Microsoft attorneys Dennis Garcia and Jason Barnwell join us on Episode 31 to discuss how legal teams can successfully and productively work remotely. They also discuss how governmental work from home orders may speed up innovation in legal departments and law firms.
Dennis is an Assistant General Counsel at Microsoft and a prior Technically Legal guest. In Episode 4, he talked about Automation, Cybersecurity and the Cloud. Dennis leads a team of lawyers assisting Microsoft’s Enterprise Commercial Sales and Services team, one of the company’s largest commercial businesses.
Jason is also an Assistant General Counsel and heads up Microsoft’s Modern Legal team. In that role, his mandate is to drive industry leading innovation to digitally transform and modernize the Microsoft legal department.
Dennis and Jason explain that companies must invest in the right tools so that their lawyers and employees may successfully work from home. These tools start with good hardware—devices capable of running whatever software the business needs.
Jason points out that with good hardware, remote workers are well positioned for success because most modern software is cloud based and “meets you where you are” permitting work to be done pretty much anywhere with an internet connection.
Dennis and Jason also explain that for successful remote work, the modern legal team needs collaboration tools to communicate and work with team members, productivity software like Word and Excel to create legal documents, remotely accessible data storage and knowledge management tools.
Both Dennis and Jason agree that change is hard, but lawyers, like everyone else, just need to make the jump and try new tools and new ways of working. And… it all starts with a mindset shift.
I’m Chad Main, the founder of legal service provider Percipient and this is Technically Legal, a podcast about legal technology and innovation in the legal industry. In today’s episode, we have two members of the Microsoft Legal Department, Dennis Garcia and Jason Barnwell. The three of us discuss how legal teams can successfully work remotely and how they can also implement improvements and change into the way they do their daily work.
The first of our guests is Dennis Garcia. He’s an Assistant General Counsel at Microsoft and is a repeat offender to the Technically Legal Podcast. We talked to him in episode four and he discussed automation and cybersecurity in the cloud. Currently, Dennis leads the legal support function to one of Microsoft’s largest commercial businesses, the US Enterprise Commercial Sales and Services Teams. In his role, Dennis leads a team of 16 lawyers that help out over 2000 Microsoft employees across the United States. His team provides a variety of legal services and a good chunk of their time is spent on shaping and negotiating contracts with Microsoft’s large enterprise customers.
Our second guest, Jason Barnwell, is also Assistant General Counsel at Microsoft, but he works in Microsoft’s Modern Legal Group. Jason is a first time guest to the podcast. In his role at Microsoft, Jason’s mandate is to drive industry-leading innovation and to digitally transform and modernize Microsoft legal departments and practices. In his role, Jason works with others in the Microsoft Legal Department to foster a culture of innovation and then working with them to get the tools, technology, and process improvements necessary to improve legal service delivery within the company.
I asked Dennis and Jason to come on and talk about changes that were already afoot in the legal world as far as how lawyers do their work with the use of technology and process improvement. But I also wanted to talk about how those changes might be accelerated as a result of the COVID-19 pandemic. As a result of all the stay-at-home orders, lawyers are forced to rethink and change how they work, not the least of which is having to work remotely.
So Dennis, you’re a baseball guy. The lockdown, the work from home, the social distance thing, how are you hanging in there without baseball?
Oh, it’s been tough. I’m a die hard New York Yankees fan. I was born in the New York area, born in the Bronx and it’s been tough the last few weeks. It’s going to be interesting to see if we see baseball at all given the COVID-19 issues. But what I’ve been doing on a daily basis, I’m a huge baseball card fan. When I was a kid, I used to collect baseball cards and I have all these baseball cards. So once a day I tweet out my daily baseball card and it just sort of reminds me of baseball, reminds me of my youth and it’s a way for me to still stay connected with our national pastime.
Yeah, that’s cool. I’m missing baseball. Hopefully it picks up. Jason, I think I saw somewhere that you like science fiction books.
I do. I do.
Any new recommendations since you’ve been sheltered in place?
I have been thoroughly enjoying The Murderbot Diaries series, which sounds probably much more dystopian than it is. And I think the author’s name is Martha Wells, so she’s got four short-ish stories and I think she has a full length novel that’s coming out in the next coming weeks. And so it’s just a really fun kind of world building exercise that radically changes perspective on what it might look like as we start to have artificial intelligence that goes several clicks beyond where we are now. But it’s interesting stuff.
I want to read something that comes from an article you wrote recently for the Legal Evolution website and your most recent article was written before the pandemic really kicked in. Right?
At least here in America. Yeah, because you had this quote here and I really like it and I think it’s pretty poignant. And the timing was good, maybe more so than you knew it at the time. You said, “The legal business landscape has changed in the decades since I left private practice in ways that suggest we are approaching an evolutionary inflection point.” That is the very reason I wanted to bring you two on the podcast because I want to know if you agree with the feeling that I have. This evolutionary inflection point, I think maybe have been sped up in legal for a couple of reasons.
Number one, many lawyers for the first time are now having to work outside of their office, working remotely and figure out how to do that, how to be efficient outside of the office. Maybe using tools they hadn’t used before because they were used to working at the office. And then the other part of this equation too is you’re seeing a lot of people lose their jobs in legal, which means lawyers are going to have to get more efficient in how they’re doing their work because they will have less help. So do the two of you agree that maybe this what’s going on here across the world really, but in America, might speed up this change that Jason kind of wrote about?
I think the answer from my viewpoint is yes. And Chad, I’m a huge fan, a user of Twitter and I saw something on Twitter not too long ago. There was a quote or a question and the question was as follows, “Who led the digital transformation of your company: A, your CEO; B, your CTO; or C, COVID-19?” In some respects, I think COVID-19 is going to have a huge impact to accelerate the digital transformation of in-house legal departments and law firms, quite frankly. And from my viewpoint, and of course I’m biased on this, but there’s lots of benefits about working remotely when you look at the ability to, for law firms and in-house legal departments, they can lower their costs. They don’t need to have space. They don’t need to have large facilities where people are going to the office every day.
I think enabling remote work also helps recruiting potentially great candidates, great legal candidates when you give them the flexibility to go in the office if they want or work remotely. I think it helps with work-life integration, work-life balance, if you will. I know when I’ve worked from home, I try to take periodic breaks and I may go out for a run on the Chicago lakefront just to break up my day, right? But being able to work from home allows me to do that and allows me to focus on my wellness when needed. You don’t need to spend a long time commuting into the office and then you get that time back, whether it’s with your family or to use that time just to do more work.
And I find that when I work from home, quite frankly, and I see this with my teammates as well, they’re working harder and they’re working longer. And I think when you’re working from home, you need to make sure that you’re giving yourself those appropriate breaks, if you will, because if you don’t, you could constantly work. So I think COVID-19 is, obviously a highly unfortunate event, but sort of a compelling event which will serve to help speed acceleration for digital transformation for a lot of legal organizations.
Jason, to you, do you think this is going to make your job easier, make it easier for you to convince lawyers and legal teams to kind of adopt changes to efficiency models in their processes?
The short answer is yes, because choices is being removed, right? So if we go back several months ago, the process of evangelization was often showing up and saying, “Hey, I have something that I think might help you be more effective.” And there’s been an inversion of that paradigm where, because of resource constraints, because of availability constraints, because of all of these new constraints that have been introduced to our system, it’s now people showing up and saying, “How can you help me get my work done more effectively given these new constraints that I’m under?” And I think it’s going to change the velocity. Right? So I guess we would call that acceleration. Because if you think about the diffusion of technology into how legal work has happened, it has happened. It’s just the rate has been kind of slow, but once it gets in, it usually doesn’t leave.
So I remember when I started my practice, I would still see partners’ secretaries printing out their emails and putting them into an inbox tray on their desks. And now it’s really hard to imagine a world where if you are a modern practitioner where you’re not probably living in some type of email or maybe even a team’s experience, and once people see how these experiences can make them more effective, they typically don’t go back the other way. Right? I mean, I think Dennis is right that technology also has some risks in as much as it can find us anywhere, but it seems unlikely that people are going to be giving up their smartphones anytime soon and once they see how some of the capabilities that come along with a more modern practice can actually make their lives and their work better and help them serve their clients and customers more effectively, I think they’ll be hesitant to give them up.
I agree. I agree 100% and going back to you, Dennis, you talked about the value of remote work. For those who are just now maybe grappling with it in earnest for the first time, you’ve got some experience with it. You mentioned that your team, including yourself, spends part-time at the office, a lot of it remote. What makes it work? From a company standpoint, what is going to make remote work productive for the company and what are the steps they need to do to make sure that happens?
Well, I mean, I think a few things. I mean, I think number one is you need to have the commitment and investment by your company, your firm to invest in leading technology to enable that remote work, right? And hopefully they’re also investing in technology, which is a highly secure, which is focused on compliance and is focused on transparency and privacy, those key fundamental sort of pillars in trust. You want to make sure that you’re working with a highly trustworthy solutions’ provider, right? But hopefully your company is giving you the right technology and the right technology which allows you to operate in a highly secure fashion. That’s absolutely right and important.
I think you also need to make sure that your company provides you with the right training, if you will, to how to use these assets, and I think you need to have the right senior leaders who are encouraging folks to use these assets to role model their usage of assets. They have to actually use it for their teammates to also be willing to adopt it and to use it. I think from a remote perspective too, and I’ve seen this more and more in my role, this is the second year of being in this role where I’ve been leading a large team and of course I’ve learned a lot. And when you have remote folks, you also need to make sure that you’re engaging in what we’d like to call a Microsoft proximity with them. How do you stay really well connected with them?
I know earlier this year before COVID-19 hit, I traveled a fair amount to visit my teammates in various different cities to check in with them, to spend some time with them, to take them out to dinner or to understand, “Hey, what’s going on? How can we help you? How are your business clients?” And still making sure you had that FaceTime even though we’re all working remotely. Of course, I can’t do that now because of COVID-19, right? I can’t travel to see folks in person. But what I’ve been trying to do more and more is to check in with folks on my team on a more regular basis to see how are they doing, how can I help? And doing that periodically. And I think doing that goes a long way to build a little more inclusivity in your team and trust in your team.
So those are some things which I think you need to be focused on and to invest in. I think you also need to create a culture. Even if you’re a remote basis, how do you still collaborate and share information out? And of course, Jason and I are very biased because we use terrific Microsoft cloud solutions, especially in Microsoft Teams, which I use, we all use as Microsoft lawyers and legal professionals every day as sort of the backbone of our practice. And Teams really enables us in an easy fashion to share content to each other and to create teams based upon subject matter areas or maybe your organization and you can create various channels on Teams. And this is how we interact using Teams, not just with Microsoft lawyers who are based all over the world but also with our business clients and Teams allows us to collaborate and to connect with each other in a very seamless fashion. I can instant message my teammates anywhere in the world to see how are they doing or can I get their quick thoughts on a particular matter.
And so, there’s a lot of great aspects of course about Teams. I’m not trying to use this forum as a way to sell Teams if you will, but there’s a lot of technology out there which you could use to really stay in touch with people, to collaborate and connect. But at the end of the day you need to use this technology too, right? And I’ve seen this with a lot of our customers, they’ve made significant investments in technology and that’s terrific and everything, but they still need to use it and deploy it so that it has a really good positive impact on their legal practice.
This is a question for Jason. Speaking of tools and making sure your team uses the tools, I think I read in one of the interviews with you, Jason, that one of the toughest parts of your job was convincing lawyers to adopt change, to adopt tech, to consider innovation. So to Dennis’s point, what are some suggestions if you’ve got people that don’t want to use the tools that are afforded to them, what can you do to encourage them to do so?
Dennis already gave us one of the most effective tools that is available to get people to embrace the tools and experiences that are available. So when our President and Chief Legal Officer, Brad Smith, when our General Counsel, Dev Stahlkopf, help people see how they are using our tools, when they start actually driving their interactions through those tools, that modeling is so, so powerful. When they basically say, “Look, when we’re going to engage, you’re going to meet me here in the productivity stack that we make.” That social modeling, that social proof is really powerful. And then when they set expectations that, “Hey, I would like to see you demonstrate how you are being more effective using what we make,” that’s really powerful and effective too.
And so getting that tone from the top right accelerates everything that follows and then to really get people going, it’s important to help them feel supported in that transformation, in that change. So many of the people who do work as legal professionals, they are experts in a specific domain, but they haven’t always systematically invested in their productivity skills and in using the tools that are already available to them. And so it can be very daunting for these people to get this message that’s like, “Hey, you really need to dig in on this because this is going to make you more effective.” And it feels like there’s a big gap between where they are and where we’re trying to get them.
And so finding the people in your organization who can help bring along your people is really helpful. One of the biggest challenges that I see is legal professionals don’t like being wrong. They really do not like demonstrating that, “I don’t know something.” I think it’s almost like they’re allergic to saying like, “I don’t know how to do this.” Right? And so it’s really important from a cultural standpoint to normalize, “Hey, we’re all on this journey together.” There’s no shame in not knowing how to do a thing. Let me help you. But this is where it gets a little bit tricky. If you really want to catalyze that change, what you don’t want is the people who are supporting your larger organization having to do that one-on-one. Everybody loves that white glove treatment. Everybody loves to feel cared for, but the resources that your organization likely has to bring people along are limited.
And so one of the things that we have done is we’ve used Teams and we’ve created an internal a team called Sealer Productivity Hackers. And that’s where we’ve started creating a shared learning experience where anybody can ask any question about any of the productivity tools we have. And over the last several weeks we’ve been having daily trainings and they’re just quick hits. They’re usually 15 minutes on like, “Hey, here’s how you send a really effective message in Teams.” And what we’re doing is giving people these kind of snackable bites that really help bring them along. But what we’re doing is we’re doing it in the shared space where people can ask questions. What it does is it normalizes the learning experience. And I also note what we’re putting out is not slickly produced. It’s rough and ready. It is often the case that people will ask a question, will be like, “Hmm, that’s a great question. We don’t know, we’ll go look into it, but not really sure how to do that.”
And so we’re trying to normalize the idea that none of us are experts. We’re all on the journey together and we’re seeing some really good results from that. And ultimately what we will do is we’ll take this baseline productivity upskilling and we’ll start flipping that into the next level. Where that goes is what we call citizen developers. Now, not everybody in the organization is going to be a citizen developer, but with the no code solutions that are starting to become available, you can do some very powerful things without having to be a software engineer.
And so what we’re doing now is we’re identifying some of the people who seem to have that proclivity and those capabilities, and so then we’re going to start systematically investing in them so that we can create more leverage on their capabilities because ultimately our scarcest resource is human attention. So anything we can do to get more output on that fixed capacity that we have is just goodness for our entire organization.
I asked Dennis and Jason what companies need to provide employees to make sure they’re able to successfully and productively work remotely. And they both had a few ideas. First you need good hardware. That is a computer that’s up for the task of running the software that the business needs, which lead to the second thing remote workers need, good software to get the job done. Here’s where Jason makes a good point. A good chunk of modern software is in the cloud nowadays. So what that means is the software, quote unquote meets you where you are. So, as long as you have a device cable of running the program, you can work from pretty much anywhere.
So what is that software? Well, for the modern legal team, the software needed for successful remote work are collaboration tools to communicate and work effectively with other team members, tools like Word and Excel to create documents using legal matters. You also need remotely accessible data storage tools to store all those documents created. And if you really want to run an effective legal team remotely or otherwise, you should also implement knowledge management tools.
I think one maybe sort of straightforward and simple thing when you think about it, is if you’re going to work from home, you need to make sure you’ve got the right sort of physical device if you will. Right? And you’ve got to be thoughtful as to what device do you have? I use of course our Surface Laptop. I love this device. I’ve been using it now for almost a year. This is the one real device I’m using every day to enable me to really work from anywhere. To work from home, to work in the office, to work on a plane. It’s my one sort of hardware platform. I know other folks in their home office will have sort of big screens or monitors in their home office. I don’t have that. I really just use my Surface Laptop. I try to keep it pretty straightforward and easy. But I think first thing is to figure out what sort of piece of hardware do you have so that you could take advantage of all these solutions.
And Jason, what do you think legal teams should have at their disposal to really get the job done no matter where they are in the office or working at home or at the coffee shop here in a few weeks?
Well, I think Dennis is right that starting off with good hardware is important. So we’re very fortunate that we work on the Microsoft stack. And so, of course, I’m a total homer and those are the things I’m going to talk about. So the great thing about our stack is it is Mobile First, Cloud First. As long as your hardware is adequate, it almost doesn’t matter what you’re using because the experiences that we are producing, they work great on PCs, they work great on Macs, they work great on iOS, they work great on Android. And so they really do meet you where you are. So a lot of what I think about from a collaboration standpoint is not just the experiences, but what are the systems that you need to link together to be more effective?
So there’s a bit of a maturity model that, if we want to get nerdy for a second, that I often see and it really moves up from starting with individual work and then moving into collaborative work and then work moving into group work and so forth and so on. And so when you’re thinking about the tools that support you when you’re doing individual work that often looks like good old fashioned Outlook and Word, right? But when it’s time to start collaborating, there’s a whole bunch of elements of the Microsoft 365 stack that start to become really, really helpful. So Dennis has been talking about Teams and one of the things that’s really powerful with Teams is it gives you that collaboration canvas, but under the hood it brings together a whole bunch of elements that are really powerful.
So when you create a team under the hood, you’re getting SharePoint file storage. So you’re getting all the goodness that comes along with SharePoint, but you don’t really have to know how it works. It’s just kind of there and it does its thing and it’s all good. The other thing that happens under the hood is it uses the group structure that powers the organizational kind of model that creates permissions. And honestly, the beautiful thing is, again, you don’t have to care. It just does all the security and trust model things that Dennis was talking about in a way that’s secure and transparent, but you don’t really have to futz around with it.
But what’s becoming interesting with us is as people start mastering these elements of collaboration, they start seeing patterns, right? So when you and I do the same work in the same place, we start to see like, “You and I are doing this kind of the same way and that’s a really good thing.” And then we start observing, “We’re getting asked the same questions again and again by our clients. Maybe there’s a better way.” And so that’s when you start moving into some of the other elements of the stack that can be really powerful and start getting you into very, very easy self-service and even some light automation scenarios.
Knowledge management, which you’re kind of talking about knowledge management type aspects there, right?
Look, you said it. All right, let’s go.
There we go.
Yeah. So no, but we’re going to keep it easy breezy. So anybody who is a Microsoft 365 customer, if they go into the web experience, they’ve likely seen, what we call the waffle in the upper left-hand corner. And maybe you’ve clicked on it, maybe you haven’t. And when you click on that, you see that there is a formidable array of things available to you. And I just want to flag a few that people might want to go take a look at.
So one is Forms. So Forms is an easy way to capture structured data. If you can create a very, very basic Excel Spreadsheet, you can create a form. The really cool thing about Forms is it lets you collect data from really anybody inside or outside your organization. And then you start to have this structured view on that information. And so imagine that you wanted to, I don’t know, let’s keep it really simple. Imagine you’re going to have a cookout back when we were allowed to be in each other’s space and you wanted to figure out like, “Okay, who wants to bring what?” If you wanted to solicit recommendations of like, “Hey, I can bring this or that,” you could actually run that through a form. And so that can then bring all your data back to one place rather than maybe the old way of, “Hey, email me your thing that you want to bring and I’ll collate it.” So now that all happens automatically.
But then you can get even more powerful, because what you can do is you can use tools like power automate to take the data from Forms into a SharePoint list. And now you’ve got your data in this shared place that you can do all kinds of other things on top of that. So you could run reports on it using Power BI. You could automatically fire off emails or other notices like, “Hey, we already got something on this and nobody needs to bring that.”
So there’s this whole array of very powerful tools that most of our customers have already purchased, but they may not know is there. And so as they start moving down that path from, we figured out our individual work, we started to make the group work better. Now we’re looking to figure out how we accelerate ourselves and make the most of the limited resources we have. I would really encourage people to go click on the waffle, see what’s there and start poking around and see is there something that can help me get the most from, again, my most limited resource, which is probably human attention.
Jason just did a terrific job, sort of a masterful job, sort of laying out other key workloads for Office 365. And I know that myself and my team, we’re starting to use these additional workloads. So much of what we do as lawyers in the field is we’re working on big contracts with our key customers and we’re trying to do a better job sharing the knowledge and the learnings associated with those deals after we close these deals. And we’ve been here for a long time, we had sort of a standard template we would fill out in a Word Document to capture some of our learnings. And now we’re capturing some of our learnings through Microsoft Forms where we’re just asking two or three straightforward questions regarding some of the learnings from those deals.
And by capturing this information in Forms, it’s sort of an easier sort of experience in capturing that data, a lighter touch for our lawyers to input that data, and we’re getting a wealth amount of data from our folks because they’re submitting this information more and more often. And we’re using these a Power Automate, Power BI tools to do a better job attracting some of the trends which we’re seeing when we’re closing these deals. And that’s been really helpful for us to then demonstrate to our senior sales leaders the impact which our legal team is driving to help close these deals as well as senior members of our legal team.
As we wound down our talk, Dennis and Jason left us with a couple of parting thoughts. The first of which is that change is hard, but lawyers just like everyone else have to change as times and circumstances change. Sometimes lawyers just need to make the jump into using new tools and new ways of doing things. And all of that starts with a mindset shift.
Change is not easy. It could be tough. But we’ve all heard this sort of cliched quote that the only constant is change. And I think we’re going to see more and more change. We’re experiencing change right now through the whole COVID-19 crisis. And I think what it really means is lawyers need to feel better and more secure about embracing change, because we’re going to see more and more change. And I also think, we’ve seen a lot of change at Microsoft, especially over the last six years that Satya Nadella has been CEO. But embracing the right change can help you, and your firms, and your companies, and your legal departments be successful over a longer period of time.
A lot of lawyers, we all seek perfection in what we’re doing, but you don’t need to be perfect when using technology. Right? Just be sort of good enough if you will. Don’t think that you need to be experts in this technology. Just sort of try it out, ask for help when you need to get some help. You’re going to make some mistakes. And I would also mention that you’ve got to use technology of course. User adoption is critical. If you’re going to have any positive impact with technology you have to actually use it. It can’t be technology which you’re not using.
And then finally, just this whole notion about trust. I think it’s so important nowadays that when you’re looking at technology providers and vendors, make sure that you can trust them. Our CEO, Satya Nadella likes to say that, “Trust cannot be claimed. Trust can only be earned.” So make sure you’re taking your time to understand what does your technology provider do in the area of security, your privacy and compliance. Because obviously those providers are having access to your company’s data and your firm’s data as well as your data of your clients and you need to make sure that data is properly protected and secure.
Jason, any parting thoughts?
I think I would really just reinforce what Dennis said, that the transformation starts off with a mindset shift. We love technology and we try to bring so much of it to support our work, but it really is focusing on what Dennis was talking about of getting people into that learn it all rather than know it all mode. Activating that growth mindset, getting people feeling comfortable to not be an expert, to just embracing that we’re all on this journey together and that it is completely normal to have those mistakes. Especially right now, Dennis said it well, but in many instances perfect is going to be the enemy of good, because we’re not going to be able to basically tradition our way out of these unprecedented circumstances.
And so having people be experimental and trying things and learning things and having fast iterations is going to be critical to the adaptation for organizations, because we’re going to do stuff and we’re not going to get it right but we’re going to learn. And so trying to come up with a full planning arc for a situation that we haven’t really wrapped our hands around, that’s probably not practical. So getting people in that right mindset to be adaptable and to learn quickly and to bring that back and share it with others so that if people are stepping on bear traps, it’d be great to have a map of the bear traps. So that’s why putting information in shared space is so critical.
And the other thing I would reinforce is if we’re honest, many organizations have already purchased a lot of technology and so a lot of value can be had by just having a better sense of maybe what you already bought. Again, there’s a lot of goodness in the tools and capabilities that you probably already have in your stack. And so taking a little bit of time to go see like, “Oh, I’d never really played around with that, but let me go take a look.” I think that a lot of organizations can unnerve a ton of value that if we’re honest, they’ve already [inaudible 00:32:48].
Fellas, appreciate your time. Dennis, you have a great blog, which I’ll link to on the episode page, In-House Consigliere. People should check that out. If they want to get ahold of you, how can they do that?
Sure they can email me. It’s Dennis, D-E-N-N-I-S-G-A, firstname.lastname@example.org.
Jason, I mentioned earlier, you have a good podcast, The Business Law Podcast. I encourage people to give that a listen, and I’ll put a link to that on our episode page too. But if people want to reach out to you directly, how can they get in touch with you?
I do a decent job with staying on top of Twitter, so if people want to tweet at me @smuckwell, they’ll probably get to me.
Well, that’s it for another edition of Technically Legal. We appreciate you listening. If you want to subscribe, you can check us out on most major podcast platforms. If you want to get a hold of me, you can email me or catch me on LinkedIn or Twitter. Stay safe out there. And until next time, this has been Technically Legal.