In this episode of On Record PR, Gina Rubel goes on record with Jason Barnwell, an attorney in Microsoft’s Corporate, External, and Legal Affairs department. He is General Manager for the department’s digital transformation.

Jason’s team focuses on creating the future of Microsoft’s legal practice built upon Microsoft’s technologies. They partner with Microsoft’s legal professionals, internal engineering organization, and other actors in the legal ecosystem to develop culture, skills, and technical solutions that power legal services innovation.

His previous roles at Microsoft include leading the Legal Business, Operations, and Strategy team, leading the Open Source Software practice group, and counseling the Cloud and AI Platform Business. Prior to joining Microsoft, he was an associate in the Emerging Companies practice group at Cooley LLP. Before entering law school, he worked as a software engineer developing enterprise software.

Jason serves as Chairperson of the board of directors of the Pacific Science Center and on the board of directors of the Corporate Legal Operations Consortium (CLOC). He earned his B.S. in Mechanical Engineering from MIT and his J.D. from the University of Southern California School of Law. He hosts the Business of Law Podcast. He is passionate about technology and still codes when his work permits it.

Why should listeners care about tech and innovation in the legal industry?

That is a question that a PR professional will go in on the hunt with, and it’s a fabulous question because it really gets to why should people care really? Why should anybody care? And let’s break that into two pieces. If you are in our industry and you’re a provider of legal services, you should care because you can create a lot more value for your customers and partners. If you thoughtfully apply technology, innovation, really adaptation to your service offerings, you can create more value.

That means you can earn the privilege and the right to potentially bring more value back to your organization. So those investments can create real returns and make your business more profitable, and they can help your business go after new business. Even better, if you thoughtfully apply what we’re talking about, it can make the experiences of your people more fulfilling and so it really does create this virtuous cycle.

Now, one thing I find interesting is when people are on the provider side, look around and they see who they regard as their competitors, not making those investments, they think, well, I guess I’m safe. And I think that is an overly narrow view because, it is dangerous to presume that the competition for the future is going to come from an organization that looks like you and it looks like your organization. Because we’ve seen again and again, it probably won’t.

If people are taking comfort because they go and they talk to the people who they regard as looks like them, are like what are you doing? Oh, you’re not doing anything, I guess I’m safe. I would really caution people to avoid that trap because we see that happen again and again. And I think people are skeptical of well, is anything really going to change because we’ve been doing this thing for a long time, and it hasn’t changed as much as we would expect.

The thing I would offer to that is, yeah, things are changing and specifically, I think we’re at a place where capitalism in our context is just not going to allow us to keep doing what we’re doing. The demand criteria for our customers who are on the business side it is ratcheting up so high that the back pressure is really drawing us forward. If you look at the investments that are being made in the businesses that are the upstream from us and the capabilities that are coming online, it really will not allow us to sit still because we will have to adapt to meet their needs.

In a nutshell, it’s like look, you should care because it’s good for you, and you should care because it’s good for your people, and you should care because it’s good for your customers and they’re not going to give you a choice to not care.

Can you tell me a story about where a law firm did something innovative that impressed you?

Yes, I will not name the firm because I have not gotten their permission to speak on it, but I am working on something with a law firm right now that absolutely delights me. They are making investments to solve a problem that we have and they’re not doing it in the normal way that law firms show up with, which often looks like this. Hey, you just tell me what you want, and when they say that, nominally sounds good. It sounds very service-focused and oh, I’ve gone to every client responsible, but what they really mean is you do all the thinking and give me all the instructions in painfully granular detail to solve this problem.

I will somewhere between faithfully and grudgingly execute on that. This firm that I’m working with is going in the exact opposite direction. What they are doing is they are focusing on, hey, well, what is the problem? And not just what is the instant problem, but they’re snapping out a frame and they’re saying, if we were going to generalize this and create a system that did this for you, what would that look like?

That kind of expansive view and really making the investment before there is a lot of work behind, it is something that is so noble, and it made me so happy that I ended up sending a note to the firm-wide managing partner and the relationship partner saying, look, I do not see this happen very often. And it’s kind of amazing and I’m completely delighted. The other thing that’s novel about how this engagement is playing out is, the people who are doing the technical work are leading this part of the engagement.

Typically, what happens is you’ll have the relationship leads who are almost always attorneys feel like they must have their hands in everything. And there are times and places where that’s completely appropriate, but in this instance, the firm saw that, okay, what the client needs here is some technical development. And we could stand in the middle of that and do the things that we do, but it would be better for the client if we let our businesspeople and our technical people take lead on this and we will support.

Seeing that kind of pattern, if law firms can do more of this, we will see way more meaningful innovation and capabilities start to show up. So that is an example that I’m experiencing right now, that is absolutely making my heart sing.

Gina Rubel: That is fantastic. What’s coming to my mind is, here is a law firm taking a technology approach with a technology client and not being intimidated by the fact that you’re a technology client, but rather saying, let us bring a solution to the table. I think that’s what I heard you say?

Jason Barnwell: Yes, and we are probably more adept at technology than many clients, but the problem that we’re trying to solve lives all over the place. I wish I could go into the details at this point but the problem we’re seeking to solve is something that is a shared problem, and we’ve been very explicit with this firm. If you develop a really good solution on this, you are welcomed to go deploy that with other clients, because it’s not a proprietary thing for us, it’s not something special that we’re doing. Quite the contrary, if we can get more client side folks operating in the same way on this task, if we can coordinate and collaborate and standardize our approach, then suddenly, the cost of this specific work goes down significantly.

We’ve been very explicit that, if you can go find somebody else who is one of your clients who wants to buy this from you and to do engage in this way, we are very happy for you to go do that.

Gina Rubel: I know this is cliche, but the idea of win-win is so important in that, and it comes down to culture and we’re going to talk about that.

What do you expect from law firms as it relates to legal innovation? Where does it start?

Where to start, that’s a tough one. It really starts with thinking differently about how you create value for your customer and let me try to unpack that a little bit. I think when I look on my training as a legal professional, I was selected for, trained, recognized, rewarded, and promoted in the early phases for being highly reactive. There’s an instant need, do put insane effort against that to deliver the outcome as quickly as possible, without really thinking about how much resource did it consume and will they be asking for the same thing again.

The starting place is, start developing the capability to see patterns. Attorneys are really, really, really, good at critical thinking, which is necessary for doing legal work. The ability to have a sharp lawyer knife that lets you dissect issues and really cut them so finely that you can say, “Oh, well, Gina, I know these things look the same, but they’re not,” that is critical. But what we need them to do is start thinking about the systems and pairing the systems thinking with the critical thinking.

Looking for patterns, looking for how pieces fit together, and one of the challenges is doing systems thinking work, which is really a planning exercise. Requires you to reserve some time after you did a thing, to step back and look at it and be like, “Oh, did we do five of these before this? Are we going to do 50 of these after this? Okay, well, so what are the patterns?” And now the challenge we have is, if you’re a critical thinker immediately you’ll be like, well, we did five of these before, but each of these was different this an abstain though.

Well, we suspect that really, when we start looking at the bigger picture and the bigger frame, there probably is at least some pieces of these things that are similar so let’s at least focus on that. Going back to your question, I think the starting place is get people in the right mindset to think about looking for patterns, looking for repetition. And in many instances, what that means is partner them with talent that has the proclivity for that.

If you have made someone an elite critical thinker, it might not be realistic to expect for them to immediately pivot to. And now I will look for patterns, and sameness, and platforms and all the things that are wonderful. It may make sense to think about how you combine your talent set so that you have the people who are these amazing, critical thinkers with real depth expertise in whatever the legal issue is. With a complimentary set of skills that can really spot the patterns and then start thinking about how you can solve this on a systematic basis. So that gets into a lot of other stuff that we can get into if you want. But I think that would be my starting place.

Gina Rubel: I love that. I still remember, and I’m dating myself 30-plus years ago, taking organizational thinking as part of my international business training. One of the things that I didn’t see in law school was, this idea of organizational thinking and thinking through what you’re talking about, patterns, repetition. As an agency owner, we do this on the corporate communications side all the time, we have templatize where we can. It’s interesting because, we do this for our clients all the time, but I didn’t think of it in terms of legal services and the delivery of legal services. Now, I want to create a course, a CLE course on organizational thinking for lawyers.

Jason Barnwell: That is spot on, and there’s a podcast that people will not be able to see it, but I’m going to go into my bookshelf right now. I’m reading Designing Dynamic Organizations. I cannot co-sign what you’re saying strongly enough. That one of the things that we do not get in our training as attorneys is really thinking about how do you coordinate the work among people? What we are designed to be are, low drag individual contributors who come together periodically and often begrudgingly okay, let’s share information and work together.

But if you look at our culture it really starts off with a place of being an elite individual contributor. If you look at law firms, the people who end up in many instances running them, they were amazing individual contributors who built a bigger book of business and probably had some relationship capability. But in many instances, they do not delight in managing people, supporting, what they look for are people who require the least support possible, basically people who look like them. And then, they just kind of keep bringing people in until they find the right people that they’re kind of like who can fit in the sockets and then okay, I guess it’s good.

Gina Rubel: It’s interesting because as a CEO of a law firm marketing agency, that was my biggest challenge early in my career. And I’ve read a book called The E-Myth Revisited, which I don’t know if you remember it. I mean, I’ve read it 25 years ago, and it wasn’t about e-electronic it was about really creating systems the same way franchises do. And I’ve recommended it to so many lawyers because we are told bill this hour, bill this hour, bill this hour, bill this hour. And yet if we can create this dynamic organizational thinking, I’m going to have to get Designing Dynamic Organizations, I just wrote that down. It has helped me so much in running a business, and I can see how with this story, the example that you shared, how law firms can provide better value and over time, be a better partner and then, what they say is retain and acquire more business from clients. You do that through innovation.

When we spoke in preparation for this podcast, you shared your thoughts about scale. Can you tell our listeners what scale means and your expectations of outside counsel?

I started off as a software engineer before going to law school, and I thought I understood scale. But it wasn’t until I came to Microsoft that I’ve really got a view on what that means. And I’ll be honest, when I was an attorney at the firm, I don’t think I ever left the factory floor and got up on the catwalk and looked down and thought about what are we making here? And what are we producing? Supporting engineering groups that were really going after real scale as their primary business counselor showed me that scale is thinking about growth in orders of magnitude, not fractions, right?

People are often like, “Oh, I want to get 5% better,” which is a meritorious goal. But you must think about scale and put yourself in the right mindset for what that means. The thing that I’m going to be talking with people about over the next year is, we need to figure out how to create 10 times the productivity we have now, on roughly the same amount of human capital that we have right now. The business that we serve, those are their ambitions and I do not expect that the CFO is going to say, “Well, gosh, that business over there seems to be able to figure out how to do that. But dollar special, I’ll tell you what, you’ll get 10 times the headcount.” I just don’t think that’s going to happen and it shouldn’t because, if we’re honest figuring out scale, throwing more humans at the problem often doesn’t work. You have coordination and communication problems that start to become challenging. When we start thinking about what scale means, it meant sot put yourself into the mindset of if I had to figure out how to do 10 times as much of this, what would I do? Then here’s where it gets very hard, to do that you often have to unmake things.

You must cannibalize existing lines of business. Ask, what’s the stuff that we’re going to let break? That’s especially painful for attorneys because in many instances, what we’ve been trained to do is to never let anything break, over function however you must so that nothing ever breaks. Because there’s nothing worse in the world than somebody saying, “This is broken.” It turns out when you are making new stuff, sometimes you must break things.

What you really need to do, and this goes back into some of the concepts you were starting to poke out is, if we can create organizational structures that have psychological safety, that have good communication, we can holistically understand what we are going to allow to break, and it’ll be okay and then we communicate that among ourselves. Then what are we going to make that creates this new value stream that makes it worth dealing with a little bit of, loss or dissatisfaction or what have you on the other side?

You’ll notice that nothing I’ve said thus far has anything to do with technology, right? This is just thinking about how are we going to interact and inter-operate as humans, to build a new approach to how we do this work that can go from 1x to 10x. Bringing in those systems thinking that we were talking about earlier, how do the pieces fit together? Because if we really think about this, so let’s try to net this out as best we can. Our greatest scarcity is the attention of experts, of human experts, and so everything that we’re going to do to go after scale is going to treat their time, and attention as the scarcest resource.

We will do everything we can to take anything that doesn’t require that expert’s attention, and we will push it into a less scarce resource. And that can be other humans, that can be humans with playbooks, that can be templates, that can be machines. There are many ways to get there. But it really is the thoughtful application of thinking, “If that’s my greatest scarcity, let me do everything possible to protect that.” And that’s how we’re going to try to think about scale for our practice.

Gina Rubel: What’s fascinating with that is it is the hardest thing for lawyers to let go of the control of every aspect of something and focus on what they are most expert at, which leads me into a question that I hadn’t originally planned to ask but I think it’s important.

Is it more important for you to have a law firm that has a full-service and you can go to other parts of their firm, even though you know that the certain part is what they do best, or are you going to seek the best of the best in each area and have them collaborate, or something other?

 The true expert on this is my colleague Rebecca Benavidez who leads our law firm engagement strategy. She’s our director of a legal business, she is world-class at this. What she tells me is that, really what we need are experts in a thing that they do, and we can basically piece together what we need. Now, having said that there is a challenge that occurs, which is to do many types of work well, you need to understand our business, like every client, we are weird. We have all kinds of idiosyncrasies that are just like, why do we do this? Well, it’s a great question, not sure exactly how we got here, but we’re here. So, one of the things that we do benefit from is repeat play so that you can learn our idiosyncrasies and over time you can instruct us on, “Hey, if you could be a little less weird on this, we could do this way faster, way cheaper, way better.” But I think the short answer to your question is, we don’t really require full service firms, we can typically piece together what we need.

However, where we find a partner that has invested deeply in understanding a certain type of business, it’s often efficient for them to do the adjacent work too. In many instances, it’s because they’ve done the hard work of understanding us and what we care about and what we do. And then look, if it’s run work, if you can do the adjacent work cost-effectively and you can do it well, then you will probably get some of that work too. Where it turns into a situation where it is elite skill that is required and there’s only certain organizations that can do that work, then we scale them up.

We teach them about who we are and what we need, but we really do try to bring a partnership mentality to this whenever we can that again, looking at the patterns presumes, if this is a repeat play situation, how can we start knitting together connective tissue that makes the next ask efficient. Sometimes that’s relationships, sometimes that’s processes, sometimes that’s tools what have you, but we try to take the long view on this as best we can.

What I believe you said in a very concise way, you’re looking for industry and business expertise?

Yes. I would say, there are some practice areas that are so unique that we will go find the best person in the world in that specific practice area. But for the 80 to 90% of our work that is run business work, it goes back to exactly what you’re talking about. What’s funny is if we’re honest about this, when you talk to a lot of law firms, and I think they’re changing on this, so I’m going to paint with a broad brush here. They will show up and they’ll say, I want your bet-the-company work. And a well-run business, ideally does not have a ton of bet-the-company legal work, that is not the goal.

What we want to do is we want to run the business and run it well, and so it is great that people have that kind of focus, especially where there are impacts things that we absolutely must get right. But most of our spend with outside counsel is by design run the business work. At that point, it goes back to exactly what you said, having real facility with how to do that work well, and what are the issues we care about and how do we think about solving them is in many instances important because it goes back to this concept that we’ve been talking about of scale. Which is, what we’re trying to do is boil all the weird stuff into a more common set of things that we do, because that’s how we scale to do the work well, right.

If we’re trying to get out of the situation of trying to think of everything as unique and different when that’s not the case, and so looking for partners that really understand our business and can help us spot those patterns and find efficient ways to do the work, I think they’re going to get more of the work.

One of the things that I read in your bio is that you work to ensure that the law firms assemble teams of talent and diverse perspectives. Please tell us about your experience, observations and expectations regarding diversity, equity and inclusion in the legal profession.

Ae are as a profession struggling, and I think there’s a few reasons for that. One is, we just don’t love change, which a lot of what we’re talking about is a new way of thinking, a new way of seeing the world and that requires us to adapt our mindset. You have many people who have done exceedingly well in their profession, thinking about the world the other way. When we show up to them and say, hey, maybe you should think about this a little bit differently and they’re like do you realize I’m very successful, I’m good. Okay, so I think that’s an issue.

I think another thing that shows up is there’s just a lot of, I don’t know how to say it other than a meritocracy narrative that says, well, maybe the reason these things are as they are, is because it’s already been fully optimized. That’s a very narrow view on how we got here, and it really does not embrace that we are operating in a system that has a lot of skew and imbalance all over the place. That is a real issue.

We have so much work to do. The thing that I suspect will get us unstuck on all of this, it goes back to the business side of this which is, as we get better at ascribing the intrinsic value of the work that we do, we’re going to have more clarity. I believe that proves out that bringing diverse perspectives to our problems yields much better outcomes. If you go look at, I think there’s a bunch of hippies at this place called McKinsey that have done all this research that says this.

We will start having systems that allow us to start seeing, oh, this was the work, these were the outcomes, this was the team this team represents all kinds of perspectives and capabilities and that’s interesting. The reason that I have real conviction that it’s going to prove out that way is, increasingly the work that we have is less purely technical. The problems that we must solve are often not linear problem-answer solutions, what they’re called is adaptive problems, which means they are often a set of problems that operate in really a social space.

If you think about, for example, an issue like privacy, it might be tempting to think that privacy in the technology context is something that is this kind of linear function of, tell data subject X and adequacy happens if Y so forth and so on. That’s not what’s happening here. What we have is an evolving set of capabilities from the technology side, an evolving set of needs from really the consumer of technology side and then you have regulators who are trying to marry these things up.

It’s not like it’s this linear system of pool balls on a pool table. What’s happening is things are interacting with each other and to navigate the optimal solutions out of that, you need many perspectives. And that’s the pattern that we’re going to see more and more of on the work that matters, especially as we boil the more kind of standard technical into other ways.

What we have are adaptive problems now, they’re not these technical problems. And adaptive problems have these technical elements and as much as there are questions that must be asked and answers that must be given, but what makes them more complicated is they exist in a social space. They require the interaction of many parties who bring different perspectives and are trying to solve for different things. What we expect is that people who bring a broad set of perspectives with them are going to be able to do perspective taking and have empathy that allows them to navigate that space better and to really do it well, you’re going to have to bring together many people.

You’re going to have to kind of coordinate and collaborate and do all the things that we talked about earlier that we’re not always great at. The net of this is that we really think that all the things that come out of DEI work have a real business imperative. And they prepare us as an organization to do the work that is coming more effectively because, the types of problems that we’re going to have to solve are not going to be these linear question-answer things, which we’re going to move into more scalable approaches. It’s the noble, the new, the weird things that are on that frontier that I think more people want to be spending more of their time on anyway.

To do all those things, the only way you’re going to gain true emotional and cultural intelligence is to have diverse teams. Your end user runs the gamut of every culture out there, and so without understanding the end user and being able to really have that empathy from the emotional intelligence perspective it almost goes to say, how could you do the work?

Our mission is to empower every person and organization on the planet to achieve more. If that is your ambition you need to reflect the variety, the diversity of everybody who you seek to serve, and you need… Again, inclusion is such a huge part of this, because it’s not just making sure that you have representation, it’s making sure that the people who are there have a meaningful opportunity to contribute and bring what is special and different and unique to the problem, solving exercise.

If you’re merely bringing those people there and asking them to bake themselves into the shape of the people who are already on board, then you’re not going to get the best of them. Ultimately, you’re going to run them off because it’s well, now I’m having to cover who I really am and my ability to truly contribute so why should I be here. I am in absolute agreement.

Why is storytelling important to the practice of law and what kind of hire did you recently make as it relates to storytelling?

Humans aren’t great at absorbing facts. It’s funny that we’re moving to a data driven world and most people, they don’t really love being bombarded with data because we’re humans. We evolved to transmit knowledge and insights through stories, the narrative. That is as cave people scribbling things on walls. We were telling stories because that’s how we are designed to ingest and transmit knowledge and information.

We should honor that. We should embrace that there’s this amazing cognitive capability that humans have. Our biases that we often are concerned about, one of the things that humans are good at is figuring out inferences across weird spans, they will put things together now, often that walks us in the wrong direction. We must be mindful of that. But that is one of the powers that we have, if you can give people actionable information.

That’s why we focus on stories so that we can take what we learned from data and from information, and package that up in a compelling narrative that attracts people’s attention and then helps them make a better decision. For our team at Microsoft, we hired a storyteller, and her job is to help our people find their place in our innovation journey, because it is not easy to have been practicing and doing your thing for 5, 10, 15, 20 years; however long you’ve been doing it. And then have people say, hey, we want to think differently about that.

What we’re trying to do is take the ideas, take the information, take the insights, and help rebuild an identity, a cultural identity by effectively giving people a new narrative that they can feel good about, and that they can see themselves in. Because ultimately what we are on is a journey, a journey of change and adaptation and transformation, and to give people a way to direct themselves on the journey, because we’re not going to give people a paint by numbers approach to their practice.

We need to give them a projection of what it looks like for them to be successful in the thing we’re trying to create, because then that lets them make it for themselves. It gives them agency in how we’re going to build our new experience. What we find is that command and control is not super effective in that, because again, this is a creative exercise. If we can give people a story that is meaningful to them and that they feel good about, then they start walking with us. And so that’s why we think storytelling is critical for the exercise.

Rapid fire:

What is your favorite book and why?

My favorite book right now, because it changes is a book called The Ministry for the Future, which is written by Kim Stanley Robinson. It is a fiction book that takes the current vector of climate change and starts to project out what might the world look like if that continues a baited. And then it posits that, what if there was an organization whose primary responsibility the reflects the perspective of people who do not yet exist, and who are impacted by our decisions now. I’m not going to pretend that it is the most uplifting book, but if you are looking for something that will give you a different way to think about the world and the problems that faced us and the opportunities, it’s really, really compelling. And I’ve been talking to a lot of people about it lately.

If you could meet one person who’s alive today, who would it be?

I would like to meet the person who will lead the world’s most influential organizational construct 25 years from now, because I would love to see what that person thinks about, how they are viewing the world. And I realized I haven’t given you a name.

What is your superpower?

I seem to be able to care about things that bore most people to tears.

What word do you find most distracting in the English language?

Tolerance.

When you were a young child, what did you want to do when you grew up?

Space Shuttle mission commander.

What one piece of advice do you have for our listeners?

Be curious, stay curious and ask why.