”It’s probably either because they just had to get other bids and they already knew who they wanted to pick in the first place. Or they’re collecting market data that they’re gonna use from an organizational or an institutional standpoint on, “Okay how are different firms in the market priced? And how do we start base-lining those things?”

The other thing is sometimes they’ll … If you get an irrational bidder, which I’ve been part of those things too. Where you try to give the best advice possible but there’s a belief that if you just give the biggest discount, that it’s all gonna be worth it in the end. Clients will anchor to that and they’ll say … Either they’ll come back to you in the future and say, “We expect that same level of discount because you offered that before.”Whereas that might not be a sustainable thing or that might not fit the new piece of work that you’re bidding on as well as it did the old one.

Or they’re gonna go back to their other firms and say, “Oh well, we’ve got competitors of yours that are bidding 25% less or 30% less.”And that’s information that can be used … It can be leveraged in a way that can be advantageous in a very one dimensional way. So just being mindful of those kinds of things.

The other thing is too, and this is more negotiations, if you put in a bid and you get a response like the one I just mentioned. Like, “Oh we think you’re great but all your ‘competitors’ are 25% less than you.”You have to kind of ask them questions as opposed to just taking … Don’t be an order taker, make it a negotiation. Right? So counter that offer. Don’t say, “Okay.”If you know you can’t do it for that cheap, or you shouldn’t do it for that cheap, there’s a good chance that any of your direct competitors aren’t offering it at that price either. The client is coming back to you and trying to say, “Okay what can I extract out of this? Get the best price I want.”

And that’s their job. They’re always supposed to say, “Can you do it cheaper? What’s the cheapest you can do it for?”Totally understand and respect that. It’s our duty on the law firm’s side to play the … Be the same steward to our firm, and to our book of business and say, “Okay, if you tell me other ‘people’ will do it for 25% less … Man, I would love to have this work and I wanna meet you in the middle here but I can’t do it for that. How about 10% less than whatever it is?” Obviously after some careful analysis of what you could afford to do it for. But don’t just assume that a counteroffer is a walk away offer from the client and you can’t engage in a … I’d say a fair and reasonable negotiation process to come to a point of agreement that works for both sides. You always want win/win’s.

Chad: Cool. Appreciate your time.

Keith: No, hey thank you.

Chad: A lot of good info. Lot of good info there. So if people wanna contact you, where do they find you?

Keith: You can find me … I’m all over LinkedIn, or email is: first name dot last name. So K-A-T-T-E-N-L-A-W dot com. I’m out there.

Chad: So that’s all we got for this episode. We thank you for tuning in. If you wanna subscribe, you can find us at most major podcast platforms like iTunes, Stitcher, Google Play. If you like us enough, please give us a five star rating. If you wanna get a hold of me, you can find me at That’s C-M-A-I-N-@ recipient dot C-O. Thanks again for listening. Until next time. This has been Technically Legal.

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Episode 14: Barry Solomon on Legal Marketing and Technology

Marketing. Not always front and center for lawyers and law firms–but it should be.

In Episode 14 we discuss legal marketing with Barry Solomon, lawyer, former BigLaw CMO (Chief Marketing Officer) and current President of Foundation Software Group. Foundation develops law firm experience management software providing a foundation for other knowledge management applications that need to know what the law firm has done, who did it, who it was done for and who all was involved.

Barry distinguishes legal marketing from business development and explains how the two should work together. Barry says the key to good business development is to really listen to clients about their needs.

Barry also discusses the benefits of using of technology to gather data and track marketing metrics. He points out that much of the data helpful to improve marketing efforts is often found in software law firms already use (such as billing and timekeeping software, matter management software and the like).

Barry’s tip for law firms wanting to get serious about marketing but still testing the waters is to have two programs in place: 1) a program to gather client feedback; and 2) a program in place to train lawyers how to develop business.

You can contact Barry at and learn more about Foundation at


Legal Founder Segment: Daniel Goldstein of Trust & Will

In Episode 14 we also talk with Daniel Goldstein, the Founder of Trust & Will, an online tool to create, edit, store, and share a trust and will. To create a will on the site, users need only answer a few questions and decide what type of estate planning documents are best for them.

Daniel can be contacted at


Things We Talk About in This Episode

Interface Software

NITA – National Institute for Trial Advocacy


Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI




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Episode 11: Lucy Bassli on The Modern Legal Ecosystem and Unicorn Lawyers

In Episode 11 we talk to Lucy Bassli founder of InnoLegal Services and Chief Legal Strategist at Law Geex.

Lucy started her career in Big Law (at Davis Wright Tremaine) and ultimately landed a job in Microsoft’s legal department where she served as Assistant General Counsel. At Microsoft, Lucy was responsible for, among other things, the legal department’s procurement operations and contract management systems.

Lucy left Microsoft in 2017 and started InnoLegal Services–part law firm and part consultancy–where she helps law firms and law departments develop new ways to deliver and receive legal services.

In her role as Chief Legal Strategist for Law Geex, Lucy advises on the use of artificial intelligence in contracting, helps with product roadmaps, consults with corporate customers, and assists with the development of go-to-market strategies.

During our talk, Lucy explains who the players are in the modern legal ecosystem (regulators, industry groups, service providers, consumers of legal services and educators) and why to be really successful and efficient, all of them should work together.

She also explains what it means to be a unicorn lawyer–a lawyer that knows law, but also loves, understands and values process and technology.

We also talk about the “Big 4” entering the legal market and how law firm associates have a real opportunity to push for change.

Lucy can be found on LinkedIn and at


Legal Tech Founder Segment: Nehal Madhani of Alt Legal

In our legal founder segment, we talk to Nehal Madhani, founder of Alt Legal. A docketing system for intellectual property matters. You can follow Alt Legal on Twitter or contact Nehal at


Things We Talk About in This Episode

Lucy’s Articles on the Legal Ecosystem
Suffolk Law School’s Legal Tech Certificate Program

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI




Chad Main: For episode 11 we talked to attorney Lucy Basilli about the modern legal ecosystem and what it means to be a unicorn lawyer. Lucy recently left the legal department at Microsoft where she served as Associate General Counsel. When she left she founded a consultancy and law firm called InnoLegal Services. Lucy also splits her time with contract automation company, LawGeex, where she serves as Chief Legal Strategist.

Also in this episode for all you intellectual property lawyers, we talked to Nehal Madhani about the company he founded, Alt Legal, which is a docketing system for intellectual property matters.

Chad Main: I was pretty excited to land Lucy as a guest for the podcast. The first time I heard Lucy speak was last year at the CLOC annual conference. CLOC stands for Corporate Legal Operations Consortium. Among other events, it has an annual meeting once a year. For the last couple of years the annual US meeting has been in Las Vegas.

If you’re in legal operations or just want to learn more about legal ops, I highly recommend you looking into CLOC. When I heard Lucy speak at CLOC last year, she was still in-house at Microsoft where she was responsible for a bunch of things including implementation of the legal department’s contract management system. She was on the panel with a bunch of other legal ops bigwigs and the topic was on how to really change the way the legal industry does its work.

On the panel that day Lucy said something that really resonated with me. She said that for modern lawyers to really do a good job and deliver value to their clients they are going to have to embrace and work with others who are not lawyers, but have other very valuable and important skill sets.

Lucy Basilli [Excerpt from CLOC session] I think there’s another fundamental shift that needs to happen. I think those few practicing attorneys who are in here. Those of you who are recovering attorneys don’t hide it, we need to embrace all of the other professionals that are in this ecosystem, because without them we will not be able to move the dial.

That’s a fact. I did not research. I have no backing, but you’re going to have to trust me on this. It is a fact that we can not continue to function in our “lawyer versus non-lawyer” world … Who hates that word?


Chad Main: What is the legal ecosystem? It’s a group of various key players that serve the needs of legal clients. Some of these players provide what we would consider traditional legal services. But others, they provide very important legal related ancillary services.

As in most industries, you gotta have regulations, and that’s where Lucy thinks the legal ecosystem starts. On a side note and by complete coincidence, Lucy is writing a series of article about the various players in the legal ecosystem. I’ll throw up a link to those articles on the episode page for this episode, episode 11, on [Links to articles above].

Lucy Basilli: I think there are a number of key players that together make up this ecosystem, which is very gently and sometimes not gently disrupting each other and forcing each other to change and try new things. If you just go along the cycle of ecosystem or spectrum, however you want to look at it, there are certain regulations, of course. There’s a regulatory body or sets of rules by which attorneys have to practice within the US. Let’s just focus on the US because if we go outside it becomes even more complex. But in the US we know we have 50 states and each of those 50 states has their sets of governing rules of how lawyers should practice. It just addresses lawyers. But what it does is create really the boundaries of the practice of law, and at the same time the confinement of the practice of law and keeping others out. That’s one key player.


Chad Main: I didn’t really think about it until my conversation with Lucy, but another key group of players in this modern legal ecosystem are industry and trade groups like the one I mentioned before, CLOC.

Lucy Basilli: Another key player that is certainly becoming more and more notable and listened to I think, are the industry groups. Whether it is CLOC, the one you just referenced, or Association of Corporate Counsel. They have a legal operations group now. There’s more and more happening at the ABA and the Law Practice Management Division, or even parts of the Association of Corporate Counsel that aren’t legal operations. Of all of these, whether it’s legal operations as a general umbrella, or law practice management concepts, these professionals, or the attorneys who are taking on these new roles, they’re all coming together at a greater pace than ever before. They’re forcing conversations and sharing practices and ideas that is also overflowing into impacting the service providers that are part of the ecosystem.


Chad Main: Now we get to the group of players in the legal ecosystem that are very near and dear to my heart, the service providers. Service providers can be law firms, they can be tech companies, or they can be alternative legal service providers. The first two are probably familiar to you and exactly what you think they are, but the latter, alternative legal service providers are sometimes known as legal process outsourcers or LPOs, are fairly new to the legal industry. They’re companies like the one I founded, Percipient, that work with lawyers and their clients to accomplish important tasks that may or may not be viewed as traditional legal work, but work that is without question, very important and necessary to getting modern legal work done.

Lucy Basilli: Shifting to the service providers there are a couple of key buckets that. One of course are the law firms. Two, will be the legal tech service providers. Three, will be the alternative or legal service providers, or legal process outsourcers, or legal services companies. There’s a lot of names, one of which I will disagree with. I hear law company out there a little bit now, and I don’t think they actually are doing law. I think they’re doing services, but I digress. Then, the last one, I’m kind of giving it its own category, although I’m not sure it does need one, but I think it’s starting to become one, are the Big Four. They are who they are. They don’t need naming or listing and they are a key player right now in the ecosystem.


Chad Main: Last but not least in our tour of the legal ecosystem we run into the legal departments and law schools, the purchasers of legal services, and the educators of lawyers.

Lucy Basilli: Then of course, we have two other key constituents in the ecosystem. One being the corporate legal departments which are the procurers of the services from those groups that we just listed. Finally, we have of course law schools. As you can see this is a chicken and egg cycle. I don’t know where it starts, and we don’t know where it ends. But all of those players are impacting each other. Actually I just launched a series of articles through Thomson Reuters and their legal executive institute that looks a little bit deeper into each one of those, because it is a fascinating time we’re living in and all these new players working together, and some of the old players that are feeling the pressure to change how they play the game.


Chad Main: Before I got to Lucy’s take on why it’s important for all members of the legal ecosystem to work together, I wanted to talk to her a little more about the impact that the Big Four will have and are currently having on the legal market. As the Big Four try to claim their piece of the legal services pie, they’re a good example of how and why lawyers must work with other disciplines to provide true value to clients.

Lucy Basilli: They, like the legal services companies, or the alternative legal service providers, whatever is the best name for those growing companies, like them, they’re pushing the envelope on the definition of the practice of law, in the US for sure, because again, we have some boundaries that are pretty clear and finite, on one hand. On the other hand, there is a spectrum of work that lawyers do that many are arguing really isn’t the practice of law and that you don’t need a license to do. If you don’t need a license, you’re probably a lower cost resource, which is why the alternative legal providers have done so well in the last decade plus.

The Big Four have picked up on that very quickly, so they have their own legal services that they’re providing that are again, not the practice of law in the US, but very close. But in addition to that what they have, what their bread and butter has been for so long is fantastic management consulting skills. Something that the ALSPs are now doing and adding and have been developing. But the Big Four, that was inherent in who they are and what they’re good at. They already have contact into all of the major corporations. I do mean all. Every major corporation is using one of the Big Four for something.

Lucy Basilli: In addition to that, the amount of marketing resources that they have, and how they do their marketing goes well beyond any alternative legal service provider or law firm. Layered on top of that, are the resources that they spend on R&D. They have significant budgets for R&D. If you put all of that together, they’re finally approaching the sleeping giant of legal, that they hadn’t approached maybe for some time and it was safe for law firms to have the lion’s share of the work, as the ALSP started to grow and eat away at some of that law firm work. But more so, the ALSPs, alternative providers were really going after the in-house work that was still not being sent to firms but really bearing the in-house lawyers. That was their sweet spot. Law firms continued in their same sweet spot that’s been historic and the same for gosh, decades.

Lucy Basilli: In comes this new entrant that’s bringing in very highly skilled attorneys who actually aren’t practicing law, but have the benefits of being with a very reputable and prestigious firm, one of the Big Four, bringing in a variety of other skill sets from their consulting side of the house, from the solutions architects experts, throwing on top of that R&D resourcing, throwing on top of that good marketing. There’s this whole mix that they have put together that’s very natural to them, but it’s newer to legal. I see them as a really big threat. Their more direct threat in the US as they start to open up these kinds of special relationships with a law firm where they again, aren’t practicing law but they’re engaged with a law firm of some sort, and these other nuanced and creative corporate entities and structures, where they’re still within the rules of not getting into the unauthorized practice of law in the US, but finding ways to deliver a service that is very close. They are a uniquely positioned set of resources, each one, that bring together, I think, the best of what the ALSPs, the law firms and the legal tech providers have.


Chad Main: Now that we’ve discussed all the various players in the legal ecosystem we get to the “Why”. Why they should all want to and why they should work together. As Lucy explains, it boils down to increasing the value lawyers provide their clients, bettering the client experience, helping clients further business goals based on the legal advice they receive from their lawyers, and also it helps lawyers and clients actually implement the legal advice they receive from lawyers. It’s this latter part, the implementation where a lot of other players for legal ecosystem can really help attorneys.

Lucy Basilli: Law firm lawyers, they need to expand their horizons of the value that they’re offering. At the end of the day, the value can’t continue to be, that I’m the best litigator, or I’m the best negotiator of contracts, or you name it, regulatory expert, because there’s more needed from the in-house corporate legal departments than that anymore. The complexities that companies are dealing with and the complexities of then the legal teams in-house are dealing with require different sets of skill beyond just the traditional legal subject matter experts.

Lucy Basilli: Receiving legal advice alone isn’t enough to solve the problem that the in-house legal team is dealing with. For example, in a regulatory environment, simply saying, yes, GDPR is coming and here it is, and here’s an 80 page memo on GDPR. That gets handed off from a law firm at a very high price point to an in-house legal team. The in-house legal team then has to figure out, what does this mean for their business, for their corporation, who’s their main and only client?

That disconnect is no longer going to be acceptable going forward as the pressure on the in-house team to move at a faster pace, where they’re not going to have necessarily the time to continue to assess and debate the pure legal concepts, but really, it’s all about applying it to a business goal. It’s the business that needs to accomplish something, and without the help of the business and all of the different skill sets that business brings with them, for the lawyer, it’s going to be very hard to really connect between the great legal advice, expensive legal advice they receive from a law firm, and then the business goal, that they’re there to serve at the company at which they work.

Lucy Basilli: Why are these other professionals necessary? Two reasons. One, other types of skill sets are needed to help the engagement between the law firms and the in-house legal departments be more effective. That’s the how. That is moving away from the “ping-pong” of: I have a question. I’m going to send it to a firm. The firm’s going to answer my question, and they’ll send me a bill. I’m going to pay the bill and then we’re done.

That engagement, that back and forth can only be improved with the help of people who understand how to use smarter, better, collaboration tools, with people who can really dive into that process of engaging each other and help optimize the process to move faster, to move smoother, to access information and data more readily so that you’re not waiting. To acknowledge that you can play a big role, but again, you need people who can bring to light some of these different options, because the attorney’s job is still to deliver that legal advice from the law firm.

Lucy Basilli: They don’t need to be process experts. They don’t need to be green belts in Six Sigma. They don’t need to know how to architect solutions, but they need to know when to bring in all those people who know how to do that other stuff. Let’s just call it “other stuff” for lack of a better word because that’s the only way they will improve and enhance the engagement experience with the in-house team that’s moving at a faster pace than every before, and that pace will only get faster. The pace is never as slow as it is today because it’ll always continue to get faster. That’s one main reason that you need all these other professionals, is the how of the engagement has got to evolve and become more modern, faster, more efficient, more immediate access to information, and immediate access to data and answers.

Lucy Basilli: The other end of the spectrum, why you need these other professionals is really, goes to the core of what is being delivered. That legal advice then needs to be consumed in a business setting. Engaging people who have experience with the running of the business itself, of the company, of the corporation, of that client can really help move that advice from again, a nice piece of legal theory, and accurate legal theory into something actionable. Often times it’s then the lawyers in-house that are finding that they need to engage other professionals, and maybe it’s from their “client group” in the business or maybe there are people within the legal department that have now been brought in who are more closely connected to the business itself.


Chad Main: Let’s move away from the why and talk about a different how. How you get buy-in, either at your law firm, or at your corporate law department. You were at Microsoft for a longtime. You instituted some of these changes there. How did you do it? What was your experience there?

Lucy Basilli: I’m a big fan of small wins along the way. It’s great to get supporters, sponsors and fans along the way. In my case, my experience was that when I could demonstrate a value for that attorney for whose job I’m trying to change, or impact, influence, in a positive way I hope, it’s to work with them in a way that they see that value and then become part of the solution. My specific experience was in contracting. Every company has contracts. Every company has too many. This is a job security for every transactional lawyer. There’s always going to be contracts. How do we, as a company, no matter where you are in-house, how do you do them a little bit faster, a little bit more efficient? How do you take some smart risks?

Lucy Basilli: What I realized is, to the extent of course I had control of that work, it was very easy, because I just had to convince myself. But to the extent that I was working with and collaborating with other attorneys across the department, it was critical to show them the value and the benefits of embracing the change. They weren’t the ones that had to engage with different professionals and incorporate different skill sets into their day job. I was doing that on their behalf. I just needed to get their buy-in. The best way is to show real value. Usually the value for most attorneys is of course, time savings. Everybody’s buried. That’s the first complaint you hear. What we underestimate is the quiet wave of resistance from those attorneys who like being buried. They like having the work they have on their desk. They feel comfortable with it. Changing it by encouraging them to move to more complicated work actually may not be perceived as a value-add.

Lucy Basilli: On the one hand, you’re working to demonstrate the value and get people to come along. On the other hand, you have to really understand and be certain that what you perceive as value is also perceived as value by the person with whom you’re trying to convince. I think that functioning on assumptions or presumptions can be a little bit dangerous. That’s the flip side of that coin. But that’s it. he best answer is get sponsors and believers to come along with you, early on by identifying wins, by demonstrating the change, by demonstrating the value of using these alternative sets of skills that are out there and available.


Chad Main: We’re going to step away from our chat with Lucy for just a few minutes. It’s now time for the segment where we sit down and talk with a legal founder. Today we’re talking to Nehal Madhani, the founder of Alt Legal. If you work in a legal practice that does anything with intellectual property, like with trademarks or patents, Alt Legal just may be an app you want to check out.

Nehal, thanks for being with us today. Tell us a little bit about Alt Legal.

Nehal Madhani: Sure. Alt Legal is cloud-based IP docketing software. For those who aren’t IP lawyers, what we do is we help law firms and in-house legal departments create new IP filings by getting all their information needed for them, automatically create them on government filing websites, and then the worst and most tedious part for any IP lawyer is tracking these deadlines. Our software will automatically connect to government databases, identify their filings and then calculate their filing deadlines for them, so they don’t have to do things manually anymore.

Chad Main: It connects directly to the attorney’s calendars, is that right?

Nehal Madhani: That’s right. It will take all that information, once we calculate these deadlines, we’ll send them alerts automatically by email. We’ll tell them about any changes that happened to their IP filings, and then we’ll take all that information and plug it into their calendars as well. For a lot of IP professionals, whether your in-house or at a law firm, it essentially provides some of the functionality that would traditionally be done by a docketing clerk or IP paralegal. For the docketing clerks and IP paralegals, they don’t have to do input data manually and worry about mistyping a four, when it was supposed to be a three, anything like that. It’s something that’s made possible with data, electronic filings and then smart algorithms.

Chad Main: I know in a prior life you were actually a practicing attorney, but before we started today we were talking a little bit. Come to find out, the inspiration for Alt Legal was not from your practice of law but something else. Can you tell us a little bit about that?

Nehal Madhani: Yeah, absolutely. I started my legal career at Kirkland & Ellis in the New York City office, and having graduated law school in 2009, there weren’t too many other opportunities available, so I started in the restructuring group at Kirkland. I did Chapter 11 reorgs, and in 2009 there was plenty of it to go around. Did that for about five years. I last started building one tech business which was at the time a marketplace connecting lawyers and businesses together so that they could find each other and work together with less friction in that transition.

Along the way I ended up doing my own IP work, and I found that whole process to be so cumbersome, so manual, so rife with errors, that I shutdown the legal marketplace, recruited the IP paralegal to join me, and the two of us started building IP docketing software. It wasn’t something I’d traditionally known about, but once I saw how things were being done it just seemed ripe for automation, and ripe for using data.

Chad Main: I think I saw something too that you actually taught yourself to code. Is the right?

Nehal Madhani: I did. Back in 2013, [the movie] The Social Network had just come out. Everyone with any kind of business mindset thought all they needed was a technical guy or gal and they could just build the next Facebook or any billion dollar business. I wasn’t able to really recruit anyone, so more out of necessity I just said, if I’m going to be building a tech business I have to know the fundamentals. I have to be able to do this myself, so read a lot of online tutorials, and just started building, and probably hit my head on the desk quite a few times. Eventually it all came together.

Chad Main: Kudos to you. That’s great. Tell us, who is Alt Legal for? It looks like it’s for pretty much any IP attorney out there. Is that right?

Nehal Madhani: That’s right. Our customers today range from solos to AmLaw firms from privately held companies to some of the largest publicly traded corporations in the country. We’ve been able to serve all ends of the market, but for us, a lot of our outreach, a lot of our focus is on small organizations just because it’s an easier sales process. But really, any IP attorney that is managing a good number of trademarks would really benefit from our software, make sure that they don’t miss any deadlines, subject themselves to malpractice, or worse, lose the trademark.

Chad Main: Last but not least, tell everybody where they can learn more about Alt Legal.

Nehal Madhani: You can find us at You can engage with our team right there through our live chat. You can also find us on Twitter @AltLegalHQ, and reach me at


Chad Main: Okay. Let’s get back to our conversation with Lucy Basilli.

As noted at the beginning of the podcast, Lucy recently left her position in the legal department of Microsoft and launched InnoLegal Services. To use modern parlance, she pivoted from one position in legal ecosystem to another, from in-house lawyer or consumer legal services to an advisor to legal departments and lawyers in how they should deliver and consume legal services.

Lucy Basilli: It’s a law firm and consultancy. Interestingly enough, the reaction is quite different depending on who I say that to. On the one hand attorneys are immediately perplexed. Well, which one is it? I say, both. Well, how? Very simple. Under the umbrella of a law firm I could provide all the consulting services I want, but the reverse is absolutely not true, number one. Number two, perception. In dealing with attorneys it’s very important that they understand that I am not a recovering lawyer who’s moved from the practice of law into legal operations. Because the minute in an attorney’s mind that shift has happened, I am now outside of the box. I’m in a different bucket. That goes back to my original concept of this whole lawyer, non lawyer. It’s interesting and that is a 100% proven reaction that attorneys go through.

Lucy Basilli: As I was thinking about the work I want to do, which is definitely consulting with law firms and legal departments on how they either deliver or receive legal services, there is an aspect of it where I want to provide what is a traditional kind of legal advisory role, legal advice, especially when it comes to risk. So much of change in the legal ecosystem has to do with attorneys accepting risk, understanding risk, taking risks, being comfortable with risks, and that is a very bright line for most attorneys of whom they’ll entrust to provide them guidance on that. By continuing to be a practicing attorney with a law firm, I can provide legal advice to the extent it enables a better consultancy experience for the client I’m dealing with.

Chad Main: I had to ask Lucy, what was her motivation for leaving the security of a very coveted position in the legal department of one of the world’s largest tech companies for the great unknown of entrepreneurship? She had a great answer. It’s because she’s a unicorn lawyer.

Lucy Basilli: At a metaphysical level it was wow, I’ve been doing this thing for a long time. I’m super comfortable. I love what I do. I love my company. But, is there another calling for me? It was very kind of go through this thing in your career stage in life, on the one hand. On the other hand I was seeing a need in the industry for people like me. I’m going to say it. These freakish lawyers, where I’m going to loving refer to us as unicorns. We’re these mystical lawyer creatures who love the practice of law, love being an attorney, but really appreciate and enjoy the operational aspects. Again, the how of being an attorney. If I’m tasked with handling hundreds or thousands of contracts, as a lawyer, negotiating them, having a team of people who negotiate those, why wouldn’t I want to do it in a more creative, efficient way, where I optimize on process and I use technology, and I think about systems? I think for me that combination of both is what I enjoyed the most in my job. At some point it felt like others needed that same help.


Chad Main: After leaving Microsoft, Lucy actually only spends part of her time on InnoLegal Services. Another reason she left Microsoft is because she wanted to get involved in the excitement and challenges of working for a startup. When she’s not consulting others on legal ops, she serves as Chief Legal Strategist for LawGeex, a legal tech company that helps out with contract review automation.

Lucy Basilli: As part of my metaphysical, or philosophical search for the next career move, I really had those desires to work in the startup environment. I felt like that was an energy that I was missing and really needed to experience in my career, at some point. So, enter LawGeex that was just right up my alley, using the latest artificial intelligence and automating contract review, which is my day job, reviewing contracts and managing a team of humans that did that. It just seemed, what an amazing, logical connection for me. Then, in talking with them, we realized that was the right combination of time and skills was for me to help them at this more higher level, strategic role where I can help influence their marketing strategy, their sales strategy, their product roadmap, help engage with customers. Help really consult with customers too because as we’re noticing, and as you know, I’m sure all the unicorn lawyers know, gotta understand your people and your processes before you start getting into technology. I liked being able to play that role as well, and help provide some best practice and tips to their customer.


Chad Main: As I was preparing for my interview with Lucy I read a bunch of articles she wrote and listened to a couple of other podcasts she did. In one of those podcasts, she discussed her belief that if legal is really going to change, it’s incumbent on younger lawyers to help drive this change. I wanted to ask her about it.

Lucy Basilli: The change that is happening in the legal industry, has got to come from the up and coming future leaders of legal. There are a lot of current leaders who understand that something’s brewing around them, but they’re also quite comfortable. They’re comfortable financially. We see their reports, right? We see the Am Law reports. The incentive to change is certainly not a financial incentive. The only incentive to change right now is really coming from the clients, and to the extent the clients are demanding change. For anybody who’s looking at the future coming their way, the associates, the junior partners are the ones who are going to be carrying this, their firm, their organizations. The demand of change from their clients plus with just the evolution of the legal services market, because of all these other players that I mentioned before, the law firm is going to have to look different.

Lucy Basilli: I am looking to these associates who are also graduating at a time they’re used to instant access to information. They’re used to different work-life balance. They have different career goals than becoming the next big partner in the big corner office. They’re used to of course, technology. It’s in every part of their lives. They get to a law firm, and it just feels like a step back in time still. I really do feel like it’s going to be the future leaders, let’s call them, because I don’t like calling it generational. But it’s really the future leaders of the firms that I think need to show that initiative. It’s hard, but they need to share their ideas. They have them. I just hope they’re not shying away from sharing them.

Chad Main: I don’t want to sound too cynical, but they will receive pushback from other lawyers, other partners, other lawyers at the firm. You and I both practiced in law firms. What is your advice to an associate that has an idea. Hey, let’s improve our process to handle discovery, or handle this transactional matter? What is your advice to them to try to change people’s minds?

Lucy Basilli: My advice is simple. It’s find the partner who’s going to listen. Find the one that when you mention this, don’t roll their eyes, don’t blow you off, don’t ignore you. They’re out there. I promise that at every firm there is somebody like that, and maybe a group of people like that, so you have to find them. Don’t waste your breath trying to convince somebody who isn’t interested. You can tell pretty quickly. They’re out there. You just have to do a little bit of homework and it may not be in your own practice group. It may not be the people you engage with on a daily basis, but once you find somebody like that, turn them into a champion, and pitch something. Pitch an idea. Even better so, and this is a harder one for associates to do, but to the extent they have really good direct client engagement and client contact, talk about it with a client.


Chad Main: If you haven’t figured out by now, Lucy has vast knowledge and experience with legal service delivery, and is more than willing to share it with others. In fact, I’ve got good news for you if you want her to share it with you directly. She’s an instructor at the Institute on Legal Innovation and Technology at Suffolk University Law School. A couple episodes ago I talked to the head of that program at Suffolk, Gabriel Teninbaum, about all the cool stuff they’re doing there. If you want to learn more about this school and the program, I highly recommend you give that interview a listen. Anyways, let’s hear from Lucy about what she’ll be teaching there.

Lucy Basilli: I’m teaching an overview of legal operations. What that means is really dissecting it into … It’s 10 modules and each module addresses one of the key capabilities, or functions that really are all under the umbrella of legal ops. Legal ops is such a big topic and it gets confused where yes, it’s a profession or a career, but really it’s just such a combination of so many different pieces. At every company it looks different, because it depends on what they’re interested in. For example, one module is on spend management. Another module will be on project management. It’s a high level overview of each one. It’s intended really for people who aren’t in legal ops, but hopefully for some of the curious lawyers out there who are wondering, what is all this about, because they’re hearing about it, I’m sure in the legal news.

Chad Main: Well, it sounds like it would be well worth taking the class. Lucy, appreciate your time. If people want to get a hold of you, how do they do so?

Lucy Basilli: The easiest thing is probably to look me up on LinkedIn, or shoot me an email,, or LinkedIn is always great as well.

Chad Main: Well, that’s a wrap. We hope you liked it. If you want to subscribe, you can check us out on pretty much any major podcasting platform such as iTunes, Google Play, Stitcher, iHeartRadio, etcetera, etcetera. If you like us enough, maybe even give us a five star rating. If you want to get ahold of me, you can shoot me an email at That’s Thanks again for listening. We hope you tune in next time. This has been another episode of Technically Legal.

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Episode 10: Zach Abramowitz on Legal Tech Trends & Law Firms as Incubators

For Episode 10, we connected with Zach Abramowitz in Las Vegas during the Corporate Legal Operations Consortium (CLOC) conference. Zach is a lawyer, legal technology writer and entrepreneur. Zach handled mergers and acquisitions before he left the practice of law to launch, a tool that lets users have dynamic, live conversations (similar to a chat) and embed the conversation on a website as it unfolds.  You can check out a cool example from Bloomberg Big Law Business when Zach talked to Mary O’Carroll, head of Legal Operations at Google.

Zach also writes about legal tech for several outlets, including Above the Law. So, we talked to him about trends in legal tech (including the gaining popularity of contract analysis and automation tools) and how lessons learned by e-discovery software companies helped pave the way for other legal tech applications. We also talked to Zach about whether the next generation of legal tech companies may very well be hatched in law firms.

You can find Zach on LinkedIn, on Twitter @zachabramowitz or by email

Legal Tech Founder Segment: Catherine Krow of Digitory Legal

We were also lucky enough to snag an interview with Catherine Krow, also an attorney and the founder of Digitory Legal, a cloud based legal budgeting and resource management platform. Digitory Legal is a great tool to help lawyers and their clients craft realistic and more accurate budgets for their legal matters.

You can learn more about Catherine and Digitory Legal on LinkedIn, Twitter (@cmkrow or @digitorylegal) or by email ( or phone (888-811-7211).

Things We Talk About in This Episode

Max Kellerman

Reply All

Above the Law



Y Combinator

Gravity Stack

Zach’s Article in Bloomberg Big Law Business on Law Firms Developing Software

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

Background Photo Above by Markus Spisk



Chad Main: In this episode of Technically Legal, we sit down with Zach Abramowitz, lawyer, entrepreneur, writer, and generally a guy very dialed into the legal tech world. We also sit down with Catherine Krow. She’s the founder of Digitory Legal, an app that helps lawyers put together realistic budgets. One of the best things about doing this podcast is that I get to meet so many of these smart and interesting people, and every time, I learn something about them totally cool and totally out of left field, like this great nugget I got from Zach.


Zach The Legal Intern at ESPN Radio

Zach Abramowitz: I worked at ESPN Radio when I was in law school. I used to go every day to Madison Square Garden, and I worked on the Max Kellerman Show. At the time, I really just wanted to get into sports. I went to law school wanting to become the next Billy Beane, the next GM. I looked for every opening in sports possible, and I emailed Max Kellerman, and I was like, “Listen, you need a legal intern.” He said, “Why do I need a legal intern?” I’m like, “Well, I’ve heard you a bunch of times on your show, and you’ll talk about some issues in law, and you’ll say, ‘Well, if I had a lawyer here, then we’d know the answer to this, but since I don’t, it’s not really worth talking about. Let’s move on.'” I was like, “I’m going to be that guy. Any time you have some legal issue in sports at all, anything you want researched, I’ll do that legwork, and I can put it together very quickly,” and again, I had no interest in researching legal issues for Max Kellerman, but I just wanted an in somehow, in something that made me stand out. I became Zach the legal intern for about two semesters.


Reply All

Chad Main: I asked Zach to come on the podcast for a bunch of reasons. One of them is that he’s a lawyer. He did M&A work for a New York law firm. Another reason I wanted him on the podcast is because he writes a lot about legal tech, and is in the know about it.


He writes for a bunch of websites, including Above the Law, but another big reason I wanted to get him on the podcast is because Zach is also an entrepreneur. He and a buddy created an app called ReplyAll. You can find it at Using ReplyAll, you can have text-based conversations, and then embed those conversations on a website.

Zach Abramowitz: A good friend of mine and I just used to have these debates, and I said to him, “Wouldn’t it be great if you and I could take these conversations and publish them, and allow the rest of the world to follow along like a fly on the wall?”

He was like, “Wouldn’t it be better if actually interesting people could publish these conversations? We could follow them.”

We built a tool that websites use to host conversations with experts that they publish as dynamic content, so instead of going to the Wall Street Journal and reading an op-ed that’s written by one person, with ReplyAll, you’re reading a back and forth between multiple authors, multiple perspectives, multiple opinions, and you’re getting to see that interaction, and you get to see it unfold in real time as the conversation actually happens.

We’ve taken that tool and the first big site we worked with was Above the Law, but we’ve also worked with Sports Illustrated, and TechCrunch, and Bloomberg, and Huffington Post. That was the reason, our goal at the time. This was in the early Facebook and Twitter years. We felt that conversation online, when it involved everyone, was not as interesting.

A conversation that anyone can get into is not really a conversation. That’s a conference, and I wanted to be able to create these sort of intimate conversations, and the goal was that you’d get Warren Buffet and Bill Gates having an exchange about strategic charity or giving. That was the real impetus. The fact that we got into legal was totally an accident. I joke all the time. If you had told me that I was leaving law to start a legal tech company, I probably would have never left law in the first place.

I was working at Schulte for two years. I left because I thought I was never going to have any contact with attorneys again, which was part of my goal in starting ReplyAll. What we’ve found so far is there’s so much interesting going on inside of legal right now that we as a company have really honed in and focused on legal, and not just ways to make business in terms of advertising revenue and getting sponsors on our content, but also to help move the conversation forward, if you will, in legal. That’s a lot of the work that we’re doing right now, is helping and getting more involved, very specifically, in legal technology, because I think for the last year, year and a half, I’ve been looking around at all the interesting things going on inside of legal tech and thinking, “Listen. I’ve got the startup skills. I’ve got a really good network in legal.

I’ve been meeting more and more GCs, more and more startups. I know the scene very well. What more can we do here that’s not specifically advertising related? How else can we help companies in this space?” I think that’s what we’re focusing on right now, and I think in that respect, we’ve become very, very obsessed with legal, and other ways to sort of monetize an online asset, which is really what we’re doing.

We’re a publisher. We are just not completely dependent on advertising revenue for our business model. I think that ultimately, we are going to go back. We’ve been pitching deals to big Fortune 500 companies on being sponsors. We were very close to a deal with Sports Illustrated earlier this year, and then Sports Illustrated got acquired, so we’re having to wait out that acquisition, but we’re not specifically a legal tech company. We’ve very much accidentally become a company that is very involved in legal technology.


The Next Big Thing In Legal Tech

Chad Main: Because Zach has his finger on the pulse of legal tech, and talks to a lot of people in the industry, I asked him what seems to be the next type of legal tech that’s gaining some traction and notoriety. He mentioned two companies, Kira and Doxly, two companies that have developed software to analyze and automate contractual workflows. As a side note, I was lucky enough to talk to Haley Altman, the founder of Doxly, in episode six.

Zach Abramowitz: First of all, the idea of legal tech … Legal tech’s been around for a long time. No law firm could exist without SAP, Oracle, IBM, one of these huge companies coming in and building systems for them that could allow them to be a 1,500 attorney firm with offices all around the world. That does not exist without technology.

What’s changed in the last four years, since you and I have gotten into the space, I think what’s changed more than anything is that the technology that’s being built now doesn’t, let’s say prima facie, support the growth and scalability of a law firm. What it seems to say is, “Hey, listen. You don’t need lawyers for that anymore. Now we have an automated solution.” I think that’s been very threatening to attorneys over the last few years, since I’ve started writing about it anyway.

The whole question of, “Are robots here to take our jobs?” I don’t think robots are here to take our jobs, but any time there’s change, there’s uncertainty, and just because industrialization in the past has led to more business and more jobs doesn’t mean it’ll do that in the future. I think that’s my starting place for legal technology right now. The example that I give, I love two companies. Kira Systems was the first technology company I ever wrote about, and the reason I wrote about them was this is exactly what I did in the law firm. I remember talking with other lawyers and saying, “Why do we have people on this? Why can’t this be done by a monkey?” But if I had been as smart as Noah, I would have said, “Why can’t this be done by software?” Noah, that was his concept.

What Kira was doing in those days, when it was Due Diligence Engine, was reviewing an agreement, pulling out a clause, and populating a diligence memo, the templates in a diligence memo.

This was the work that I did at law firms, and I was like, “Holy cow. This is being totally automated right now. Isn’t that something?”

The other company I like to use as an example is Doxly. If you think about what Doxly does, it’s like every deal, I used to say, has two junior attorneys, a monkey and an associate. Monkey reviews documents, just reviews, reviews, reviews, reviews, but there was also an associate in every deal who was the deal babysitter.

They were the ones making sure that, “Okay, what agreements, what papers do we need as a result of our diligence? What do we need to paper this agreement so that we’re covered on all bases?”

There’s a lot of paper that comes in. There’s a lot of signatures that comes in. Consent agreements, all kinds of stuff. Who knows? Every single corporate transaction has to be papered to death, and making sure that all those agreements come in, what we used to do is, we would create a Microsoft Word checklist, which we would continue to version up and send around as new things came up, and it updated. We would check it off automatically, and every once in a while, the partner would say, “Send around the updated checklist.” This is how we really did these deals, and the agreements came in manually, and we populated them, we printed them out, we put them in folders in the closing room. This was a substantial amount of work.

This required a junior associate on every deal who was solely responsible for this. You might have an associate who was doing that who wasn’t actually doing any of the review work. All they were doing was let’s say drafting and deal babysitting. Doxly does that. Doxly’s a smart checklist, and instead of having this archaic process that’s fragmented, it’s streamlined in one place. It’s very simple. It’s very easy to use. It really negates the need to have a full-time junior associate on these deals.

The reason I mention Doxly, I mention Kira going to the trends conversation is both of those are jobs that I did manually that are now being done better with the help of software, and you might even say makes the 2012 version of me totally irrelevant on a law firm deal.


Silicon Valley is Noticing Legal Tech

Chad Main: Contract analysis and automation might be the next type of legal tech software gaining traction, but there are some other great apps bubbling up out there in Silicon Valley, as Zach points out, is starting to notice.

Zach Abramowitz: I like just about any company that comes out of Y Combinator. Two of the most important people who you’ll never hear mentioned are Jon and Carolynn Levy, a husband-wife tandem that are partners at Y Combinator. They were Wilson Sonsini attorneys who have basically hand-picked all the legal tech companies that you know about. ROSS Intel, YC. Casetext, YC. Ironclad, SimpleLegal. Lawyaw just came out of them. They’re a new company. Cognition IP, Atrium, Justin Kan, the founder of Twitch’s company. I’m leaving out some. They have funded a lot of really good companies.


Legal Tech Founder Segment: Catherine Krow of Digitory Legal

Chad Main: We’re going to step away from our talk with Zach for a few minutes, because now it’s time in the podcast for our legal tech founders segment. This is a time where we sit down and talk to a legal tech founder about the apps they’re developing.

This week we talked to a person so nice, she did this interview twice because we ran into some technical difficulties. We talked to Catherine Krow, the founder of Digitory Legal, another one of these apps that I wish would have been around when I was still practicing.

Digitory Legal permits lawyers to put together realistic budgets for their clients and pulls from real world data. It also permits clients to put together real world budgets for their lawyers. All right, Catherine. Thanks for being here today. Tell us a little bit about Digitory.

Catherine Krow: Digitory Legal is a cost management and analytics platform for law firms and clients that was built to help them succeed in the modern legal market. What I mean by that is a market that is moving more and more to alternative fee arrangements and budget based pricing, even for the most complex matters.

Chad Main: Tell me specifically, what does it do?

Catherine Krow: What Digitory Legal does is deliver a deep understanding of cost, how customers focus on resource management, and provides really clear communications, both internally and externally, around expectations. Internally, it can be used to understand costs at a task and time keeper level, set price benchmarks, create accurate budgets and well scoped alternative fee arrangements, and manage to those numbers, and it can also be used collaboratively, with law firms providing budgets, bids, and forecasts to clients through the platform.

Chad Main: You were formerly in legal practice, correct?

Catherine Krow: I practiced law for 17 years, and was a partner at Orrick Herrington for many of those.

Chad Main: What was the inspiration to create Digitory Legal and leave the practice?

Catherine Krow: A few years ago, while I was practicing law, I came to the realization that the legal profession really needed to evolve, and what was happening was law departments were and still are under enormous pressure to do more with less, and you could see that pressure in the meteoric rise of legal operations and legal procurement.

These are job descriptions that barely existed a few years ago, and now are some of the most powerful forces for change in the legal industry. What was happening is an unprecedented level of business discipline has started to be applied to the legal industry, and if you’re going to succeed in this market, I realized that law firms were going to need to examine their processes, adopt new technology, and make some significant changes to really better meet the business needs of their clients.

That was the inspiration, and it was a moment for me, a decision point where I could try something new and try to solve these business challenges in ways that would bring lawyers and clients together, or continue doing the same thing. I decided to take the leap and focus on the business of law instead of the practice of law.

Chad Main: That’s great. Who’s Digitory best suited for?

Catherine Krow: Our target market is the Global 2000 and the law firms that work with them. We focus on the Global 2000 because I feel like the movement to alternative fees for complex matters is being driven by some of these companies, and the need to respond by the law firms that work with them is very, very powerful. It can be used by anyone doing complex legal work, but we are focused on that target market.

Chad Main: Where can people find you and learn more about the product if they want to?

Catherine Krow: You’re welcome to visit us on the web at, and on Twitter at @digitorylegal, or follow me personally @cmkrow, and you can also reach out to us at


E-Discovery Companies Paved the Way for  Legal Technology Companies

Chad Main: Let’s get back to our talk with Zach Abramowitz. Before we left, Zach was talking about trends in legal tech, and how players in Silicon Valley like Y Combinator are starting to take notice of legal technology companies. But Zach also points out something interesting, that newer legal tech companies might have e-discovery companies to thank for paving the way.

Zach Abramowitz: E-discovery, it’s true, it’s becoming a more mature space, but a lot of the people that you see now at legal tech companies, or at some of the alternative legal service providers are veterans of e-discovery.

Relativity Ventures is investing in startups. I think a lot of the players that you’ve seen come from e-discovery, they learned how to build technology and market it to law firms, and sell it to law firms, and work with law firms, and their model is not necessarily the same model that companies in the finance world use. It’s specific.

They learned how to sell into the legal industry. They learned how to design software for the legal industry, and I think they’ve now paved the way for other technology to come in. Again, e-discovery wasn’t necessarily the place you would have thought legal tech got started, but I think if you look hard, you see that a lot of the roots for legal technology are in e-discovery, even if the company is not doing anything related in e-discovery.


Is Legal Tech a Tough Sell to Venture Capital?

Chad Main: Despite all the advancement in legal tech, and all the new great tools that are being developed, and despite the fact that Silicon Valley players like Y Combinator are now starting to take notice, to many VCs, legal tech still may be a hard sell because, as Zach aptly points out, legal tech companies are not rocket ships like a Google, like a Facebook, like an Uber.

Zach Abramowitz: In order to get the investment that it takes to build a technology company, you’ve got to go to VCs. You’ve got to essentially go to Wall Street and tell Wall Street, because again, VCs in Silicon Valley, their boss is Wall Street. Their boss is the Illinois Pension Fund, or T. Rowe Price. That’s who’s investing in VCs, so you’ve got to go and make the case to Wall Street that you’re a billion dollar company, because the VCs, in order to give the 30% return on risky assets to their investors, they’ve got to invest in billion dollar companies.

You can do the numbers anyway you want.It doesn’t work unless a VC builds and hits on a rocket ship. If you think about the original venture capitalists, go back in time, Ferdinand and Isabella funding Columbus, or if you’ve seen The Greatest Showman recently, funding P.T. Barnum. You had to go into huge rocket ship-like ventures in order to make the returns pan out, and most solutions for legal are not billion dollar solutions. Relativity is the outlier. Most great solutions for legal are not going to be billion dollar exits, and because they’re not going to be rocket ships, VCs won’t typically invest in them.

Chad Main: If legal tech is not always an easy sell to venture capital firms, where should people with good ideas look for resources in investment?

Zach Abramowitz: I’ve got a piece up on Bloomberg now, you can go check it out, where I’m going to explain why I think that law firms have the best position, or why they have a very strong position. Before I do that, let’s just acknowledge that this is happening right now. Go downstairs right now. GravityStack, and that’s the company that we’ve worked with, GravityStack is a wholly owned subsidiary of Reed Smith, which is building and licensing technology, and they’ve got products out.

We helped them rebuild … Periscope was the technology they built in-house four years ago, but they’re down there. Orrick is showing off products. Before we get into why this makes sense, let’s just first point out that it’s happening. Luminance is an example. 5% stake of Luminance is held by Slaughter and May, the British law firm, because it was developed out of the firm, so they have a stake in it.

More and more law firms are investing in legal technology, not just in other companies, but in building their own solutions. First point is, it’s happening. Whether or not it’s the best solution, we can now debate, but I think it’s really critical to understand right now that this isn’t some pie in the sky, “Hey, what if law firms developed their own technology?”

No, it’s happening, and I can tell you, I’m talking to law departments that are talking about it too. What makes sense about it? If you’re the law firm, I feel like in some ways you can relate to this, especially from Percipient’s perspective as well, because in some ways, you were sort of like a law firm. You’re not a law firm, but sort of. And by the way, let’s add to that list, Atrium, Justin Kan’s company, Cognition IP was another one, these are essentially tech companies that are masquerading as law firms in order to build the next generation of legal technology. Again, it’s happening now.

Why is the law firm in the best position? The law firm has the best access to the pain points. They know what’s wrong. They know what doesn’t make sense. All they need to do is get in the habit of, “If you see something, say something.” “Hey, we’re doing this in a totally bogus way that’s inefficient to our client and is a terrible process internally. We need to fix this.” They’ve got the access to the pain points.

Second of all, they’ve got the trust of their clients already. You know how hard it was for some of the companies that we’ve mentioned to build a brand and gain trust with law firms and law departments? Axiom has spent 10 years getting into this space and building a brand with clients. It’s not like building trust in other verticals. Building trust with legal, where you’re talking about risk and bet the farm, and screw-ups that could cost the company even more money, building trust is a huge issue in legal, but the law firms already have the trust of their clients.

Third, what law firms have more than anything else is resources. They’ve got money. Maybe it’s tough to get the partners to part with some of that money. That’s definitely an issue, but at a very basic level, they do have resources. If a law firm builds a technology solution, right now I think GravityStack, which is again, Reed Smith’s wholly owned entity, has built a product called Periscope that I believe could easily amount to five to 10 million in annual revenue for them a year. I don’t know about more than that.

We’ll see, but the point is, if I go to a venture capitalist and I say, “We’re five to $10 million in revenue. We can build a company that has five to 10 million in annual revenue,” they’re like, “Good luck with all that. Sounds like a nice lifestyle business,” but the point is, for a VC, five to 10 million in annual revenue is really not anything that gets them excited. But if you’re a law firm, and I’ve come up with a way for you to have five to 10 million more in annual revenue, that’s like hiring three rainmakers who don’t need a corner office, and who won’t lateral.

Chad Main: And if it is truly tech driven, you don’t need the associates and the support staff.

Zach Abramowitz: And you don’t need the associates and the support staff. I think that what you’re seeing, and I’ll give the example before we wrap, I’ll give the example of Periscope and the reason that I think law firms, and again, this goes to the pain point more than the trust and the resources, it was Periscope, this product that Reed Smith and now GravityStack is releasing, was born out of an actual business use case. They were doing their own review, because they’ve got their own internal review team, the Red Team. It’s a $40 million annual business for them, but they were having an issue that reporting on data to their clients took an extraordinary amount of time in terms of inputting into spreadsheets and handling it manually.

It was taking like five days of overtime per month, and they were only able to report on it like once or twice a month, not any way that could be actionable. They would get to the end of the month, and the bill that should have been 40,000 was now 60,000, which they hadn’t caught earlier because they were not reporting on data that frequently. This was requiring partners eating bills. It was something that was causing an issue for them in terms of having their own internal review team, so they built Periscope as essentially to tie into other data sources, pull that information, and allow you to get at the end of every single business day, so that you knew you could budget. You could predict. You could see what was going on inside your review every single day. They knew this was an issue because it was their issue, and for the last four years, they’ve been using this product internally and differentiating their service.

Now they’ve effectively said, “Listen, why don’t we make this available for others to use? If it’s been such a win for us, for our clients, saving 25 to 40% off review, for us, becoming a more efficient and a more profitable group, why are we not giving this to the rest of the industry?”

I think that this is a question you’re going to see a lot of firms asking now, because I think a lot of firms, not only ones that I know about, have built something internally that they then say, like, “Are we the only firm in the world that has this issue? Couldn’t be. It couldn’t be.” Really, really long way of answering. The reason the technology has sucked in legal is that number one, it’s hard to make a business case for the billion dollar rocket ship, and on the other hand, having expensive consultancies develop this software tailor-made is not really a good solution, especially in an era where building Cloud-based technology has never been so inexpensive, so what I think that law firms getting involved may actually fix that.

Chad Main: That’s it for this installment of Technically Legal. We hope you liked it. If you want to learn more about anything we talked about with Zach or Catherine, you can go to the episode page on If you want to subscribe, which we hope you do, you can find us on most major podcast platforms, such as Stitcher, Google, iTunes, et cetera. If you want to get a hold of me, you can email me at That’s Thanks for listening, and hope you’ll tune in next time.

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Episode 9: Gabriel Teninbaum on Legal Tech Education

For Episode 9 we hit the road and headed to Boston to visit Gabriel Teninbaum, Director of the Institute on Legal Innovation and Technology and a legal writing professor at Suffolk University School of Law.

To say that Gabe does a lot of interesting legal tech related stuff would be an understatement. Not only does he head up the legal tech Institute at Suffolk, he also holds positions at Harvard and Yale.

Suffolk’s Legal Innovation and Technology Institute has three main programs: A legal tech concentration for law students, the LIT Lab that pairs law students with legal organizations to do R&D work and an online legal tech certificate program for legal professionals.

And, if holding all his positions in academia was not enough, Gabe’s side hustle is an app he developed called Spaced Repetition that helps law students with their studies and prepare for the bar exam.

Finally, Gabe has a great weekly legal tech newsletter called Lawtomatic.  You can subscribe to that here.


Legal Tech Founder Segment: Rick Merrill of Gavelytics

In this episode, we also talk to Rick Merrill. Rick is a former litigator and the founder of Gavelytics, an AI powered database containing information about judges, their tendencies and rulings.  Gavelytics provides actionable insights that help litigators win more motions, win more cases, and win more business.


Things We Talk About in this Episode

Suffolk’s Institute on Legal Innovation and Technology

Suffolk’s LIT Lab

Legal Lean Sigma

Florida’s Legal Tech CLE Requirement

Ross Guberman’s Legal Writing Pro


IBM Watson Health

Tomorrow’s Lawyers by Richard Suskind

Spaced Repetition

Lionel Hutz Attorney at Law and Owner of “I Can’t Believe it’s a Law Firm” at the Springfield Mall.


Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

Photo Above of Suffolk Law School: Wally Gobe

Episode 7: Atrium’s Augie Rakow & Max Cantor on Technology First Law Firms

For episode 7 we visited the San Francisco office of legal tech start-up Atrium and talked to Augie Rakow and Max Cantor. Augie is one of Atrium’s founders and Max heads up Atrium’s artificial intelligence efforts.

Atrium is actually two companies: Atrium LLP, a law firm focused on providing legal services to start-ups, and Atrium LTS (Legal Technology Services), the company providing operational and technological support to Atrium LLP.

Augie hatched the idea to launch Atrium with Justin Kan, a serial entrepreneur, angel investor and former partner at Y Combinator (a premier Silicon Valley incubator/accelerator that helped launch a few successful businesses like Dropbox, Airbnb and Stripe). Justin’s desire to create a legal tech start-up was at least partly fueled by his experience as a “power user of legal services.”

The talk with Augie and Max is wide ranging: Augie’s studies at divinity school, Max’s hobby of flying planes, why Atrium was founded and how it differs from the conventional law firm model. Augie and Max also discuss the tech Atrium is developing and their future plans.

In this episode we also talk to Jeremiah Kelman of Everchron, a great collaborative case management platform for litigators. If you want to learn more about Everchron, you can contact Jeremiah and his team at


Things we talk about in this Episode:

Nobuyoshi Ashibe the “Laurence Tribe of Japan”

Y Combinator

Article: What Should You Do With Your Crappy Little Services Business?


Episode Highlights:

1:14    How Atrium LLP & LTS is Structured

2:22    Augie Talks About His Experience at Divinity School

4:20    Max Discusses His Hobby – Flying Planes and His Tech Background

8:39    Augie Meets Justin Kan and Starts to Develop the Idea for Atrium

10:45  Interview With Jeremiah Kelman of Everchron

15:23   How Atrium Raised Money From Tech Investors

18:33   Augie Discusses Why it is Hard for Law Firms to Attract Professional Talent

19:54   Max Discusses the Atrium LTS Legal Tech Platform

21:47   Augie Learns Business Concepts from Atrium LTS

24:29   The Legal Products and Areas of Law on Which Atrium is Focused

25:35   Atrium’s Subscription Based Pricing Model

27:05   Max Discusses the Future of Atrium LTS Technology Development


Episode Credits:

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI


Episode Transcript:

Chad Main: I’m Chad Main, and this is Technically Legal. A podcast about the intersection of technology and the practice of law. In this episode, I talk to Augie Rakow, and Max Cantor of Atrium LLP and Atrium LTS respectively.

We just heard from Augie. The Justin he’s referring to is Justin Kan, a silicon valley angel investor and serial entrepreneur. Augie founded Atrium with Justin, and Max was recently hired to head up Atrium’s artificial intelligence efforts. As you’ll hear, Atrium’s working on some pretty cool stuff and just might be on their way to building the law firm of the future.

Chad Main: Before we get to my talk with Augie and Max, some background on how Atrium is structured is important. Atrium is two business entities. Atrium LLP is a law firm, and Atrium LTS is a separate corporation.

Atrium is two companies for a couple reasons. One is for the sake of process efficiency, which is very important to the Atrium crew, but just as important to them and another reason that Atrium is two companies, is that because it is also designed to comply with the regulatory framework that governs law firms. Which, I might add, is not without detractors, and is a whole other topic for another podcast.

In short Atrium LLP provides legal services like any other law firm, but it utilizes the services of Atrium LTS for operational and technical support.

Before we get to the nitty gritty about what Atrium is up to, if you need any evidence that they’re coming at law from a different angle, you only need to talk to Augie and Max for about five minutes to figure that out. Before Augie helped launch Atrium, he was a patent lawyer and did legal work for startups for about 10 years. Most recently he was at Orrick Herrington, but most interestingly, before he began the practice of law, he went to divinity school.


Augie Goes to Divinity School

Augie Rakow: Yeah, so coming out of college, I ended up going to divinity school. Actually divinity school has a couple different tracks. There’s a professional track where you’re really going to become a preacher. That’s really what people think of with divinity school. You think of MLK having a Mdiv and stuff like that, that’s that track.

Also within divinity school there’s a religious studies cohort, I was in that group. I had always really been very interested in pretty rigorous, systematic, discourse about how we live and how society is set up and what’s the good life. Stuff like that.

That’s the connection between divinity and law firm for me. Those are really the two disciplines, where I think the core tools of the discipline consist of making sense of statements about how we should live.

Using fairly abstract concepts that capture human and social values about fairness, if they’re religious, things like mercy and love and forgiveness. If it’s legal stuff it’s things like is a patent obvious? Concepts of whether a patent is obvious or whether it’s a sin to do something, are these concepts that are totally made by humans, and both divinity and law, try to take these concepts and apply them systematically and rigorously, to solve day to day problems. If a couple splits up, who should get the house? To me those are really the commonality between them.

Chad Main: How do you make the jump from intellectual history to law?

Augie Rakow: To law, yeah. I was in a bookstore in Tokyo, I was just browsing through the bookstore, and I came across a law section, and I had had no interaction with law, I didn’t have any lawyers in my family, except a great-grandfather who I didn’t know.

We didn’t have it in undergraduate curriculums at the time, in the US. In Japan and most other countries, it’s a much more widely studied thing at the undergraduate level, and you have sections in bookstores about law and all that. I just picked up a book on constitutional law, written by a Japanese law professor, basically the Lawrence Tribe of Japan writing in Japanese about constitutional law issues in Japan for Japanese law students, and just totally fell in love with it.


Max Takes Flight

Chad Main: Not to be outdone by Augie’s cool story about going to divinity school, Max has a hobby, flies planes.

Max Cantor: So, personal hobbies, I’m also a private pilot. I got my pilot’s license in 2013. It’s always been one of my dreams. It’s tons of fun. That has probably been my greatest exposure to the law. When you start training, you get a three inch thick book on federal aviation regulations. When you say, “What do I have to read?” And the answer comes back, “All of it.”

Chad Main: What do you fly?

Max Cantor: Mostly single engine planes. Diamonds, Cessnas, Cirrus’.

Chad Main: I guess when Atrium blows up, they won’t have to look far to find a pilot to fly the company jet, but in the meantime, Max is responsible for Atrium LTS’ AI efforts.

Max’s background provides some good insight into how Atrium is approaching its legal services. Max is not a lawyer, and before Atrium, had never worked in the legal services industry. He has a computer science background and he himself, is a tech company founder. Coincidentally, he, like Augie, spent some time in Japan.

Max Cantor: Went to school originally for political science and international relations, but just became fascinated with computer science after taking a breadth requirement.

I graduated with a Bachelor’s and Master’s in Computer Science and was offered a job in Tokyo. That’s where Augie and I, like ships in the night, crossed paths, not knowing each other. I was working in Tokyo for few years, notably at Jane Street Capital, running a small trading desk.

Responsibilities as a trader but spending six hours trading, seven hours trading and then another seven or eight hours coding or writing up models and all that and I loved it. After that, I moved to Singapore, where I was running another slightly larger book on another trading desk, and then started feeling the bug of technology more.

This was around 2010, we just had the financial crisis, and some really interesting stuff was happening, so I tried my hand at a startup in Singapore, not entirely successfully. Learned a great object lesson in founder market fit, and that going off and building a consumer loyalty product for a quick service retail, when you have no experience in quick service retail, consumer loyalty or marketing, is probably not the optimal strategy for success.

I moved back to San Francisco and reconnected with a good friend of mine from college, and we launched a startup called DocMunch, whose product was focused on extracting tabular and textual data from PDF’s.

The eventual tie-in to Atrium, years later, was this focus on data extraction and processing semi-structured or unstructured data. DocMunch was acquired by a company called Nitro, that makes an Adobe Acrobat competitor. It’s PDF processing software. I was running a machine learning group at Nitro for about a year and a half before I left to pursue other options.

Actually, Mike my Co-Founder, connected me with Bebe, who was one of the company-founders of Atrium. At the time I wasn’t quite looking for a job. I had some projects going I was really excited about. What sold me, on Atrium, was the combination of what I saw … It was a pretty innovative model. They combine both, really solid legal chops. Orrick was actually our representation for DocMunch, we love them, they’re a great Silcon Valley law firm. Knowing Augie left that to come to Atrium, was a pretty significant signal to me that they were on to something real.

On the other side, they also had Justin Kan, who is pretty much about as far away from a straight laced lawyer, that you can get. He does define himself as a power user of legal services. Much like someone who flies a lot, you can probably spot a lot of things wrong with the Aviation industry, I think he had a lot of insights into law.

The combination of that founding team, their early success, and the opportunities that present themselves, from a machine learning, natural language processing perspective, would you have access to these clients, to these documents, to the legal markup on those documents, was fascinating to me. That was something I just could not say no to.


Augie Meets Justin Kan and the Seeds for Atrium are Planted

Chad Main: As mentioned at the beginning of the podcast, the Justin Max is referring to is Justin Kan, a Silicon Valley serial entrepreneur who’s been involved in several startups, including a live video feed website called Twitch and another called JustinTV, which was a 24/7 live video feed of his life.

Amazon ultimately acquired Twitch. Justin ultimately became a part of Y Combinator, a premiere Silicon valley incubator. Around 2017 Augie and Justin connected. It was at this time, that they started to sow the seeds to what would ultimately become Atrium.

Augie Rakow: I represented Justin’s brother’s company, in a pretty big transaction. I didn’t meet him at that point, we actually met on Facebook, asking his followers how much they pay for their financings and a woman I had hired at Atrium, I’m sorry at Orrick, to help me to stay connected to the community and people like Justin, spotted that and sent me the link.

I didn’t know Justin at the time so I wasn’t connected with him on Facebook. She sent me the link and I responded to his post, saying. “Here’s how you manage the cost and financings. Here are the main two techniques, but that’s just how you do it today. Justin if you’re interested in a more radically new way of doing things, I’d love to talk.”

We met up and talked for four hours, and met up a couple days later and talked for another four hours. Our first three meetings were four and half hours each. We just had so much to share on this. Over the course of the next few months we got to know each other better. It was one of these decisions that sort of happened. The momentum just kind of took over.

Chad Main: You and Justin keep talking and you just decide together, “Hey, I’m going to leave the practice of law, and we’re going to do this.” Is that what happened?

Augie Rakow: Yeah, there were two or three things that really … I came back from that meeting, the first weekend I met him, and I went back to the three biggest rainmakers in my group at Orrick, I said, “Hey I just met this guy, he’s a big deal. I think there’s a 50% chance he launches something that in the next two years will take 30% of our business. That’s my assessment.”

I got different responses. One said, “Oh yeah people have been trying to do this with law firms forever.” Kind of dismissive. “Investors aren’t interested in the kinds of law firms types of profits.” Another one said, “I’m jealous. That sounds cool.” Another one said, “Keep Justin close.”


Founder Segment – Everchron Founder Jeremiah Kelman

Chad Main: We’ll get back to my talk with the Atrium guys in just minute, but now it’s time in the podcast for the segment where I sit down with the Legal Tech founder and talk about their company. Today we’re talking to Jeremiah Kelman of Everchron. That’s a collaborative case management platform for litigators. Pretty cool product. Here’s what Jeremiah had to say about it.

Jeremiah Kelman: Everchron is essentially a collaborative litigation management analysis platform. A software that brings together all the key information on a legal case, and really meant to allow litigators and their team to collaborate effectively. Do analysis, and organize the most important documents in their case.

Chad Main: What’s the motivation? What’s the story behind Everchron? What inspired you to create the product?

Jeremiah Kelman: Sure. Both my company-founder and I were lawyers at firm, Irell & Manella in Los Angeles. We were doing a lot of large scale litigation and that sort of thing.

We were both there for about six or seven years before we left, and founded Everchron. What we were experiencing at the time was just a lot of frustration around working together as a team and being able to organize everything and understand the facts and documents in our cases. Really the way this is done, even today, often it’s just a little crazy and frustrating.

Using essentially Word documents and Excel to organize information. Then a whole host of different systems and tools where everything is all separated out. My company-founder and I, were basically just putting our heads together on what better ways could we bring together newer technologies and software to make the process of litigation a lot easier and more efficient and effective. That was the Genesis of Everchron really, to build a better collaborative way of working with litigation information.

Chad Main: Before the call today, I was checking out the website, it’s got some cool features. Tell us about a few of those.

Jeremiah Kelman: Really what Everchron does, is it gets you a centralized workspace to put together a lot of information today lives in a lit of different places.

For example, you might have all of your case filings and discovery responses and that sort of thing, organized on a file share, or in document management system, and on the other hand you might have a lot of discussion in your emails, you might have some stuff living in Word documents, you might have a whole host of documents in a large e-discovery review database.

Everchron brings in the best of these sources of information, puts it in a central space and then you can do things like, for example, very easily organize your information, your case documents, your key documents, into chronology of key facts and documents.

Our core focus is ease of use. We’ve realized that the idea is to get a whole host of different types of people in here. Could be a senior partner, could be a client, paralegal, so it’s very important to us to make it extremely easy and fast for this collaborating around this information. Very easy to search, very easy to create reports.

The other core functionality of Everchron is our master file, which is the filing system that would keep everything that would be exchanged between the parties, filed with the court. We have a unique filing system that shows relationships of documents to each other.

Finally, really in tune with our philosophy, which is, “A Little In, A Lot Out”, if you’re going to put work into the system, it better give you back a lot. We have automatically generated player profiles, or witness profiles. Just by working in the system, just by putting your documents in here, we automatically give you analysis, and pull together all that different information on a witness by witness basis.

Chad Main: Well cool. I appreciate your time today. It’s a cool product and where can people find you?

Jeremiah Kelman: Sure. You can find us online at or you can reach out to us by email at and we’d be happy to help you get started in learning more about Everchron.


Atrium Attracts Investors Right Out of the Gate

Chad Main: Alright, lets get back to my talk with Augie Rakow and Max Cantor of Atrium. When we left off, Augie had just told us about meeting Justin Kan, and hatching the idea for Atrium. Now the next step was for them to raise money. When the Atrium team went out and raised money, they raised more than 10 million bucks, which is a nice chunk of change for any business, but it’s an especially nice sum for a legal tech business that includes a service based offering as part of its business plan.

As I can tell you from experience, venture capitalists do not get that excited about service based businesses. If you don’t believe me, Google, “What should you do with your crappy little service business”, and check out the first article that comes up.

I asked Augie what was it that they were able to do to get technology investors excited about Atrium?

Augie Rakow: I think the thing that Justin did, at that phase, the kind of thing that he is uniquely talented to do … There’s a lot of stuff where he’s uniquely positioned. He’s well known, he has access to capital-you know access to all that kind of stuff.

What he did that was so unique, I think, was to articulate in extraordinary simple terms, two or three principles that have really broad ranging effects. The two or three principles he came up are really powerful. They’re kinds of things, the more you think about them, the more things start to make sense, and it really pointed a way forward.

I think other people probably would have not hit on those principles; that would be me, or would have made them … I don’t mean to throw myself under the bus here, or would have made them too complex, which also would have been me. They were extraordinarily deep, and they were extraordinarily simple. The value of them was just undeniable.

Chad Main: What are these principles?

Augie Rakow: The most fundamental one, was the insight that explains why so many legal tech startups fail.

It really is an explanation of why law firms don’t buy legal tech. The thing about the billable hour is part of it, I think, but I think the deeper reason is that there is no vehicle to capture …

In a law firm, there’s much less economic incentive to invest in the operations and it’s in addition to the billable hour. There’s an additional factor, and that is there’s no market for your law firm equity.

If you think of McDonald’s investing in developing a new hamburger, that might get more people in the door and you have greater revenue, but it also drives up the value of the McDonald’s stock.

That second part is completely missing in law firms because there’s no market for equity. It leads to all kind of incrementalism and conservatism. It also leads to short-term planning.

Another way to put it is that, I think there are very few people who are in a position to materially influence a law firm’s investment decisions, who are you enough and early enough in their practice to benefit from those investments 10 years out. For contrast, every time I see …

Think of Bill Gates, it’s been years since he was actively involved in Microsoft. He still personally benefits I’d imagine, still personally benefits, every time Microsoft decides to invest in its longer term growth. He personally benefits, right? It drives up the value of the stock, he can take financing against it. He’s beyond needing that, but to this day, he still personally benefits from long-term investments and his kids will continue to benefit, or his foundations will continue to benefit from it. Totally absent in a law firm.


Atrium is Two Companies

Chad Main: Another thing Atrium pointed out to investors when they went out to raise money, was that it’s sometimes hard for law firms to hire high-level non-lawyer talent to support the business. No small part of this difficulty is regulatory.

Specifically, regulations that prevent non-lawyers from having an ownership interest in law firms. By creating LTS as a separate non law firm entity, Atrium is better suited to go out and hire talented developers. Marketers. Business development people, that might otherwise go to bigger name tech companies, rather than a law firm.

Augie Rakow: One of these other principles that I mentioned, that were Justin’s insight into how to fix what’s broken here, is that traditional law firms don’t have very differentiated staffing.

It’s really only been in the last 1- to 20 years that they even started to have marketing teams, and things like that. Our experience is that that’s the specialized professional talent, non-legal professional talent, that law firms attract … Law firms don’t even compete with the Google’s and the Facebook’s and places like that, for that sort of talent.

It’s for obvious reasons that there’s a glass ceiling in most law firms, because of the regulatory rules. They can’t become owners of their law firm. They can take administrative or executive roles within the law firm, but they can’t become owners. This creates a sort of second class citizenship within the law firms. They tend not to be … There’s not the equity upside potential in a law firm. They tend not to attract a lot of the talent.


Atrium’s Tech

Chad Main: As noted earlier, Atrium LTS, the business side, provides operational support to Atrium LLP, the law firm side. However, outside of and beyond operational support, another reason Atrium LTS was founded, was to develop technology that the law firm could use, that his clients could use, and ultimately that other law firms could use.

Max Cantor: Within the technology services, which I’ll assume includes the operation support that Augie mentioned, we have the technology group.

In technology, we have client facing products, which our clients can log on like a portal. They can see certain things. Internal facing products. Those would be tool that for example, our paralegals will use to load up a set of documents from a new client from prior counsel and markup, “This is a counter-party for this contract. This is the effective date for this contract, etc.”

We store that all on our custom document management system. Then we also have another layer behind all that, called the data platform. That’s really where things get interesting. With the data platform, what we’re doing is keeping track of every step in a workflow that our paralegals and attorneys undertake.

When our paralegal needs to markup a document and say this is the counter-party or this is the effective date, those actions are stored. Those actions are stored in a way that our algorithms can be trained against.

What we’re doing, while we’re building these front-end platforms for our paralegals, our attorneys, and our clients, on the backend, we’re training machine learning algorithms to make predictions based on what they’ve seen so far.

In some cases, our paralegals don’t need to manually type in counter-parties anymore. The system will automatically suggest counter-parties. They will suggest effective dates. That’s the approach that I’m trying to take. We’re not trying to replace anyone in the immediate future. We’re just trying to eliminate the manual repetitive tasks that dominate much of legal workflows.


Business People are Key to Atrium

Chad Main: Interestingly, a side effect of having an affiliation with a technology company that was founded by business people, run by business people, and staffed by business people, is that lawyers at Atrium LLP get to learn business concepts that aren’t always normally taught at conventional law firms. Concepts like how to manage subordinates.

Augie Rakow: One of the things I spend the most time thinking about, that I learned from LTS, or get from the LTS side, is really management coaching.Management advice.

I’ve learned a lot from Justin and Bebe in particular, about how to manage a report. It’s new thing for me. I’ve had teams. I’ve led many teams. I’ve sent out invoices to clients where there’s more than 50 … 100 timekeepers listed on the invoice. I’ve been responsible for the work of many people, but I have never been a manger to someone. In a sense of setting their goals, reviewing their goals, being responsible for their career progression, making sure that they … Never done that before.


Fast Growth

Chad Main: Since opening it’s doors in June of 2017, Atrium’s already landed more than 100 clients and they employ a business development team.

Augie Rakow: We just celebrated getting our 100th client. Been in business since June 1. It’s eight months or so. 100 clients or so, actually about 120 to 125 now.

Gotten them through various different ways. A pretty large influx of companies have just reached out to the website when they seen the various press releases.

We also have a fantastic growth team here. We have three or four, five members on the growth team at the moment. Any how you divide it up, they’re all folks that have built businesses or have professional sales careers where they’ve done extraordinarily well, consistent with the ethical rules. The lawyers supervise them. There’s a lot of rules around that, that are very important to follow, but we have a professional sales team, and I think that’s really the difference.

We actually think of the services that we’re providing as products, and so we don’t just do … No law firm would say that they’ll just do anything that comes in the door, but even work that I would have done at my prior firm, we may pass on it. Not because it’s not good work, not good work to do, or not good clients, but we may pass on it because we’re just not providing that service quite yet.

By constraining ourselves, we can streamline our operations and we can be more strategic about how we do try to sell the services that we do sell. It’s that combination of more specifically defining the product. We call it productizing our services and then working with an extraordinarily talented sales team and marketing team to tell the community about those services and guide the sales funnel.


Atrium is Focused on the Startup Community

Chad Main: Like any good Silicon Valley startup, Atrium is laser focused on product market fit. This means, in the near-term, they’re limiting the legal services they offer just to those needed by startup companies. As they refine their processes and grow, they plan to organically move into other areas like M&A and litigation.

However, as Augie points out, that doesn’t mean that Atrium’s structure and MO can’t be applied to non-business related areas of the law.

Augie Rakow: The work we’re doing now, tracks the kind of work that startups get from the leading law firms in this space right now. The Wilson Sosinis, Cooley’s, The Gunderson’s, or a handful of others. Goodwin, Fenwick.

It’s basically that same model. That’s the same menu. There’s already product market fit there, we know that clients consume those services, we know that they’ll pay well for it, and we know there’s talent out there to provide those services. Let’s not screw with something that works.

Over time, we expect to expand. We’ll most likely follow similar growth patterns to the other law firms that have done well in this space. You represent a lot of venture act startups, pretty soon you start selling them to Google. Start selling them Salesforce. Soon it becomes an M&A practice, then you may turn that M&A practice into a buy side M&A practice and gradually expand out from there. We will mostly be a business law firm. I think these principles apply to everybody in our industry.


Innovative Pricing

Chad Main: Not surprisingly, Atrium’s pricing structure’s a little bit different than a conventional law firm. Instead of maximizing billable hours, much of the way Atrium builds clients is subscription based.

Augie Rakow: This market segment of clients really want to use legal, and they want it to be fast, transparent, and price predictable. The fast speaks for itself.

Transparent means they want to know the status of things. They want it to be price predictable. Not necessarily cheap. A lot of times, as long as it’s predictable, they’re willing to pay well for it. Especially if they feel like they’re getting something really good for it.

The subscription really speaks to that price predictability. There’s going to be some variants. A client may need a lawyer’s time for four hours one month, then two hours another month, and ten hours the next month. If you are striving to be unit profitable at the task by task level, then you really do need to track hour by hour, or six minutes by six minutes.

If you only need to be profitable at a client by client level, or at a quarter by quarter level, that gives you a lot more freedom to absorb the variants. We really put that on ourselves to accurately price in aggregate, much like the insurance company might. What’s going to be the likely cost of this? That’s how we absorb the variants on our side.

The clients we’re taking on now … The subscription price varies a little bit. We’re rolling out new pricing in the next couple weeks. Mostly, clients are paying 11500 to 3000 a month.


The Future of Atrium’s Tech

Chad Main: So I closed out this great conversation with Augie and Max with a question to Max about what the future holds to the tech development at Atrium LTS.

Max Cantor: In the short-term future, our goal is to just capture more of the workflows that the LLP attorneys and paralegals are performing. The idea being, that they have to spend less time in Word, less time in Outlook, more time on our systems. That gives them higher value and it’s more holistic.

We can also report back, or give them the ability to generate better metrics. Augie can turn around and say, “This is where our bottlenecks are.” When we’re on a subscription business, in a way we’re arbitrizing that difference and it’s absolutely vital for us to know what we’re spending time on, so that we can then fix that. On the data platform side, our goal is just improving predictions, eliminating more and more tasks.

One of the distinctions that I like to think about, for machine learning, is what I call auto-complete versus Siri. Auto-complete type machine learning tools are tools that have incremental value. If I’m using Google auto-complete, and it’s wrong 75% of the time, I just keep typing. I still get 25% of the value out of that.

If I’m using Siri, and it’s wrong 75% of the time, I get no value out of it, because now I just wasted my time talking to my phone, like someone who might have some issues. Now I gotta go do whatever I was going to do myself. My interest here, has always been to build the auto-complete. To build the auto-complete tools for attorneys.

Not zero touch automation that has to be perfect, but something that helps our attorneys and paralegals 75% of the time, and that is useful 75% of the time. If our engineering team can make tech that makes the attorneys as happy as … Having Augie cover their backs makes them happy, that’s my goal.

Our goal, in a sense, is attorney retention. Make it so much more pleasant to do legal work here, because we have amazing legal tools, that if you go work at another law firm, you lose. If we have that product loyalty to our internal product then that’s a huge win for us.

Chad Main: That’s a wrap for this episode. If you want to learn more about Augie and Max, or find links and more information about anything we talked about, you can check out their page on our website,

If you want to subscribe, you can find us on most major podcasting platforms such as iTunes, Stitcher, and GooglePlay.

If you want to get a hold of me, my email address is That’s

Hope you’ll tune in next time, where I talk to Angie Hickey of Chicago based Levenfeld Pearlstein. She’s the CEO of that firm and she talks about what it’s really like to run a law firm like a business. Until next time, this has been Technically Legal.

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Episode 6: D. Casey Flaherty on Legal Tech Competency, Legal Ops and Client Driven Change

For Episode 6, we sat down with D. Casey Flaherty at the Legal Tech conference in New York City. 

Casey talked about a few things: how many lawyers struggle to master everyday technology, his experience as corporate counsel and the efforts he took in that role to improve the way company lawyers did their jobs. But, a good chunk of the conversation focused on Casey’s belief that inefficiencies in legal service delivery will not change until clients demand change.

Casey is a legal operations consultant and the founder of Procertas, a legal tech assessment and training tool that helps lawyers and their staff master the basic technology tools they use every day such as Word, Excel and the like. 

Prior to launching Procertas and his legal ops consulting practice, Casey was corporate counsel for Kia Motors and got his start as a law firm associate with Holland and Knight.

Casey is also an excellent and prolific writer.  He writes frequently for 3 Geeks and a Law Blog and is the author of “Unless you Ask”  A Guide for Law Departments to Get More from External Relationships.

You can find Casey on Twitter @dcaseyf

In Episode 6, we also talk to Haley Altman, the founder of Doxly.  A legal transaction management platform used by transactional and M&A lawyers to stay organized when they are working on and closing deals.

Find Haley and Doxly on Twitter: @haley_altman@doxlyapp

Episode Credits:

Theme Music: Home Base (Instrumental Version) by TA2MI

Photo above by Seth Schwiet on Unsplash


Podcast Transcript:

Chad Main: I’m Chad Main, and this is Technically Legal, a podcast about the intersection of technology and the practice of law. Each week we’ll talk to a mover and shaker from the legal and technology fields, we’ll learn a little bit about them, what they’ve been up to, and hopefully get a couple real world tips that lawyers can use to integrate technology into their legal practices.

For this episode, I sit down with Casey Flaherty. He’s a legal operations consultant and the founder of Procertas, that’s a technology assessment tool that helps lawyers and their staff master commonly used technology products.

Before Casey started his consulting practice and launched Procertas, he worked in-house in the legal department at Kia Motors. It was there at Kia where Casey got his inspiration to create his technology assessment tool after he figured out that some of the lawyers he hired may not be that great with technology.

But even before that, Casey had figured out that law firms weren’t bastions of technological and business efficiency, because right out of law school he worked as an associate at big law.

Casey Flaherty: Took me about a week maybe, less, to look around this big law firm and say, “This is nuts.” And the, “This is nuts,” there’s cognitive dissonance because the people were amazing. The partners in particular were brilliant and hardworking and clearly provided tremendous value to their clients. But the support system, the apparatus, the way that expertise was leveraged through process and technology seemed fundamentally broken to me. And I couldn’t believe that clients were paying for it. And then I became a client.

Chad Main: After a few years at big law, Casey landed his job at Kia Motors. But based on his experience at the law firm, he had some ideas about how to tweak the way legal work was done for the company. He looked for places to cut out waste out of the way legal work was done and make it more lean. He also wanted to leverage his position as client to influence the way outside counsel for Kia did its work or, as he explains it, he knew what he wasn’t going to pay for.

Casey Flaherty: And I took with me this idea that there were lots of things that I didn’t want to pay for, but I also didn’t want to throw the baby out with the bathwater. I don’t think lawyers are completely fungible. I don’t think that everything lawyers do can be commoditized. I don’t think that they’re going to be placed by robots any time soon.

And so the question became how do you get what’s valuable without the waste? How do you make it more lean, and how do you drive changes and behavior as a client? And so I brought in a lot of concepts from supply-chain management and particular site visits. I would go out to my law firms and watch them work and talked to them about how they could work differently and should work differently on my projects. And then of course I would go back because that kind of approach requires sustained attention.


Casey Develops a Technology Assessment  for Lawyers

Chad Main: One of the things Casey did to create efficiency and drive change into the behavior of Kia’s outside counsel was to develop a technology assessment that he required Kia lawyers to take and pass.

Casey Flaherty: And I got some publicity for that. And the publicity focused on one important, but controversial aspect, and that is that lawyers suck at Word, Excel, and PDF, that they spend most of their time in these core technologies, and they’re not good at using them. And again, not because they’re lazy or stupid, but because they’ve never learned. And people were incredulous when I said that. In particular, relationship partners were incredulous when I said that. And so it wasn’t enough for me to say it, I had to prove it. So I created an assessment, a bunch of tasks that we had paid for that I could complete in 20 minutes. And it took the average lawyer or paralegal over two and a half hours.

Chad Main: Not surprisingly, Casey got some pushback from his attorneys about his technology competence assessment. “We’re lawyers,” they said. “We’re not clerical workers. We’ve got assistants to do this work. These software skills you want us to learn, that’s not real lawyering.”

Casey Flaherty: If it affects quality, speed, cost, or consistency, it’s real enough to me or, more glibly, if it shows up on the bill, it’s real enough. What you’re really saying is that’s not where the lawyers add the most value. On this, we completely agree, which is why it’s so tragic that they waste so much time doing it.

And then you get to the next objection, “Oh, well, that’s what we have secretaries for.” There are a few problems there. Number one, law firms, even the biggest law firms, have been laying off secretaries for years. I collect press releases from law firms where they cite the fact that lawyers are using technology as the reason for their layoffs, that, oh, the lawyers are using technology. But to say that, it’s true, but it doesn’t mean they’re using it well.

Number two, that assumes that the secretaries know what they’re doing. They don’t. I test them. They haven’t had the training either. And this isn’t just about cost, it’s about overall speed, quality, and consistency. And you, as a lawyer, are responsible, 5.1 and 5.3 over work you delegate. It still has to be done competently. And using technology properly is not just about cost. It’s about competence. It’s about getting the right work product out in the right amount of time. And so the delegation dodge, and I’ve written about the delegation dodge, didn’t work with me, still doesn’t, and it’s becoming less and less true over time.


Procertas Legal Consulting is Born

Chad Main: As mentioned at the beginning of the podcast, Casey ultimately left Kia Motors and watched his legal ops consulting practice. He also decided to make his technology assessment tool available to everyone and launch Procertas. If you want to learn more about Procertas, you can go to or just Google Casey Flaherty, and information about it will come up. I’ll also post a link to it in the show notes for Casey’s episode page, and you can check that out at

Casey Flaherty: What I expect my legacy to be in the legal space is integrating basic tech training into our core curriculum. At law schools, in CLE, in law firm training programs, law department training programs, government organizations, I think we need to take seriously the fact that to be proficient with modern technology, you still need to train. And it doesn’t matter how smart you are

Our technology is not intuitive once you get past the basics, and to do what we do, you have to get past the basics. And so that’s one thing we did. I’ve automated the assessment. I’ve also automated the training around it to create a competence-based learning platform. The idea being that you take a test that identifies what you know and what you don’t. Both matter. What you know means that you test out of training you do not need because we don’t want to waste your time. And then what you don’t is probably more important because people don’t know what they don’t know. Then we have to move in to fill their gaps, the now identified gaps in their knowledge. And so I’ve created that competence-based learning platform.

I don’t want to say it’s my passion because, frankly, I get very bored talking about Word. I feel like I’ve gotten all this credit for a statement of the blindingly obvious. And yet persistence matters to perception. You have to repeat over and over for the message to penetrate. And so I’m willing to do that, and so that’s my evangelism.

Chad Main: As you can tell, Casey’s pretty passionate about Procertas and its aim of helping lawyers master the software they use every day. But Casey’s real expertise lies in his legal operations consulting practice. It’s there where he helps law firms and corporate legal departments improve the way they deliver legal services.

Casey Flaherty: What puts food on the table and where I get excited is I also do legal operations consulting because again, the legal tech assessment was small piece of what I was looking at. I think holistically about legal service delivery. So the use of data and analytics, automation, knowledge management, project management, process re-engineering, and that is something I’m really passionate about. And so I do legal operations consulting for large corporations and law firms.

Chad Main: And what type of tasks … Let’s say, multinational corporation hires you. What kind of consulting, what kind of work do you do for them specifically?

Casey Flaherty: Well, I’ve created legal operations departments, so gone in and help them set up an actual legal ops function. Or I’ll take on a very specific task like a convergence initiative.

Chad Main: Convergence is?

Casey Flaherty: Yeah, so let’s say they have 300 law firms, and that’s way too many, it’s an administrative burden. Their spend is too diffused for them to leverage it. They’re not getting any kinds of economies of scale. I will help them winnow down the number of firms they use, and then negotiate the arrangements with those firms and also setup an outside counsel management program.

Chad Main: Based on his experience both as a law firm lawyer and in-house as corporate counsel, Casey has developed a philosophy on which much of his consulting practice is based. As alluded to earlier, Casey’s a firm believer that improvement into the way legal work is done ultimately must be driven by the client. In fact, he believes it’s the responsibility of legal clients to push for this change. And if they don’t, they’re not doing their job.

Casey Flaherty: One of the big questions I have when it comes to external resources is how do we weave continuous improvement into the fabric of the relationship. And a lot of that comes from the clients. Clients are urgency-drivers and in many ways have abdicated their responsibilities to channel captains and have decided not to concern themselves with how work gets done. Just what is the work and how much are we going to pay for it? And you lose a lot of the incentives to change when you abdicate that responsibility. And so I want to reinsert the client into active management of how work gets done.


Clients Must Drive Change in the Legal Industry

Chad Main: So if Casey is right, if it really is a corporate legal client’s responsibility to push for change in the way legal services are delivered, how does he suggest they do this? He says they do by becoming more sophisticated in the way they purchase legal services, and that starts with understanding how supply chains work. However, he is also very quick to point out that just hiring more lawyers and throwing more bodies at the problem is not the answer.

Casey Flaherty: As much as we want to fight it, corporate law departments need to become sophisticated consumers of legal services. And to do that, they really need to understand how supply chains work, how to manage one, and how to put together a true legal value chain. And we haven’t done that. Instead, faced with the more for less conundrum, which in-house departments do face, we’ve been on a two-decade long hiring binge. It’s very simple math. It’s cheaper to bring a lawyer in-house than to pay them through a law firm. But it’s also just labor market arbitrage. You’re now paying the same lawyers to do the same work the same way. And you end up replicating many of the pathologies of law firms. And yes, it’s at a lower cost per capita, but it’s not sustainable. You can’t keep throwing bodies at the problem forever. Not only that, it’s much harder to fire an in-house lawyer than it is to switch law firms.

And so I am at a high level of proponent of insourcing, at least from the perspective of the mid-’90s and later. We needed to achieve a certain amount of scale so that we could have specialization and sophistication within law departments. It’s not that all insourcing is bad, but I think in many respects it’s gone too far. At this point, there are more in-house counsel in the United States than there are in the domestic offices of the Am Law 200. Law departments, one lawyer or more, are responsible for the purchase of 55% of all legal services in the United States. And law departments have grown at seven and half times the rate of law firms since the late ’90s.

Chad Main: When you say you think insourcing has gone too far, do you mean just the sheer numbers or is it issue with the work that’s being done maybe would be better suited for the law firm or some other legal service provider?

Casey Flaherty: So the answer is yes to both. So I think that there are other organizations that should be better suited to it, organizations that specialize in it, organizations that can achieve economies of scale, organization that can focus on that kind of work. But I also just think there are too many bodies, period. What we like to frame as a cost problem in legal, and I have to credit Professor Bill Henderson for this insight, in fact many insights, but what we frame as a cost problem in legal is truly a productivity problem. And we haven’t spent enough time thinking about and working on productivity. Again, how do we leverage expertise through process and technology? Almost everything has been how do we find cheaper labor, but the demand for legal services is going to continue to increase, and by the way, as it should.

Lawyers are very valuable and as the economy becomes more complex, legal insight becomes more important. So lawyers are complexity engineers. You can look up Dan Katz on that one. Some create complexity, the rest of us solve for complexity. And as the world economy grows larger and more intertwined, it becomes more complex. And so legal services become more important, but you can’t just keep adding lawyers forever. There is still this more-for-less conundrum, and that’s not a cost conundrum. It’s a productivity conundrum.


Legal Founder Segment: Haley Altman of Doxly

Chad Main: Let’s hit the pause button for a minute on our talk with Casey. It’s now time for our segment where I sit down a legal tech founder. Today we talked to Haley Altman, she’s the founder at Doxly. That’s a SaaS-based platform that deal lawyers can use to stay organized when they’re working on and closing deals. It’s a great tool for M&A lawyers.

Tell us a little bit about Doxly.

Haley Altman: Well, thank you for having me, Chad. Doxly is a legal transaction management platform. We are looking to help attorneys close deals in an efficient, streamlined process that gives them extra control and visibility into these very key and important transactions.

Chad Main: And what motivated you to create Doxly?

Haley Altman: Yeah. So I’ve been a transactional attorney for over 10 years. I was an attorney at Wilson Sonsini in Palo Alto and at Ice Miller in Indianapolis. And I started a summer clerk, was an associate working with all these different, complicated transactions, and then trying to kind of develop my own business as well. How do you bring on clients, how do you effectively work with them? And as I worked on really kind of generating this new business and managing all the transactions that I was already on, it just really kind of came to light that we all practice in a very similar way. We all use these closing checklists as the roadmap for the transactions, all the items, documents that need to be negotiated and signed, and tasks that need to be completed. And they’re kept in Word documents and Excel checklists. And so what I wanted to do was give attorneys more visibility into what they’re doing, take away some of those administrative challenges, and really help you focus on doing the high-value legal work that I enjoyed doing.

So I just started looking into what technology was out there, what could we do to improve the transaction process. And after spending about a year and a half looking into it, not finding anything that I thought really met the needs of the market, I really wanted to kind of jump in and build company that gave attorneys the ability to practice and do what they love.

Chad Main: Now when you say you wanted to create a tool that helps attorneys practice and do what they love, how specifically does Doxly do that? Does it free up time? Does it help them remind the tasks?

Haley Altman: Yeah, so with Doxly what we’ve really done is take a kind of a fresh look at kind of managing the transaction process, so taking these checklists that are in Word document that have to be constantly updated throughout the transaction process, we wanted to give people greater visibility. So finding ways to get them the information they needed in a way that didn’t require the administrative side of keeping everything up to date. Then on the closing process, we wanted to take all those pieces that are incredibly tedious, yet insanely important: drafting the signature pages, making sure that the blocks look perfect, that you’ve got pages created for every signer. We wanted to do that for you so that you can focus on the key issues that need to be resolved. You know, the signature process is incredibly important. You don’t want to close a deal and be missing a signature page. You don’t want to take too long getting the signature pages out and collected, that the deal doesn’t close on-time. The value that we bring to the transactions is all of the key negotiating that we do.

We advocate for our client, we think of all the different ways that we can help them achieve their position through this transaction. These are usually incredibly important transactions. You’re helping a company get money so that they can hire employees and bring a vision to life, or you’re helping a company that has grown, secure an exit, or add on another piece that they need to kind of continue to grow their business. And these are all very time-sensitive. And so the administrative side of it can be an incredible burden, but it’s critical at the end of a deal to have every document, the exact form of document that’s been approved by the parties with every single signature page, so that when everyone moves forward, they can do so with the confidence and security that everything has been done correctly.

Chad Main: Well, Haley, it’s a cool product. Thanks for your time today, and how can people find you?

Haley Altman: They can go to our website,


Change Starts at the General Counsel’s Office

Chad Main: Okay. Let’s get back to our talk with with Casey. From the first part of the interview, it should be pretty clear that Casey doesn’t believe much is going to change in the way legal work is handled, unless the buying habits of clients change. So I asked Casey if the consumption of legal services has to change, where does this change have to start? He answered very quickly. He said, “At the top, at the general counsel’s office.” He also says it starts with improving the processes behind the legal work and the training of those involved.

Casey Flaherty: I would start in the General Counsel’s office with the people who are in charge of now large groups of lawyers delivering legal services internally and externally, and get them to stop subscribing to the lawyer theory of value, which posits that we solve problems one smart lawyer at a time. And if that one smart lawyer can’t do it, then we add another one. And then we keep adding lawyers until we have enough lawyers to solve the problem. And it’s not just about saying, “Oh, technology will solve it.” Technology’s nice, technology is a piece of the puzzle, but you really need to have an integrated view of people, process, and technology, and the way that you can embed expertise into your systems. We have to stop believing in magic, because everyone says that they’re pro-technology, and, “Oh, we’ll just throw some technology at it.” And then the technology doesn’t perform. And then they blame the technology and decide that, “You know what, we should have bought different technology.”

The best studies we have come out of MIT, suggest for every dollar you’re spending on technology acquisition, you should be spending up to 10 on personnel, process redesign, and training. And we fail to make that investment, and so the technology doesn’t yield what it should. And again, we blame the technology, which doesn’t make us anti-technology. It just makes us think, “Oh, there’s some other technological solution out there.” And we have to banish that thinking. And so we banish the thinking that all I need are more lawyers or more budget for more lawyers or, oh, all we need is some technology. And you have to, again, think holistically about legal service delivery, about your process, about what problems you’re trying to solve, and what the best combination of people, process, and technology is available to you to solve those problems.


How to Get Law Firms to Embrace  Change

Chad Main: Changing internal legal processes is just one piece of the puzzle. The other puzzle pieces are law firms, and it’s no secret that change at law firms moves at a glacial pace, and that’s probably being generous. So what’s it take to get law firm buy-in?

Casey Flaherty: You demand that they change too. And you don’t just say some words. You actually go onsite and understand how they’re delivering legal services. Talk to them about ways that they can change, put together measurable improvement projects, and then you actually measure it. You come back three months later, six months later to see how they’re doing. And you make sure that not only are you continuously improving, but they’re continuously improving. And so you have to extend both the mindset and your attention to your entire supply chain. And I think when you do that, you’re going to find a lot of legal services both internally and externally that can be unbundled, and you’ll start to have a more diversified supply chain where you’re bringing in law companies where you do find technology that’s the right fit. And so you are replacing labor with technology. You’re also replacing labor with process and less expensive labor. And you’re doing this all the time. There is not finish line. There is no perfect end-state because even if you were to get there today, two years from now you’d be two years behind. And so it is a continuous process.

Chad Main: So it’s all good and well to talk about pushing law firms to change. But if you talk to lawyers at law firms, they’ll point out that despite clients complaining about high billing rates and waste in the process, they really aren’t pushing the lawyers to change. What does Casey say about that? He says if you’re in-house at a company and you’re not pushing law firms to do better, you really aren’t doing your job. In fact, Casey wrote a book about it called Unless You Ask. If you’re interested in checking that book out, I’ll put a link to it on the show notes on the episode page on

Casey Flaherty: So you have to stop being vague. Any in-house counsel can say, “I wish my law firms were more efficient and innovative and cost-conscious.” You’re an in-house counsel. You are the purchaser. You can make the do that. It will require effort on your part. It might even require some uncomfortable conversations, and every now and then you might actually have to switch firms. But these, “I wish outside council did X,” … No, no. It is literally your job to make them do X. That doesn’t make me super popular to say it. And I wrote an entire guidebook for the association of corporate counsel entitled Unless You Ask: How to Get More From Your External Relationships. There’s a primer that I wrote for the buying legal council on service delivery reviews, much shorter than the guidebook, that outlines precisely how I would go about it. But it’s a menu, it’s not prescribed. It doesn’t say, “You have to do X.” Figure out what work you’re doing, figure out how it’s being done, figure out how it can be done better. Here’s the current state, there’s the future state, now how do we get from here to there? And if you’re not paying sustained attention and making progress towards that end-state, then you’re not doing your job.

Chad Main: But at the end of the day, Casey admits that the practice of law really is changing. It’s just not changing as fast as the way some people would want it.

Casey Flaherty: I would say it’s slower than most of us who think about it would expect, let alone like. So it’s slow and uneven. You might have a couple of corporate counsels who do something really interesting in one area, let’s say outside counsel management or information government or use of analytics or whatever it is. And then no one else does it.

And so you have all these outliers, and people look at the outliers and they start to tell themselves a story about change based on the outliers, not realizing that it’s not spreading beyond the outliers. And so the diffusion of innovations and legal is not what at least I expected. And from talking to people here at the conference and all the other conferences I go to, I know I’m not alone in that assessment. Anyone who’s been around for more than 10 years would have expected the world to change much more than it has in the last 10 years.

Chad Main: Do you think the pace of change will increase if people like you keep talking about it?

Casey Flaherty: I have no idea. I had coffee with the great Bruce MacEwen last night. Anyone who hasn’t read Tomorrowland, Bruce is so insightful. And Bruce, he lays out different scenarios for the future, all of them really well-drawn, very provocative. And he doesn’t predict. He has this great line about the future might be unknowable, but it isn’t unthinkable, and so let’s think about it, let’s talk about it. And I said to Bruce, that I have a particular view of the future, but I kind of lost any sense of time. I don’t have any strong predictions about how long it will take. And I will be so happy if it happens quickly, but I’m also prepared to be patient and have it be trench warfare and measure progress in inches. It’d be great to capture huge chunks of territory, but even if that doesn’t happen, it doesn’t make change any less worthwhile.

And so I know I didn’t answer your question because I don’t have an answer. Five years ago I would have been very confident. Very confident. I would have put a marker in the ground. And it’s not that I’m afraid to bet. I’d bet my career on change. I’m not just pontificating from some position of security. I work in this space. My family eats based on whether or not I am right to a certain degree. But I don’t have a crystal ball. I don’t know if it’s going to pick up. But I know it’s happening, and I know it’s happening enough to keep me employed.


“Non-Lawyers” Are Very Important Change Agents

Chad Main: Most of the talk on today’s podcast has been focused on change within corporate legal departments or within a law firm. But no small portion of this change, even if it’s to be positive, will involve players without law degrees, people with expertise in technology, business, and project management. It’s also going to take a change in the way lawyers look at these people. They can’t be viewed as, “non-lawyers,” or lesser-thans, but they must be recognized as people important to the process because in fact they are.

Casey Flaherty: Again, I talked about the mindset shift with the supply chain. I think part and parcel with that is the mindset shift around what I call ally professionals, but with the rules we’ll called them non-lawyers. There’s a lot of different expertise that isn’t strictly legal, substantive expertise that can make a valuable contribution to the delivery of legal services. And so I think shifting your mindset about not just what is valued, but who is valued, and getting past our silly cast system where these other experts are treated like second-class citizens. I think that’s a great place to start. Now, that’s not a concrete step in a particular direction where, oh, you’ve installed this system. But I do think as a general mindset shift, it’s very important.

Chad Main: The last thing I talked about with Casey was a quote that I read in an article he had published that day. And by the way, if you don’t read Casey’s stuff, start today. It’s great work. There’s no question that he is one of the best writers out there on the changes to the practice of law and just the legal industry in general. You can find most of his stuff on Three Geeks in the Law Blog. At any rate, the quote I read that day that was so cool was that system amplifies talent.

Casey Flaherty: Well, it goes back to this idea of how do we leverage expertise through process and technology, because the argument I often get is about real lawyering, and that’s where the value is. And it’s essentially talent trumps system. That what’s important is that I’m a really smart lawyer, and what I do is valuable. So it might be true that I’m a little inefficient, but why don’t you just sit back and let me lawyer, let me do what I do because that’s where the value is. And I don’t completely discount that because talent matters and because lawyers do bring true value. But we can only afford so much lawyering. And so to get the maximum out of the lawyering we can afford, we need to situate them in systems that we properly leverage that talent, that we amplify that talent, that we augment that talent, that we have forced multipliers so that we can truly, truly extract full value from talent that is genuinely valuable.

And so I focus a lot on the system side because the talent’s already there. And the talent is in many ways enduring. We had talented lawyers in the ’80s. We have talented lawyers now. Lack of talent isn’t the problem that we’re trying to solve, how to leverage that talent is. And so I’ll often say that good lawyers aren’t scarce, good systems are. And so that’s where we should be focusing our efforts, on building those systems.

Chad Main: Well, that’s today’s episode, hope you enjoyed it. If you want to subscribe, you can check us out on pretty much any major podcast platform like iTunes, Google Play, Stitcher, and SoundCloud. If you want to get ahold of me, please shoot me an email. My email address is, that’s C-M-A-I-N-@-P-E-R-C-I-P-I-E-N-T.CO. Until next time, this has been Technically Legal.

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Episode 4: Dennis Garcia on Automation, Cybersecurity and the Cloud

In this episode we visited Microsoft Assistant General Counsel Dennis Garcia in his Chicago office. Dennis talked about a few things, including what he and others in the Microsoft legal department are doing to automate and streamline legal work (spoiler alert: bots are involved).

Dennis also talks about the benefits of lawyers using cloud computing and common sense tips law firms can take to shore up their cybersecurity.

Dennis closes out the interview discussing lawyers’ use of social media.

Here are links to a couple articles mentioned in this podcast: One on rules of professional conduct and ethical opinions addressing lawyers’ use of cloud computing and an article Dennis wrote on cybersecurity.

You can connect with Dennis on Twitter (@DennisCGarcia) or LinkedIn.

In this episode we also introduce a new segment we are adding to the podcast. Starting with this episode, we will include a short interview with the founder of a legal tech company to help get the word out about new apps and products aimed at making the lives of lawyers easier.

We start with Ryan Alshak, a lawyer and the founder of Ping, automated time keeping for attorneys.


Episode Credits:

Theme Music: Home Base (Instrumental Version) by TA2MI

Photo Above: Microsoft

L.A. Law Theme: Written by Mike Post, Copyright 1986 Polygram Records

Droids: Lucasfilm, Ltd