Humanizing Law Firm Work with Jason Barnwell at Microsoft | Pearls On, Gloves Off

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Hello everyone, and welcome to Pearls on Gloves Off. I'm your host, Mary o', Carroll, and today I'm chatting with a dear friend, Jason Barnwell, who is a real leader in the world of legal transformation. If you don't know him already, he is on the board of directors at Clock, where we serve together and where I got to know Jason very well. I can tell you that many of us refer to him as the smartest guy in the room. So now that I've embarrassed him and he's laughing because he really is super smart, let me give you a little on his background. So Jason is an attorney in Microsoft's corporate, external and legal affairs department. He is a general manager for the department's digital transformation. And 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. And before entering law school, he worked as a software engineer developing enterprise software. He earned his BS in Mechanical Engineering from mit. Told you he was smart and his JD from usc. So, Jason, welcome to the show.

Mary, thank you so much for having me.

So you have an unusual title. What is GM of Digital Transformation? What does that mean?

It means that I am a professional cheerleader. So one would think that a title like that would imply I spent a whole lot of my day doing hardcore technical platform architecture. And that is certainly some of my day. And it's a lot of fun because when you work at the candy store, you get to taste all the best candy.

Yeah.

But a lot of my work is really, I would say it's a business and leadership role in as much as I'm trying to help us figure out what is the future of our practice, how do we start walking in that direction and how do we get people ready for the journey? So I'm being a bit glib when I say cheerleader, but a lot of it is really helping us create the vision for our future state and thinking about how what does that journey look like and then really getting people ready to go. So it is, it's a very horizontal function. Yeah, yeah. I connect a lot of pieces in the department, helping us find commonality patterns because the other challenge we have is, you know, the company we work for as exponential growth, ambition and capability. But the resource allocation to our department, we should not expect that that's going to grow exponentially. And so now we're trying to square that circle and fig, figure out within our resource envelope, how are we going to satisfy the needs of this growing business? And so, yeah, my job is a lot of fun.

Yeah. And how did this role emerge? Did you create this job? Did it kind of naturally evolve from some of the more traditional legal operations and strategy roles you've had in the past?

It's very much an evolution of things that I've been going after for a long time. So. So if we go kind of way back, I got into what I would call the business of law game probably close to six years ago. And I think that's about when we met. And I was really the first role that I focused on was law firm engagement strategy. So our department several years ago decided, you know, we have pretty substantial engagement with outside counsel firms, we should think about how we might engage with them differently. And then that evolved into a role also leading the legal operations team. So that's when the legal business operations strategy came together. And then a few years ago, the GC was like, hey, you know, would you be interested in maybe spinning yourself off and really focusing on digital transformation? And I looked at the team we had and the people who were leading legal operations and legal business, they did not need my help. They were, they were fully realized folks. And so I was like, yeah, you know, I think this works great. And so it really was kind of the evolution of kind of getting brought into the business of law side of things and then stumbling around and finding new and interesting problems and then kind of expanding that into other spaces and then being asked by the department to go focus on something that was of specific importance. And so that's what got us here.

That's so great. And I love the tribute to your success in the department and how you set it up and you trained and mentored probably your deputies and your right hands when you were doing legal operations such that it was a well oiled machine and you could step away. A lot of folks get nervous about their job security if they hire smart people who can do the job. And what you've proven is that you set it up for success. You sort of optimize yourself out of a role, as I always say, and that is what success looks like. And then doors open to other things. They don't close on you, right?

Not at all. So that's where I think that it is very beneficial to be in a place that allows a certain amount of entrepreneurialism. Because if you can go create more value and new types of value, then the number of doors starts to multiply and the thing you realize is that there is way more cake at this party than I could ever eat. And so you're like, you know, we should bring some more people to this party and we should bring not just people who like to eat cake, but also like to bring other people and share cake. Because guess what? We can always make more cake.

Oh, there's always cake. There's so much.

There's always cake. There's so much cake. And so I'm always intrigued by, you know, the, what are effectively the cake slicers versus the cake bases. Bakers, Right?

Yeah.

So there's some people that are like, they think that there's a fixed amount of cake in the world. And they, they seem to care a whole lot about, like, well, let me, let me, let me think very deeply about the slice of cake that you get, because there will never be more cake. And I need to make sure you don't get too much. And then there's other people like, well, I'm going to be making another cake tomorrow, so you can have a little extra, a little whatever. There'll be more cake. So I'm not going to fret too much over that. And I don't know that that's the best analogy in the world, but when I do think about our work and the opportunities that come from it and the opportunities that we can manufacture for ourselves and others, it's kind of a cake baking party in our space. Because the problems that corporate legal departments have are so righteous and they're so grand and they're expanding as the business that we serve starts to grow, that it's just a. It feels like it's a nonstop cake party.

Mary, it's so true. So true. I often tell people the hardest part of the job is figuring out which problem to work on, because everywhere you look, there's another problem worth fixing. So when there was like another team that was going to come in and infringe upon some of the work that my team was doing, I was always like, oh, you want this cake? Please have at it. There's plenty of other things we can work on. So that's, that's a great attitude. Okay, so let's rewind. So you and I, you mentioned when we first met, and I was just thinking back, it probably was about six years ago ago, and you and I met at oric, a big law firm. I used to work there. And so we were both invited to speak on a panel together. I think it was internal. We were speaking to their attorneys about kind of how to work better with clients. We were the client panel, et cetera. And I think at the time, you were in charge of the law firm relationships. And I remember being on that panel, you speaking, and I kept just nodding my head up and down and thinking, wow, this guy has some really good things to say. Walked up to you, and I said, you, I must know you and you must be part of the community. And I sort of started dragging you into things. And I don't think now, many years later, even though we're not even on clock together, I'm still dragging you into things on the sides here and there, so. So I hope you're okay with that. But I think that I know good talent and good people when I see it. Going back to that time, though, when you were managing outside counsel, and I just remember there were some really thoughtful things about how we can all work together. What is some of the advice that you would give to law firms? And I guess bigger difficult question is, do you think that they're capable of changing? And when do you think that change will happen?

Every organism is capable of some amount of change. It just requires the right set of constraints and incentives. And I think that law firms are going to. So they're starting to change mostly around the margins. But one of the biggest challenges for them is their core business model is not designed for the class of really, I would say, run work problems that I think represent the growth in the industry. So if we just say, if we just accept that, you know, there's a slice of really, truly complicated needs, all the fanciness and the giant brainitude of legal professionals, that slice is not going to go away. And it will very likely remain in the purview of law firms. There's a huge, much, much, much larger tranche of work that sits underneath that that is growing at a much faster rate than, I think, the premium stuff. And I think the hard part for law firms is that to go after that other work, they will need to fundamentally resource that work differently. The models that they use are really not designed for that. And I think many of them don't want to go for that work because it doesn't have the right pricing characteristics, it doesn't have the right premium. And that's okay, that's great. But the challenge will be for them as buyers, as we get better at understanding what is the real value of the work that we're asking a law firm to do, and we start unbundling some of the things that are kind of stuck together, we may realize that the volume of Work we have all been sending to law firms at a premium rate that doesn't really make sense. And some of it is absolutely premium work and should continue to command that. But as we get more savvy as buyers and understanding how does the work that I'm asking for translate into both value, but also what are the characteristics of this work? Is it really growth work that has truly novel characteristics, or is it run work as we get more disciplined about really sorting that into the right tranches? Some law firms may find that the work that we used to send to them will not be sent to them because we start to realize that paying a premium labor rate for that doesn't make sense. And that's when we start thinking about, well, okay, if it doesn't go to law firms, where else might it go? And we can imagine that that work might start going to other types of providers, both on the really the labor side, but also technology. That's ultimately where I think this goes. As we become more of a. So as the department I work in becomes more of a business, our business has to operate at scale. We need to start looking for other ways to do that work that truly scale, that build on really platform economic, and that entice us to probably make larger fixed cost investments, but that have better marginal unit costs. And so as we start to get smarter about that, then I think we will do a better job of broadcasting more of the signal that is our demand characteristics into law firms. And they will evolve. I fully expect some of them will evolve and some of them will not. And that's just business. That's, that's how these things play out. So that's, that's kind of where I think things are going. But you know, I'm wrong a lot, so who knows?

Yeah, yeah, it's, it's complicated. And it's interesting also that I think we, you know, legal ops has put a lot of pressure on the industry to, to do more. Right, sourcing. That's exactly what you were saying. Right? Leveraging technology, bringing stuff in house, going to alternative service providers, going to different types of law firms. And I would think that that would have had more impact on changing the law firm business model or how they work faster. Because there's more, let's stick with the analogy. There's more people eating the cake, people taking slices of that cake. But the cake keeps getting bigger, which is why I think that the law firms are still able to report record earnings and record profits per partner every year. Even though I think the dynamics of how Big, their slices is changing. Is that kind of. Would you agree with that?

So I think that law firms are in. They're just in a classic innovator's dilemma problem, because the work that they get now really has incredibly attractive margins attached. And so it is. And the way they're capitalized, there's structure. The structure of a law firm, the way it's capitalized is designed to basically distribute out all the profits.

Right.

The owners can only be lawyers in the United States. So attracting capital is really hard. There's just all these features that serve them in one context that make it harder for them to really compete in other contexts. The reason that I think we have not seen them adapt or change, there's a few reasons. One is structurally, they're just in. It's hard for them to change. But the other thing that I think is impacting the rate of change is they are looking kind of left and right at who they regard as their peer competitors. And they're not seeing that much change there. And they're like, well, I think I'm still okay, because when I look left and right, they're kind of still doing the same things in many instances. I think they're not always looking at the direction of travel. And so if you look at the field of play and you say, well, we're only seeing minor incursions from the technology and really the cheaper labor side, then you might think like, oh, I'm in good shape here. And the thing I would offer is the nature of exponential growth curves is they look kind of flat initially, and then they pivot pretty quickly. And so you really want to look at that, really the acceleration curve on these things, not the current velocity curve. I realize I'm losing people now because I'm talking about math, and nobody likes math. But. But really it is one of these things where there's all these kind of natural phenomena that have these characteristics. So, for example, viruses, they start off with this like, well, and then all of a sudden they pop, and you're like, how did this happen so fast? Well, that's an exponential growth. And I'm not saying that we're going to see those dynamics in the legal business. But my hypothesis is that there are already early indicators that other service delivery models are gaining a bit of traction. But then when you start looking at of the genuinely interesting and transformative technologies that are starting to wake up, what we expect might happen is all of a sudden the change in adoption cost for alternative options could plummet. And one of the things that has kept the spend with law firms so stable is they're really great at building these relationships and specifically they're really good at understanding and not documenting the preferences of their customers. And so it's literally like you walk into the cafe and you're like, mary, give me the number three. You know how I like it. Right. And so that makes it very. The work very sticky. But as we start to have new and different tools that will help us start to really understand more of the fundamental nature of the work that makes it less bundled and more portable, then we should expect that some of that work is going to get loosened up. That's being accelerated by the constraints that we're having. So I can tell you that internally in our shop, there is an incredibly different appetite for value maximizing approaches. That was. It is a completely different situation than it was when six years ago when you and I met and I was having to go sell and I was sell internally and I was literally doing road shows and convincing people. And I think people are like, well, I mean these are good ideas, but do I really have a problem here? And let me tell you right now, internally, people are like, wow, the demand criteria for the work, like the volume is just going up at this incredible rate in large part because you've got all these new regulatory constraints that are making a lot of work more complicated. Then you just have the organic growth of the business that we serve that's just ramping up in large part because they are making their own digital transformation investments that are able to just really increase the organic. Yeah, the organic demand that they can push into our boundary. And then you just put in the general competition market of what's happening in the world where selling a dollar of value is just getting a little bit harder because we're all having to compete. And it's just this perfect stew of what's making our work hard. And people are starting to see this and we're starting to give people tools internally that to help them understand a little bit about what they're experiencing. And the net effect of that is me brokering conversations with new types of providers is so much easier than it used to be. It is just such a different story and a different feeling and it's a lot of fun.

Do you think that's true for other departments as well? I mean, I am seeing a lot of folks feel pressure from the digital transformation that's happening across their organization. Right. So every other part of the company is speeding up and doing more and using data more. And you Know, Legal is then feeling like, well, we better do something too. Or do you think it's a company like a Microsoft that is just kind of tech forward and open to constantly adapting and changing? I mean, or is it you've been there a while and been able to show the impact of this type of work? Do you think it's unique to your organization or do you think that's a something that's happening everywhere?

That's a great question, and I do not know, but I'm going to offer an inference or maybe an extrapolation. So one of the things that I'm seeing in our shop writ large is there, there is more discipline being applied to where incremental resource investment goes. And what I see happening on kind of a macro level is the folks who control resource, also known as finance, are really trying to get more disciplined about thinking, well, if I have an extra dollar to spend for the enterprise, where is the best place to put that? Because I could fund Legal, I could fund a new product, I could do any number of things. And so I think part of what is driving this new interest in being able to express what we do as value and tell a more compelling value story is coming from that larger kind of macroscopic change, which is. So let me tease out a little bit of what things used to look like and what they look like now. In the old days, I think we could just literally point to the business and say, man, this business that we support is growing so, so, so much.

Right.

And so we will need extra resources to do our thing for that business. And I think increasingly the people who control resource allocation are asking the question of, well, why? What would I get for you doing this or would I lose if I don't give it to you?

Right. And should you be getting better at doing that over time such that you can do more with what you have?

Right, exactly. So I suspect that other organizations are probably having very similar conversations. And so I don't know that for a fact, but the signal that I do get is people in other shops asking questions of a type that suggest to me that they're starting to feel the same kind of pressure to start having a more crisp expression of the value that they're delivering to the enterprise. And there's a trap. Right. So if anybody's in a legal department and they get into something that looks like, well, to get more resources, I'm going to need you to give me a data informed argument. It's like, oh, okay, well now I need to get some data. I Need some resources. Oh wait, it's a trap, right? So if you need resources to create data, you need data to ask for resources. You're going to be in a tough spot. And so that's why I think forward looking legal organizations, corporate legal organizations are probably going to want to get into a stronger data posture sooner rather than later. Because if you try to go after this later and you're caught flat footed and now you're in a, I need to go secure resources. What you don't want it to be is an argument that looks like something absolutely dreadful or horrible has happened. The platform is completely burning. So now I need the resources, which can certainly be effective. But I would much rather have the conversation that looks more like if you invest in us, I'm going to supercharge this business. I'm going to. So right now this business is going down these, these roads that bend and turn and all this other stuff. And what I'm going to do is I'm going to start designing the run work especially to go down a straight super highway that goes exactly where you want it to go. And we'll have all kinds of fabulous telemetry and other things that can help, you know, really support like we are smoothing the road, we are giving more compliant, faster, you know, time to realization of revenue. And if you can tell that kind of story, I think it's much easier, it's a more fun conversation to attract investment than oh, everything is a disaster and oh my gosh, we have to go clean up the Superfund site.

Right, Right. And so you're talking about how do you deliver or how do you show value to leadership, to finance, to the rest of the company that the legal department is delivering? And that is the question that we get all over and over. Right. How do you demonstrate your value? You're saying with data? Are there specific things that you are doing to try and demonstrate the value of your department using data? Are there specific metrics? Is it about year over year improvement? What resonates with folks?

I am running a few very small experiments and the thing that I am trying to do and that is incredibly hard or harder than I would like, is ultimately I would love to be able to express how the work that we're doing and the outcomes that we're creating ultimately translate into what I would call business native forms of value. That could be faster revenue, that could be more revenue, that could be, you know, you know, avoided cost, things like that.

Risk avoidance.

Yep, exactly. But the thing that I'm really trying to do, and I'm running one small experiment that I have to be a little bit vague about is there's a piece of kind of run compliance work that's not very high risk, but it's a. It's a useful part of our product development process. And what I want to show the business is that we are in the process of Delaware in a whole bunch of this, so that what used to be a, you know, you probably get your answer back in three days. I want to get the. The median down to about three minutes. And if we can do that, then effectively what we're doing is we're allowing that that product group to get more bats because they're not waiting for us to get an answer back. It's like, yes, you can do this, which is most of the cases, and you do not have to wait for your legal professional to be awake or for it to pop up in like, kind of their priority queue. You get a good enough answer to kind of hit the next gate really, really fast. And I don't think this is appropriate for all the types of work we do. But if we can get this into a posture where people feel good about it, then I think what we can show is anything that touched this piece of work is now accelerated by probably about three days. And if we extrapolate that over hundreds, thousands, however many units of work we do in a given year, we can basically say, you got to run the race much faster business. And we know that when you get to go do these things faster, we're basically giving you more at bats in the ball game. And then we can say, well, probabilistically, we think that there's a value that attaches to getting more at bats, because we know that however many at bats you get multiplied by some discount function has the outcomes that we're talking about. So I would say that we're still. It feels incredibly primitive where we are right now, but I'm starting to develop some thinking frameworks to help us start translating the investments we're making and the outcomes we're driving into. Again, I think what I really want is to be native business value. So not the kinds of words that we use in legal, like risk and all this other stuff, which is all very important and very real. But asking somebody else to learn our words and understand how we conceptualize these things feels less useful than, hey, I can tell you about why you care about this in your words and why you should support our ask to go get more resources from finance so we can give you even Faster returns and even better at bats.

And that's such an important part of our role is being able to communicate and work cross functionally and being kind of that liaison to translate between legal in every other part of the company. Do you work a lot cross functionally? What other teams are you touching day to day?

I. So it's interesting, my internal passport gets a lot of stamps on it. And so I ended up working with engineering and finance and compliance and trade and, and, and, and so the, the, the legal department, when doing its job well, I think is an inherently horizontal function.

Yeah.

That connects different parts of the enterprise together. And so that means that for the work I do, you know, there's a pretty large pick basket of projects that we can go after. And for reasons I don't entirely understand, my leadership kind of lets me have a certain amount of discretion. As long as things are going kind of in the right direction, they let me kind of do have some prioritization on the things that we pick up. And we actually do have some thinking around this. It's not just Jason's gut, but the net result of that is we end up playing in a lot of different spaces. One thing that we done that's a little bit different this year on my team is we noticed the last couple years we were getting a spread a bit thin. So we had a lot of projects. So the total number of projects was quite large. And I felt good about the projects we were taking on because we were learning so much, much. But this year we've been a little bit more disciplined. And what we're, what we're doing is we're platforming more. And so what do I mean when I say that rather than everybody gets to show up and spin up a new project, which is like 10% difference, we're starting to get more disciplined about saying, you know, we have something over there that's pretty good and it already works. And so what would we have to do so that you can build on top of that rather than us spinning up a new thing and creating more technical debt? So a lot of this is ultimately turning into a base layer set of knowledge management investments that solve some just forever problems like, who is the expert on this? Where might these documents be found? Can we start creating an internal, a coherent internal taxonomy to describe our stuff, just some of the basic things. Well, fair enough, but we're going to try to make it, it better enough that we can start burning down some debt. And we know we're going to get it wrong before we get It. Right.

But yeah, well, and that's, that's the key. I mean, we used to try to do that too because if you don't pay attention to your platforms, you're going to turn around and have 100 systems that you have to maintain and update and keep track of and keep integrated. And what we would, I would try to tell people if you can take one of your systems like you said, that work and apply it to something else that maybe it's not purpose built for, but it works like, I don't know, 70, 80% of the way. It's probably good enough and better than trying to find something that's going to be 100% for every team. And it just makes life easier in the long run. In your role, you've mentioned several times how leadership has been very helpful and supportive of your charter, lets you run with things. I feel like I was blessed with that in my experience as well, but not everyone has that. I've talked to a lot of people who are really struggling to get leadership by and are constantly trying to focus on changing the mindset of the folks around them. Is there, is that just the situation you walked into again? Microsoft and Google being tech companies? Or was it hard in the beginning and did you have to kind of work your way and build relationships and trust to get to where you are?

It was hard because even in a place that has technology affinity, the leaders are busy. They are busy people. And what you're doing is you're asking somebody to pay attention to something new. And the reason that your senior most leaders got to their positions and have been successful in the way they are is they're very good at ignoring stuff that's below a certain materiality threshold. That's how they get the most important things done. And so one of the mistakes that I have made and seem to repeatedly make is I express a problem using my frame. So my words, my perspective. And as I've done more and more of this work, I've gotten a little bit better at bringing problems forward with a descriptive frame that is native for them that starts to put the problem in a really a set of words and a thinking framework that attaches to stuff that they care about. And when you can do that, then you earn the right for people to pay attention to the problem. And so I will say that in many instances I'm such a nerd. And what I would do is I would build something. And I'm like, this solves a problem. And what I really wanted to do was show off My shiny new toy. And the person who is responsible for the productivity of, like, a huge number of people are like, that's nice. I don't understand why I should care about this. And so ultimately, what I've done is I've started to kind of reframe the conversation and say, look, you have 500 people who are currently working on this. If we could make them just 1% more effective, imagine the slack that we would introduce that would let you go do some other interesting things. This is a way that we might get to that 1%. And then people like, oh, okay. And notice I didn't say anything terribly grand. I said 1%. So if you can get people to say, like, on a big enough denominator, a small percentage increase in improvement gives me something useful to play with, then you. Then it becomes worth the conversation for them. But that's, I think, one of those things that I have gotten wrong. And when I. When I do a better job at it, I get way better engagement from our senior leadership because I'm now talking about things that they care about and that are worth their time. So that is. I don't know that if that's what's happening to other folks, but that's a lot of the reflection I've had to do myself to figure out. Like, I feel like I'm. I'm pointing at something, but people aren't paying attention. It's like, oh, I was pointing at the right thing, but I was using the wrong words to describe the thing I was pointing at.

Yeah. And that's. I think a lot of people struggle with. I'm working so hard. I've tried so hard. I did all the things. I structured my arguments logically, and it's not clicking with someone. Right. And then they're like, but I did all the things I was supposed to do. Why isn't this working? And, you know, the advice that I sometimes give is, every organization is different, Every stakeholder, and every person you deal with is different. And you kind of. The hardest or the quality you need to be successful in this role is figuring out how to get stuff done in your organization or with that person. And once you have that unlocked and without authority, it's great if you can get that empowerment and have that seat at the table. But even if you don't have it, if you can figure out how to get stuff done without the authority, then you win.

There's a bit of. And there's an interesting thing that comes out of what you're talking about, which is what you're really talking about, I think, is empathy, right? So you need to examine the experience of somebody who you may understand their job or you may not, right? And you need to put yourself in their shoes, often kind of guessing at what it is they're trying to solve, because in some instances you don't have access to. To that. So what you end up doing is you start looking at like, so what are the words they're saying? Who are they talking to? And so you do a whole kind of, like a lot of kind of inferential analysis where you're looking at kind of the stuff you can see. And then you're trying to build a model for how do they perceive the world, how do they make decisions, what are the problems they're trying to solve? If you're really lucky, you can just ask them. But in many instances, that person may be incredibly busy, or you may not have the relationship capital or what have you. And so in those instances, a lot of times, the most effective thing you can do is if you can't get direct access, you go talk to the people who are closer that you can and then ask them, like, so what is this person trying to solve for? What do they think? And the funny question that I've been posing to my team a lot lately is, so do people make decisions based on thinking? Do they make decisions based on feeling? Or both? Or is it like, is there some mischief? And I think your point is one that I've tried a lot and failed, which is like, I show up with a really great logical argument that has no resonance, there's no feeling to it. And so then I'm like, well, but I made this great argument. And it's like, yeah, but it did not have a narrative attached to it that anybody wanted to absorb. And so, you know, you basically put sawdust in their mouth when you should have been giving them a slice of cake. And so over time, all that cake, all that cake. And so over time, a lot of what I end up doing is trying to make my arguments simpler, more elegant, and have more emotional component to them. Because the other thing that I observe is you're trying to get people to pay attention to something. You're trying to get the best of their intellect applied to a problem, make it interesting, make it compelling, make it relatable. Don't. You know, I made the mistake once of giving somebody very senior in the department a spreadsheet. And I was basically told, like, yeah, I mean, I don't want to spreadsheet. I want you to. I need you to explain why this matters to me. That's why you have your job and I have my job.

Exactly.

And so, as weird as it sounds, a lot of the investment that our team makes is in storytelling. Because when you take facts that point to something interesting and important and you wrap them in a compelling narrative, then people are willing. It's a slice of cake, not a quart of sawdust. And they'll gladly eat that cake.

Yeah. So you say empathy and storytelling, and I say those are very important. If those don't work, you resort to trickery and seeing how you can fool them. Interesting. Yes.

Well, I think all of these are part of the same toolbox, personally. Right. Because again, what you're really trying to do is position your argument to be something that can be absorbed. And there's many different ways to go about that. But if you don't understand what this person is looking at as indicators of value and interest, then you're basically, basically probably just getting lucky when it hits.

Right, Exactly. Okay, so what part of your background do you think has helped make you successful in your operation strategy, transformation roles? Because you, you are a lawyer, you are an engineer, you know, or was it some experience? What do you think has helped you?

I think the most helpful part of my background is I married a clinical psychologist.

Oh, so important. Yes.

Yeah. So she's been working on me for decades and trying to help me, thank God. So true, so true. I mean, look, you know, I'm, you know, 80% robot, and so she's been chiseling away at the roboticism over the years. But no, I think the most valuable experience for what I do now is her literally helping me understand the things that I could not perceive because I just didn't have the kind of connective tissue. But the really interesting thing is you can grow that if you just pay attention and are curious and try and practice and care, you can get better at these things. But, like, let's not get it twisted. I was a software engineer. Right. And, you know, I mean, I don't want to throw shade at my fellow software engineers. I still write software, but a lot of my early career work, my presumption was, well, I, the smartest thing I can, and then it'll all kind of sort out. And it is only as I've kind of, I think, matured and understand the world just a little bit better that I've started to understand that now, you know, that's not really how humans work. And turns out humans are who we serve. Humans make decisions. Humans are the ones that we really need to empower if we're going to do the most amazing things. And so that's why I put forward that kind of thinking, feeling question. And the other joke that I it's not a joke, but the mantra I throw at my team a lot, and I think I sourced this from jm, is that we're in the feelings business. Business. And so whenever we start to think that, oh, we're a technical build shop, it's like, yes, we build robots and our robots are cool, but the reason the robots are cool is because humans perceive that the robots are cool. And if we are not operating on that human layer, then we're not creating the impact we need to actually bring the business forward.

Yeah. This is a theme that comes up over and over in the webinars, the podcast, the people that I talk to. It is such an important part of the role. Another question for you, given that you were a lawyer in your role, and I talk to now a lot of lawyers, whether they're still at a law firm or they're in house, and they've now learned about this amazing legal operations and technology space, they would love to break into it, but there isn't a clear, regular standard path for getting into these roles. What is some advice you'd give for lawyers who want to make that transition?

So embracing that I'm a total weirdo and an extreme nerd, I'll offer a little bit of reflection on my experience. So I left the law firm not because I didn't like the work, not because I didn't like the clients, not because I didn't like the people I worked with. They were all great. I just didn't feel that it was aligned with the way that I was going to be able to deliver the most value. And so I showed up on Microsoft shores and I realized all of a sudden I had access to all the toys. And so I started dragging my colleagues along and they're like, so they were doing things in their way. Like, no, no, no, we're going to now drive all of these super necessary but low interestingness client requests to the SharePoint list I've created. And guess what? I have built this very basic kind of routing engine. So for a whole bunch of these, guess what? We never should have been doing this work in the first place. So it automatically sends them off to this other tool that they should just mess around with. And so what I'm getting at is find a problem, fix a problem. If you. So here the trap that people, I think, fall into is, oh, gosh, if I just work harder at the thing that I'm doing now, people will magically see that they should give me this opportunity.

Yes.

And I have a completely divergent approach on which is what you should. What I, what my approach was to take a problem, and sometimes it wasn't even a problem I owned and I got trouble. But basically this is a class of problems that I can solve for you and show people what I could do. And yes, it meant that I was probably working a little bit longer and a little bit harder because I had still had to be good at the job that I had. But ultimately most of the opportunity that has manifested me is because I protected a certain amount of my capacity to go do exploration work that didn't have a linear set of outcomes that I could point to. I was like, oh, this will, this will make something magically better. Or. And it's certainly in many, in many instances, it did not directly serve my day job, but it gave the people in my organization a view on the things I could do. And it wasn't constrained by, you know, my manager basically doling out some opportunity. It gave me the chance to go be an entrepreneur and literally go out on the frontier and find interesting problems and make them a little bit better, help other people tell their stories, pick up some new skills. And so if you want to accelerate your career and go faster on these things, I think it's really important to give yourself some agency in how you will actually have opportunities go after. Because if you're stuck in a situation where, well, I need someone to hand me an opportunity before I can show people what I got, that takes a lot of the schedule and the clock of progress out of your control. So I don't know that I have a very crisp and linear answer for you, but I guess I would really say act like an owner, be entrepreneurial, take some smart risks and show people what you got. And if you do that, then it seems like a lot of good things can follow. Right.

Just take, just start doing the role if you see problems and no one is going to ask you or tap you to do it, so just go do it and prove yourself and go from there. Right?

That's right.

Final question for you as we wrap up. What about advice for general counsel? As they're new to this world, they maybe haven't worked in a department that has a function like this, but they're curious and they want to start hiring for it. What advice would you give for Both how to structure it, who to hire, you know, how to get started in transformation or operations and strategy.

I wish there was a very linear response to this question, but I'm going to pull some lawyer nonsense and say it depends. And so let's talk about the things that it depends upon. So one of the most important things is to have a genuine and realistic understanding of your organization's culture and not the aspirational version of your culture that you.

The real one.

The real one. Because basically what you're doing is you're trying to. If it's a new function for you, what you're doing is you're adding a new organ to an existing body. And if you're not careful, the body will reject the new organ. And so.

Well said. Yeah.

And so you want to think about who you know. First of all, how am I going to justify the resources that go to this new organ? Because guess what? New organ needs blood. Right. And unless you are, you know, growing the amount of blood, that means that other people may feel like, oh, I don't get as much blood now. Right.

Cake.

Now my metaphors, you know, you're catching me at the end of the day, Mary. The metaphors are just all falling apart. So I would really take a very real inventory of the culture that you've got, but also really think about what do I need to accomplish and have a realistic expectation of I'm hiring this person in to achieve what and have a somewhat crisp view on that. If you can answer a few of those basic questions, like what is our culture now? What do I really need to accomplish? And then it's just as importantly, what do I already have that maybe I'm not taking advantage of? Because in many instances, it's not like the kitchen is bare. It's just got some things that may be a little bit dusty or maybe not used as much as they want. If you could start answering those questions, then you start to get a better sense of who you can bring on. I think the other thing that if you're a gc, you really want to start thinking about is what is the direction of travel for my internal ecosystem? And by that I was getting at this a little bit earlier. The other functions that are in the enterprise, what are they expecting of me? What kind of support should I expect from them? Let me be a little bit more crisp. If you already have great support from your IT or internal engineering organizations, maybe you don't need to bring in somebody who is going to focus on your technical platform management because you've already got that covered. You may have that person focus more on finance related things or what have you. And so this is again, shameless. Plug. I would say go look at the clock. Core 12. It is a really great expression of the inputs that an operations leader can bring to your business. And it lets you very quickly spot like, where am I strong and where am I weak? And perhaps even more importantly, where do I need to be strong? Because you know, strategy is always, is really thinking about where are we going? Yes, I know where I am now, but where are we going? And rather than driving with the rear view mirror, looking at that windscreen at the front, figuring out where, who, who do I need next to me to be my navigator, to maybe give me a kind bar, keep me hydrated, what are those things that are going to make me more capable of leading us down this journey? And if you start thinking about it in that kind of form, where it's really in its highest form, I think working with a person like me, we want partnership, right? If you want me to come in and do the most impactful things for you, you don't have to take all the advice, but it'd be great if you listen. And the stuff that has the most value, it'd be great if we actually tried it out. And again, we can do experiments. It doesn't have to be these big grand things. But if you come at it with that kind of mentality, I think you get the most out of people like us. And the other thing I'll offer is our perspectives are often very divergent from what you already have. And so it tends to have a lot of really interesting complementary perspectives. In many instances, you may have, like on your leadership team a lot of truly great lawyers who are just the most exquisite critical thinkers ever. But imagine if you brought somebody who was a systems thinker onto your bench and you let them really offer you perspective, that you might be amazed at the kind of complimentary outcomes that you get by just having a different type of thinker show up and having a real seat at the table. So, Mary, I wish I had a more linear response that was kind of rambled through cake and organs and other.

Things, but that was fantastic. That was such great advice. Confirms again, smartest guy in the room and one of my favorite people in this space. Jason, such a pleasure. Thank you for all the words of wisdom and thanks for being here today.

Thank you for letting me have the afternoon with you, Mary.