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EP 07: The Real Problem with In-House Legal Teams
9 Plays20 days ago
What does it take to succeed as a lawyer in a world shaped by AI, speed, and constant change?
Natalie Kim, VP of Legal at Omnidian, breaks down how modern in-house lawyers must go beyond legal expertise to think like operators. She shares her journey from Big Law to in-house, the shift toward building legal as a product, and the biggest inefficiencies holding legal teams back today.
The conversation also dives into AI’s growing impact on legal work—from automation and productivity gains to leadership challenges and trust in AI systems—along with practical advice on building a future-ready legal career.
Topics
Introduction: 00:00
Early interest in law, public policy, and problem-solving mindset: 01:41Law school expectations vs reality and desire for practical work: 03:53
Experiential learning through clinics and internships: 06:19
Big Law decision: training, constraints, and early career expectations: 09:40
Reality of Big Law: skill-building, pressure, and volume-driven learning: 12:21
Transition to in-house: timing, trade-offs, and unlearning law firm habits: 14:32
First in-house role at Cisco and becoming a generalist lawyer: 20:04
Building legal as a product: process, scalability, and long-term thinking: 25:44
The biggest problem in legal: inefficiency, context switching, and reactive work: 28:13
Why legal work becomes suboptimal: volume, accessibility, and manual processes: 31:39
AI and productivity: doing more vs doing better work: 36:56
AI adoption strategy: leadership, governance, and building the right foundation: 42:16
Will AI replace lawyers? Workstream shifts and new roles emerging: 45:29
Advice for law students and future career outlook in an AI-driven world: 53:13
Connect with us:
Natalie Kim - https://www.linkedin.com/in/nekim1/
Akshay Verma - https://www.linkedin.com/in/akshay-verma-esq/
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.
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Transcript
Introduction to Natalie Kim and Her Role
00:00:00
Speaker
I do think a lot, most of our day and definitely like more than 50% of it is spent in a suboptimal way. Right. And a lot of us will listening in might resonate with us, but my day is inundated with like slacks, emails, JIRA. And if I'm not intentional, I spend the whole day just reacting to whatever comes across my desk. yep and Because there's always too much to do and not enough time, right? And this can be for such wide ranging things, right? Like as VP Legal, sometimes I see like a high state contract. Sometimes I see like a new product feature that needs my sign off. Sometimes there's an employment question. And so when your scope is that broad and you're that overloaded, which I think describes most senior attorneys in-house, there's a huge amount of attention and context leakage.
00:00:58
Speaker
Hi everyone, am Akshay Verma, the host of Beacon Voices podcast and the COO at Spot Draft. Coming to you today from a very sunny and growing warm Northern Bay Area spring so spring afternoon. And really excited today to have a conversation with Natalie Kim, who is the VP of Legal at Omnidian. Natalie, thanks for joining me today. I'm really looking forward to kind of digging in on on some of the questions that we have around legal, legal tech, AI, and all things legal profession.
Natalie's Path to Law and Education
00:01:34
Speaker
Welcome to the podcast. Thank you so much to you and the Spot Draft community for having me. Good to be here. Absolutely. let's ah Let's dive right in. i often have many lawyers, but also legal professionals who've been in legal ops. You do a little bit of everything, which I think is really, really cool. But I'd love to start with like the inception of this journey for Natalie in the legal profession.
00:01:57
Speaker
You did your your undergrad work at Princeton, then went to Harvard Law. Tell us a little bit about why law school, was there anything in your time at Princeton that kind of said, hey, Natalie, you got to go to law school or is it something else?
00:02:11
Speaker
Sure. um So I guess going back in time, I was one of those kids who knew I wanted to be a lawyer early on. I didn't necessarily know what it was like day to day, but something about the kind of ethics of it. There were being a lot of like social justice, a lot of lawyers being involved in how to solve problems to make society better. I think that appealed to me as a kid. and In college, I majored in public policy, and I was really interested in how different societal forces, like in the realm of you know politics, society, culture, economics, history, like how all of that came together to inform how people decided to structure society and make lives better for people, which honestly is like what public policy is in a nutshell.
Law School Experiences and Practical Learning
00:02:58
Speaker
Yeah.
00:02:58
Speaker
And I'm also really very much a dabbler at heart. And so I love the fact that I could do a little bit of everything in this program instead of like taking 12 politics classes or 12 economics classes. I love that breadth of that program.
00:03:12
Speaker
And I think that led me to law school naturally as well. you know I just love to learn a little bit about everything. I think as a lawyer, you're constantly learning. And I think you hear this from a lot of different people, right? Like regardless of your area of law. And in in my case, it was technology, right? And so you have to keep up with technological developments. how that impacts regulation, but also how that impacts, you know, your clients that you serve, how that impacts your practice as well. And so I think this kind of constant treadmill or like the challenge of keeping up with the developments in the world around you, I think that really appealed to me in my choice to go to law school.
00:03:51
Speaker
Yeah. Did you have any expectations going into law school? What it was going to be like, what the practice of law was going to be like? I think I went in with like just like the visions that I saw on TV, to be honest you. I didn't really have any lawyers in my immediate community, like in my family or like family friends or anything like that. I think I had a vague sense that I would need to like ah read and like write really fast, which I had confidence in. But I think what surprised me about law school is just how litigation focused it was. Yeah.
00:04:21
Speaker
I knew early on, like that was not my cup of tea. i wanted to be close to the business. I wanted to do transactions. And so I found a lot of law school while like very informative and I had a lot of great professors and, you know, classmates to learn from. it was just not really relevant to the area of law that I wanted to practice. And so I think I spent a lot of law school just kind of raring to get out the gates. Like I can't wait to practice law. um And then, you know, i I found that I really enjoyed practicing law a lot more. Like I definitely had moments in law school where i was like, okay, is this going to be like the practice as well? Because I don't, I'm really interested in this.
00:05:02
Speaker
A little bit of crisis of faith moments for sure. yeah Yeah. Yeah. I think for all of us that went to law school and wanted to practice law and it wasn't, you know, it there were plenty of people in in my class as well who were kind of there because there wasn't anything better that they could think in terms of what to do
Transition to In-House Roles and Adaptation
00:05:20
Speaker
next. on elimination No judgment around that, but but it does change your approach. It changes your experience. It changes your expectations around what the experience in law school is going to be like, but also what it's like to be a lawyer.
00:05:31
Speaker
But I think when you go in with some level of intention like you did, then you seek out things that validate that intention to some extent. And so, you know, for me, is i'll I'll shoot this question over to you in a minute. um I really enjoyed the aspects of law school that allowed me to get my hands dirty where I wasn't just reading cases. Obviously, it's a huge skill set you have to do learn in law school. I wasn't just reading cases, but I was really applying the material in a way that was pseudo real, like semi real, right? Whether it was a moot court or trial team or something of that nature. And you're right. It's it's very heavily focused on litigation, motion practice, and and just that's the way you read. You read cases that.
00:06:14
Speaker
became litigation. So that's really kind of yeah the way that you started thinking about law school. But were there any specific experiences in law school that you can draw upon that you remember where you're like, this is what it will feel like to practice law. And I really like this.
00:06:27
Speaker
Yeah. Yeah. And so A couple of things bring to mind. I think one was the cyber law clinic and Harvard had a a bunch of different clinics, like some you know relating to criminal law and some relating to immigration law. And so the cyber law clinic um engaged on a pro bono basis, like startups and other technology companies trying to get their foot off the ground. and then usually it's um the population coming to the cyber law clinics are usually like solo founders who are very early on in their journey um they They don't have the money for like the Wilson Censini or like another firm. That's why they're kind of coming to this clinic. And I think it just gives you like a really broad based experience of like, OK, what is this founder needing help with? But maybe he doesn't know to bring up. right And so like it really tests your issue spotting skills and also trying to see around the corner for a client, which I found to be a really lasting, really useful skill set into my career. And so I think that was one experience.
00:07:32
Speaker
um I think definitely my internships during the summers. And so I spent my 1L year summer at Electronic Privacy Information Center, which is a nonprofit geared towards privacy rights based in DC. And that was a really amazing opportunity to kind of see more into the administrative workings of the federal government and like how you know FOIA requests work, like how um nonprofit parties get the information that they want from government agencies and you know how how slow grinding that that can be and like what challenges um ah are in those organizations' paths. And so I think those like brushes with real clients and real practicing lawyers and in all walks of life, like that really got me the exposure to what the practice was going to be like. um And I think generally speaking, I found myself drawn to newer areas of law where you know we didn't have centuries of precedent and lawyers and ah businesses alike were just trying to find figure out, OK, what do we do now that this new technology has hit us? There's no regulation that is really on point, but we need to keep moving. And so what do we do in the interim?
00:08:41
Speaker
And those are the questions that interested me. I think you know taking a look at kind of the availability of that experiential learning through law school, which I think is its increasing now. I went to Santa Clara. They have an entire certificate in the JD that's dedicated to that because you generally learn theory and you learn how to read cases and analyze them in law school. and that's not particularly helpful as you actually start practicing law. You have to learn how to file a motion. forget Forget about writing the motion. You have to learn how to file it. You have to learn how to sit down with a new client, your entrepreneur clinic experience. Sit down with a new client, build that relationship, build that rapport, build that trust, and then really try to understand what are their goals and how can I, through my knowledge of the law and the application of what this person is telling me in front of me right now, how can I make that successful for them? It's a huge jump from reading cases and in textbooks.
00:09:39
Speaker
um So you leave law school and and you decide to go to big law. You spend some time at Wilson. You spend some time at Kirkland. Tell us a little bit about, you know, what was the decision like that? Was it an easy decision? Was it the only path? It's a very different reality now for for law students, which i think is great. There's so much more opportunity. But for you coming out of law school, was that an intentional design where you where you said, I do want to go to ah ah a big firm for a little while? And and was there a rationale behind that?
00:10:09
Speaker
um I think it was a mixture of like available options at the time and then like wanting to get the training that a large law firm environment provided. And so, you know, like in law schools, ah especially at Harvard, it's very much an echo chamber. I think something like 75% of the graduating class went to a large law firm. And so it's not like, do you want to go to a large law firm? It's like, which big law firm are you going to go to? And it can very much feel like that is the only path and you're very much deviating from it if you consider a different path and so that that was very prevalent throughout campus um and i guess another thing that i had to take into account as an international student was like visa sponsorships right and yeah the landscape's changed a lot since then but at that point you know in large law firms were the only ones sponsoring hmp visas and so that really informed my path path decisioning as well. But there are also, you know, aspects to large law firms that really drew me from like a training perspective. Like um I like that the pathway was more standardized in a way that I can rely upon getting ah a consistent degree of training, working with the largest companies and like really high stakes deals. I think it puts you in the same rooms as like, you know, the highest, uh, uh,
00:11:28
Speaker
like the the the most um expertise and uh you know the highest quality kind of um practice that you're going to see in your practice area and so um being in the same rooms as those practitioners learning from them i think that was like a huge opportunity that stood out to me um and that did end up being the case in my three years at large law firms and like um Nowhere else really can you kind of come out straight out of the gate. You have no other job experience. I was KJD. This is my first job out of school.
00:11:59
Speaker
And you're sitting with CEOs, right? You're sitting with GCs and you're kind of learning secondhand through how these people make decisions. And so I think that was a tremendous opportunity in retrospect. Although I would say like it was ah it was a tough job like at the time. Like I won't lie about the, you know, the work-life balance challenges and all of that. But I think retrospectively, it was a tremendous opportunity to get that training.
00:12:20
Speaker
Yeah. and And again, I'll ask the same question asked about law school. Did you have an expectation of what that world was going to be like in the law firm before you went and did it kind of match up to what you what you had expected?
00:12:32
Speaker
I think so. I think so. like um I knew coming out of the gate that I wanted to handle transactional law. And you know like as I've talked about earlier on, I'm a dabbler. I like doing a little bit of everything. Wilson Sincini's corporate group is great in the sense that they gave junior associates a chance to take rotations. And so I did a stint at the Soma office at the time. They had a startup group.
00:12:54
Speaker
I did a stint in the SF offices M&A group. And so doing you know the whole gamut of transactions um that startup companies go through in their various stages of growth like really starting from you know like the two guys in a garage trope all the way up to you know public companies and so i think that gave me like that breadth that i was looking for um and i think it was also really great uh to just see in terms of sheer volume right like how these and it really feeds muscle memory right like it's not great if you're like up at 2 a.m. multiple nights in a row, like it's yeah, that's, that's a given, but in terms of the sheer amount of volume, you do gain a muscle memory for how you react in situations, especially high pressure situations, especially situations that require like a quick judgment. And so I do think that, um, that was the expectation that I had going in. Like i was pretty wider wide wide eyed about that. And then
00:13:50
Speaker
um Yeah, like the three years kind of delivered on that account. I was able to get that kind of breadth of corporate experience that has helped me in in-house roles since that time.
In-House Experiences at Cisco and Apple
00:13:58
Speaker
Yeah. you Look, generally speaking, three years at a law firm would be considered insufficient to be able to make the jump to the in-house role. Now, again, I i say that.
00:14:11
Speaker
through the lens of someone who's been in the legal profession for 26 years, graduated from law school 20 years ago, almost now, ah where to your earlier point, it was the really, the only path. If you wanted to do anything with your life as a lawyer, you were going to a law firm, small, medium, large, doesn't matter. be You were going to a law firm to get that training. um And, and so Three years and in the message back then was you got to spend six, seven, eight years at a law firm before an in-house role will take a look at you and take you seriously. um
00:14:44
Speaker
You managed to make the jump and we'll talk a little bit about your in-house career and how it unfolded. But did you have that feeling? Like how did that transition go after just three years? Yeah. You know, I think there's like no, um, one size fits all answer. And then you have pros and cons leaving at the three years mark. You have pros and cons leaving at the seven year mark, because I do think like for one thing, you have to unlearn a lot of behavior and how you work, uh, in a law firm, because it just does not translate well to in-house practice. And we can talk more about this too. Oh yes, we will. Example is to look, for example, um, like thinking, ah
00:15:22
Speaker
thinking two steps ahead for the business. Like when when you're in a law firm, you close the deal, you're done, you move on to the next deal. But then like in-house, you're like, okay, well, the sloppy contract language, I have to live with it for the next two years because I'm getting questions from my team every every six weeks about it. And so I think it's that kind of mindset shift that you have to make.
00:15:42
Speaker
um And so I became a little bit of an in-house whisperer, like ah for my law firm colleagues wanting to kind of make the in-house jump at various stages of the careers on I've heard a lot of, you know, I think I'm leaving too late on the other side as well, like especially from folks who had stayed like seven, eight, nine years, yeah finding that, you know, their like big law experience, which is extensive and they have like a ton of expertise in that area is actually showing up as a liability in some of their job search conversations. And I've also, you know, equivalently had folks on the other side of the fence who are like, oh, I think I went in house tour. early. Like I haven't really had experience really quarterbacking a large deal. And so I think it's honestly, it's what you make of it. And in-house environments vary so much more than large law firms do. And so I think regardless of when you leave, it's on you to do that due diligence, right? Like if you're leaving, especially earlier on in your career, are you landing in an in-house role where you have a mentor? Maybe you can continue to grow in the ways that you want to. And then if you're leaving kind of when you're more senior in your career, are you leaving to a role that you can
00:16:52
Speaker
um you can kind of get pigeonholed or you want to continue to grow in like the ways that you want to. And so I think, you know, there's different calculus that comes in for yeah kind of senior and senior people making the jump, but it's a calculus that you have to do at a loss. Yeah. I always used to wonder like, where is this like seven, eight year timeframe came, come from? yeah It's not like it was based on data or anything like that. And I think where I've landed now,
00:17:17
Speaker
which is you And you use the word, a really important word, which is unlearn. Law firm lawyers often have to unlearn, whether you want to call them bad habits, but they have to unlearn certain habits that you build up in the law firm world that are not really productive in the in-house world. And they're very counterproductive, in fact. You can be too risk averse. You don't really know how to think about the business first. and You think about the legal issues first, not the business facts first. But I always just wonder, like why why is this like seven or eight year earmarked timeframe there to be able to leave? Because if you stay that long, you're digging in on those habits more and more and more. The message that I used to get a lot was, well, it takes you that long to be experienced enough as a lawyer to go in house.
00:18:02
Speaker
But if the reality is that you're building up all these habits that you, or many of them you have to unlearn to go in house, like it actually makes more sense that you would leave earlier from your law firm days to go in house and really learn what it's like to be a business lawyer rather than a law firm lawyer. So I think it's, ah I'm hoping that that entire dynamic changes for the better. Cause if you look at the last 10 years of data now, the largest hirer of lawyers on the planet in house departments,
00:18:32
Speaker
Yeah. yeah'll We'll talk a little bit about legal operations and how that function has exploded in the last five or six years, especially. but But you can go back even further and you can see the proliferation of the in-house department.
00:18:44
Speaker
And it's only as a concept, 40 plus years old. You know, the first in-house department was created by GE and the CEO of GE in the 70s called up. I think it was Sullivan and Cromwell was their biggest law firm. Went to the main partner there and says, I'm paying you all this money. Why don't you just come work for me?
00:19:01
Speaker
come work for me, you build out your team, and I'll give you stock, and we can just give you access to everything here, rather than you having to do phone calls and back then faxes and whatever else it was. Yeah. I was surprised to learn, and this was already after I had become an in-house lawyer, that many decades ago, in-house used to be seen as like, oh, you're going out to pasture, you can hack it. Didn't make it. was kind of seen as a less than career compared to law firms. And then,
00:19:29
Speaker
there there is a shift in perception as well as different roles being created over a time like for example like uh uh google created the production uh product council after um you know finding out that you know we have these software product launches that are coming out in regular cadences when we find that outside counsel don't have that in-depth business knowledge to be able to like give us that just-in-time tailored uh advice and so we need somebody to be specializing in this and then kind of became known as the product council, but before that, that was one thing. and so Absolutely. Absolutely right. All right. Well, look, let's talk a little bit about your illustrious in-house career. You've spent time at some very large companies. Cisco is massive. Apple is massive. You're now at a smaller series C company in Omnidian. Tell us a little bit about how that first in-house role came about. What was it like? How did you think about it? And then how have you thought about your career career trajectory through the other roles?
00:20:26
Speaker
Yeah, I think people are surprised when I say I just applied through LinkedIn, did an interview and got a role, especially in this day and age, people are who gets roles that way anymore? But I did um And I really credit the Cisco legal team for training me to unlearn ah you know big law behaviors that have really helped me up until that point, and then learn a whole new set of behaviors that helped me in every single in-house role I've held since that time.
00:20:53
Speaker
And so, you know, ah when I joined Cisco, I was a corporate M&A lawyer. Corporate was all I knew. Like I did, you know, a little bit of tech trends, a little bit of employment as you have to like when you're quarterbacking an M&A in mini deal, but certainly was not a commercial lawyer by training. And so during my time at Cisco, I was able to retool in a way that I wanted to be like, I really wanted to be that generalist lawyer. I really wanted to kind of equip myself with that broad based skill set that would one day allow me to become a GC.
00:21:23
Speaker
um and so uh i was supporting a b2b sas product in the iot space i was their product council um i was uh running deals uh with telco companies all over the world like supporting a broad-based global sales team and then um doing privacy counseling as well like that's when i got the um CIPP certification as well. and And so I really had a tremendous time there, just like picking up all of these broad-based skill sets.
Leveraging Technology for Career Growth
00:21:55
Speaker
um
00:21:56
Speaker
And I learned a lot along the way. Like for example, like I think supporting sales is a very particular type of art that requires skills that maybe you don't experience in law firms. And I know the law firm nomenclature for it is like, you know, unsophisticated clients, I think is a little bit of word. But people who you interact with in law firms are like, you know, maybe they're like private equity or like experienced buyers of legal services. Whereas an in-house is not necessarily the case. Maybe you're the first lawyer that this person is ever speaking to working your entire life. And so a lot of like context switching, a lot of like tailoring my message to the audience. That's something that I had to pick up in my first in-house role as well.
00:22:42
Speaker
I think ah the further I get in my career, the shorter and more simple my emails become. And yes i definitely pride to myself in writing like, you know, really well thought out memo type emails, you know, five paragraphs. But um yeah, like those don't get read. So um I think just kind of adjusting to the in-house world was like the kind of biggest learning that I had in my first in-house role. um And then ah my I spent a brief stint at Apple supporting their App Store team. And that was another like great opportunity to see, like, what does a large company like Apple, how do they ship major changes to their products? like um
00:23:26
Speaker
when you're the app store and so many so many players on the ecosystem rely on you know you being kind consistent with your policies and you kind of showing up on time with you know the events that you hold at WWDC. And then you know every terms of service update gets scrutinized by you know thousands and thousands of app developers. like I think that was another kind of high stakes ah atmosphere that was really useful to learn from. And so...
00:23:54
Speaker
um After that, I was at Intrinsic, which is Alphabet's physical AI subsidiary. It has now been folded back into Google. But at the time, um it was a standalone subsidiary. I was their second lawyer hired. And then I stood up their commercial and privacy legal functions. And so that was really a fantastic learning in terms of, okay, how do we clear the jungle? Like, we do not have a contract in process yeah at all. yeah like We didn't have a CLM at all. How do we get from, oh our contracts are all over the place to, okay, let's put it on a Google Drive. like What is the type of review that I would like to instill in people's various contracts when they're coming from a starting point where, like okay, well, maybe these don't get reviewed or like
00:24:41
Speaker
ah there is no like existing process for it. And so um I think that really helped me run the exercise of like, what is an acceptable process development now that is going to help these folks? um Maybe it's not perfect, but like what is acceptable in the first year of the startup compared to the second year of the startup? And so kind of long range road mapping in a way that maybe you would ship a product for that was like a new way that I had thought of um in terms of ah running a legal department, like rather than looking at things as a discrete service item that's on your inbox.
00:25:20
Speaker
yeah um How can I look at legal as more of a product that I'm shipping that is like a little bit better every single quarter? And we have some kind of long term vision for it. And so, you know, plenty of legal teams kind of run like that. But I think it was the first time that I had made the mindset shift of like, I'm not just trying to get stuff off my desk. I'm trying to be build something. And did something or did somebody kind of impress upon you that that was necessary? Is that just something you picked up on in terms of I know our outcomes will be better if we did it this way? What was the genesis of that shift for you?
00:25:55
Speaker
I've definitely had managers who encouraged me to say like, okay, well, we're seeing a lot of the same problems. We never want to solve the same problem twice. And so how can we make sure that, you know, we create, you know, playbooks or self-service mechanisms But it's also the way I'm naturally wired, I feel like as well. um I really seek out inefficiency. I really seek out better ways of doing things. And if there is like new technology, i immediately get excited about it and see how we can leverage it to kind of
00:26:28
Speaker
um better my practice, like better my SLAs when it comes to showing up for my clients. And so I think I'm kind of naturally curious and wanting to find out, you know, ways to improve my practice. But there are definitely managers along the way who showed me that like, don't try and do things perfectly.
00:26:47
Speaker
don't or don't try and solve other people's problems for them too proactively. Because if you do that, then they don't have a chance to learn. And so I think kind of making that balance between like product appliance service versus letting some fires burn I think that was a learning that I've had along the way from good management. I was actually interviewed on a podcast a few weeks ago and somebody had asked me a very similar question around what was it about operations that really kind of drew you in? And, and you know, I've had the chance to kind of reflect on that over the last few years. and And there has always been this nagging feeling inside of me, like going back to even when I was a kid where like it if I didn't think that someone something was done in the proper way,
00:27:34
Speaker
I could not let it go. it yeah could not let it go. And to me, that is the foundation of what legal operations and efficiency creation and process of improvement are really all about. was like well, why do you do it that way? That doesn't make any sense. Like you spend all this time, you spend all this money, you're not you're still frustrated and you're not getting the outcomes that you, but you still continue to do that. Why do you continue to do it that way? So it'ss it's really nice and to to kind of share that thought with somebody who is still a practicing lawyer, but is so very operationally minded and has the genesis of that kind of feeling as well. um
00:28:13
Speaker
Here's a question I have. you've You've seen so many different kinds and sizes and complexities and sophistications of law departments. Here's a question for you about in-house law. What is the most broken thing in your perspective about how in-house lawyers do work?
00:28:30
Speaker
um And so here's where I might give you a hot take. Maybe you were aiming to ask this a little later, but I do think a lot, most of our day and definitely like more than 50% of it is spent in a suboptimal way,
AI's Role in Legal Operations
00:28:45
Speaker
right? And a lot of us small listening in might resonate with this, but my day is inundated with like slacks, emails, JIRA. And if I'm not intentional, I spend the whole day just reacting to whatever comes across my desk. yep and Because there's always too much to do and not enough time, right? And this can be for such wide ranging things, right? Like as BP Legal, sometimes I see like a high state contract. Sometimes I see like a new product feature that needs my sign off. Sometimes there's an employment question. And so when your scope is that broad and you're that overloaded, which I think describes most senior attorneys in-house, there's a huge amount of attention and context leakage. right For example, say I'm working on this you know high attention heavy, high context workstream, say it's like a high dollar contract or litigation, there's this context loading I have to do before I add any value to that workstream.
00:29:42
Speaker
And during that workstream, I'm protecting myself from the constant onslaught of distractions, right? Like pings on three different apps. um And unfortunately, you know, like these intake platforms, they don't differentiate, right? They all look like, you know, bolded lines on a page on a dashboard and then You can't find out how important they are until you click on it and find out. So it's kind of like playing Russian roulette with your attention. And so by the time you you know you get out of this other meeting, you have to context load it again. yeah There's also this you know bucket of time that you're spending answering questions that can be automated, right increasingly so. right Like, yeah hey, where do i find this article? Or like what is the answer to this question that's already in a playbook? And I used to think, you know this is all part and parcel of work. This is all part and parcel of client service. but I think especially in this age of AI where a lot of this can be automated away, like the client can get the answer quicker than me getting to it after digging manually. um
00:30:39
Speaker
i think that that is something that we can think about deploying our attention and judgment more intentionally on. And so if you're spending most of your day doing that firefighting, then you're spending it in a spotable way.
00:30:53
Speaker
Yeah, this to me is the foundational goal. The holy grail of legal operations is to help the legal department and the lawyers spend more and more and more of their time on their what we call call it whatever. but I like to call it core strategic work. it's It's the reason you were hired. It's the reason most likely that you took the job. It's the reason that really drives you as a lawyer and to some extent as a human being to really help counsel strategically your clients and your customers in-house. And yet there is this operational drag, for lack of a better term, that continues to bring in-house departments and in-house lawyers down. um
00:31:39
Speaker
Why do you think that drag was created in the first place? Let's say even before um before Slack and before all these apps were pinging us and maybe not before email, but but to some extent, before the technology increased the volume of distraction, was there anything about in-house law or running the business or lawyers that you think really kind of lended itself to creating this kind of a situation?
00:32:06
Speaker
Oh, absolutely. i think, um and you've touched on this a little bit in your question, like with more technology, the pace gets faster and the volume can increase, right? Like before we had email, we were ferrying stuff by courier from office. We had to wait until that courier like arrived, right? like yeah So pace gets quicker.
00:32:28
Speaker
And so that's why I always laugh when people are like, oh, you know, with this new technology, people will be working like 10 hour a weeks. Everything will be great. We're all going to be on the beach. and like No, we're just going to be shipping more per hour of work. Yes. um But i do think, you know, like the fact that You're billing, i don't even know what the hourly rate is anymore, but it was 600 when I was a first year associate.
00:32:48
Speaker
okay the fact that you and noting four thousand you yeah like it's inside yeah not even keep up but The fact that you're not paying your lawyer, six hundred an hour I think that that does two things. One is a good thing, one is a bad thing. One is that they're more approachable. You can go to them early with things that maybe might become a legal question later. You can fill them in earlier, give them context, um give them the chance to influence the decision in a positive way. And so I think that that's good. That you know leads to more emails and more touch points. But I think ultimately that is a good thing.
00:33:21
Speaker
um But it also leads to like sloppy questions or like things that, you know, maybe are available somewhere if you click three times, but, you know, emailing Natalie is a lot easier. And so I think it does lend itself to more volume of that kind of ah lower and middle risk layer of intake questions that come in.
00:33:43
Speaker
Yeah. Yeah, when you add to that, i but fully agree, when you add to that, the manual nature in which most people do their work, forget about the legal profession, but just everywhere, the manual nature in which people do their work, even if automation is available, we tend to do it that way for some human reason that I probably haven't quite put my finger on.
00:34:05
Speaker
At scale, and then you've been at some very large places, at scale, that's going to drag you down. It's going to massive manual task drag that will continue to bring things to a a grinding halt. And it's really difficult at scale to get out of some of those things. You've done product development, you've done commercial work, you've done all this. So you've seen the different verticals with within which you can create that kind of a drag. And I think you know we don't talk about these things in law school. We don't talk about technology. We don't talk about data. but We don't learn about efficiency or process or any of those kinds of things. Those are generally business drivers and business outcomes and business skill sets. mary I've never gone to business school, so I'm not sure if they teach those things in business school. But you cannot run and grow and build a good business without knowing those things at some capacity. And you you know you you had an inherent disposition and it's some inherent skill sets that kind of brought you to that. Others who come to the in-house world, they realize they really cannot succeed without picking up on some of those things. And so I think all of that kind of comes together. And now we'll talk little about legal operations and legal tech and in a little bit here. more specifically, but now in the age of AI,
00:35:26
Speaker
think there's a real opportunity, although I've said this before. I've said this i said this before in the age of you know flexible resource staffing with outside counsel displacement. And I said this in the age of other non-AI legal technology really growing you know in the 2016, 2017 era. And now with AI, I'm saying it again.
00:35:46
Speaker
But um there's an interesting data set that is coming up in AI. and And I want to talk about that as kind of the inception because you just touched on this. The anticipation was that if we're using AI, then we're making our lives easier. We're doing things faster. I'll just use contract redlining because I think every lawyer really understands what that means.
00:36:06
Speaker
If I have a point solution, that allows me to redline my contracts faster. So it's got a playbook boltit built in, it uses generative AI, it gives me suggested language for whatever it is that's in front of me. And let's say it reduces my review time for that contract down from, you know, two hours to 15 minutes. That is significant. It is a significant reduction.
00:36:28
Speaker
And let's say before that, I was getting through 10 contracts in a day. Now with that, you do the math, it won't be right, but now I can get through 30 or 35 or 40, whatever it is, contracts in a day. What does my baseline then become?
00:36:40
Speaker
What does my baseline then become? Because that is the nature of capitalism and it's the nature of lawyers because we really tie our identities to working hard. And so now you're seeing that, and this is this is actual data that's being put out there with AI, people are spending more time doing work and I'm removing from that Whatever change management time there may be involved in learning new technology and building it into your own personal process to do things, let's remove that from the equation. People are just doing more work now because that's sort of where does that end? Does it end? How does it end? What are your thoughts on that? said Somewhat a philosophical question, but I'd love to get your take on that.
00:37:16
Speaker
Yeah, you know, I've been hearing this in my corner of LinkedIn, like the GC network that I'm in also in boardrooms as well. Like there's a lot of talk about like, okay, now that we have this technology, we have to raise the bar, both in terms of output, like productivity, as well as performance, right? And so um i think I've read somewhere like AI fry is becoming a thing. Like if people use, and this talks about if people use AI a lot, they just feel more exhausted. and I think There are a few components there, right? Like say I have been able to review 10 contracts a day, but now because I have AI, I'm doing 30. I think I would still have that like lingering anxiety of like, is this right? Like, is the AI right? I am trusting the AI with some part of my work, whether it's like the review or analysis or like issue spotting, what have you, is this right? And so I think there's that like underlying question,
00:38:13
Speaker
um And there's also, you know, the fact that thinking is thinking is a stage of this exercise that you can kind of slow down and um and people join legal teams, they take on roles for different reasons, but you can kind of get into a state of flow and you cannot like get in and out of a state of flow in like two minute increments, you cannot. And so some some things just require that like you're getting into the zone, you're like in the zone, you ship the contract and that feeling of like accomplishment. I think that is a little bit,
00:38:47
Speaker
I don't want to say like threatened, but I think that changes a little bit. And it's like a change to how people have been working in the age of AI. Like, okay, it's the end of the day. I've shipped 35 contracts, but maybe I don't feel as good about it as I did before. And so I think that's a real thing that, you know, leaders and both team members have to grapple with.
00:39:06
Speaker
Yeah, i did so I think you nailed it right there. To me, at its core, this is a leadership and an organizational decision to make. Absolutely. You can't answer Every exec, every GC, CLO, I think I would find a hard time believing that anyone would deny that if we are freeing up time for ourselves by leveraging technology,
00:39:34
Speaker
that deploying that time back into the business in a core strategic manner rather than just more work. And I really see those two very differently. i think you can spend two hours doing deep thinking around your business unit or your function or your company. And to to some extent, and especially in the kinds of senior roles that we're in now, that can be far more valuable than doing 10 more contracts.
00:39:58
Speaker
Right, right. But it becomes a it becomes a leadership issue. How do i how do i disseminate that ethos through my team? how do i How do I create intention that people, when they have that time, they actually do it rather than just getting through more contracts? Because that's a very tangible outcome and and it feels, and to some extent, feels good that we get through it. I don't know. you Would you have any advice for executives or or senior leaders in legal to be able to create that for their teams? Yeah.
00:40:25
Speaker
Yeah, I think um absolutely. And this is very much something that you cannot outsource. like I see teams, I speak to team members who like, you know my GC isn't super into AI, but then there's this one guy who likes to tinker around and then all the AI thinking belongs to that one guy, or like, oh, it's a legal ops issue. right And so I think it really needs to start from the top, like this ethos of um what AI is in our legal team and The answer to that will depend on you know whether you're a venture backed company or like a healthcare plan. It's going to depend like where your risk calibrations are. But there needs to be some kind of like alignment in terms of this is how AI is going to be used in our team.
00:41:01
Speaker
um And this is how I expect you to spend the time that is freed up and in In my own team, we talk about high judgment and low judgment tasks and AI as a potential source of career growth. right like If you're clicking on five different things over and over, that's not a good use of your time. right like That's not a good use of your attention and judgment that we hired you for. and so Automate that.
00:41:25
Speaker
and With the time that is freed up, like make a judgment call in terms of, like do you want to spend more of that? and It's going to depend on the role. Do you want to spend more of that time like executing more or do you want to spend that time on like high judgment strategic work that, you know, get you promoted, like moves the needle for the company? And so I think making space for that as an executive, as a leader is really, really important.
00:41:49
Speaker
Yeah, I think it's ah it's it's a tough thing to do. It's a tough thing to do because it may not necessarily show up at the capitalistic way that we are so used to thinking about impact, which is dollar values or risk reduction or cost savings or whatever it may be.
Future of AI in Law and Career Advice
00:42:06
Speaker
But it does have, in my view, and I think yours as well, significant long-term implications for the organization and for the individual if you can if you can carve out some time to do that.
00:42:16
Speaker
Yeah. But we've started to touch on AI. I mean, obviously with with legal operations and you have that I spent six years at Facebook and Coinbase leading their ops teams, technology was a huge component of how legal operations would go about doing things. But one of the things that I will, I think, probably...
00:42:36
Speaker
to my grave espouse when it comes to technology or legal operations or creating efficiency is that if you don't think first about people in process and then apply technology, all you end up doing is either proliferating the pain that you were feeling that you were hoping the technology would solve or creating other issues altogether. Do you generally agree with that? And and can you share an example or two of where you've actually seen that play out in your own career?
00:43:04
Speaker
Yeah, absolutely. um so this is going to be a medium length story. When I joined my company, ah there was a lot of experimentation with technology and a bit of a vacuum where nobody was really kind of grappling with AI in a holistic way. And by holistic, I mean like people, process, governance and technology and having like a unified viewpoint that is informed by those things. And so the first thing I did after putting my hand up was running a survey. Like where rare is the landscape right now? asked people, how are you using ai
00:43:36
Speaker
um What problems do you see with our adoption so far? And basically what's getting in your way. And so yeah we consistently heard that there's a lack of unified guidance in terms of what's okay and what's not okay.
00:43:47
Speaker
And there's and not a lot of training opportunities. And that was really holding people back. And so we responded to that with a set of purpose-built governance frameworks. And so an AI policy, you know, like procurement processes specific to AI tools, responsible AI training, as well as prompt training, because we believe that like skills gain is all about, you know, you learn how to do the thing as well as how to do the thing in an ethical way that's like, you know, aligned with our values. And so I think We really had an emphasis on people and processes first, because you know you can't sprint in a jungle, right? Like you can sprint on a highway, but you cannot sprint on a jungle. And so like that we really wanted to give people clear guardrails, as well as unlock people from skills perspective. And then we also, and this I feel like was really crucial, we got the ELT, the leadership to sit down and really stare at like, who are we as as a company when it comes to AI, like in terms of how we incorporate AI into our OKRs, planning, like resourcing, like how do we think about that? What are our expectations for our employees when it comes to AI? Because, you know, there there's a lot of different answers. And the answer has to align with your culture. If you want to be able to say it 77 times with a straight face in front of various audiences, like in front your employees, in front of your board, right? It all needs to kind of come together in a cogent way. And so, and then only after that came major technology transformations. And so in the last six months, we've seen like meaningful upticks in both AI adoption as well as sentiment towards AI. And so I think we really kind of built a sense of clarity and like who we are as a company when it comes to AI, kind of before you know having people off their races building.
00:45:28
Speaker
Yeah. um So let's talk about some of the um issues kind of surrounding AI and how our profession is thinking about them. And let's let's take one head on that I think has been a little bit of a narrative, not just for our profession, but you're seeing it everywhere now, particularly with ah you know the large language models starting to kind of go into the legal workspace a little bit here and there.
00:45:51
Speaker
Do you see AI replacing lawyers anywhere down the road? Yeah. um That is a really good question. i wish I had the crystal ball here, but I know what's in vogue nowadays is people say like, oh, you know, AI is not going to replace lawyers.
00:46:07
Speaker
It's only going to replace lawyers not using AI. And so you bet you better get started using AI. I do think that AI is actually going to replace entire legal work streams at some point. like Don't ask me like when that's going happen. yeah But things like due diligence, for example, like playbook based, low risk type contracting, maybe it just won't exist in the way that it's existed for yes previous decades. But, and this is where I kind of diverge from the, I don't know if there's a consensus here, but from from a lot of the stuff that I see around me is, I do think there's going to be new work streams that are created. Because if I learned anything from my time in Silicon Valley in Seattle, it's like more technology, more problems, right? And so there's going to be new roles. For example, I'm seeing people hired in as chief legal architect in some legal tech companies. And
00:47:01
Speaker
ah there's going to be this massive need for agentic AI orchestration, right? Like making sure that these agents that, you know, your team is building a mile a minute, they're all like orchestrated together, doing your bidding in a way that is consistent with, you know values, risk calibration of the business, and then really treating it as a life cycle, right? And so I think you're going to see a lot of growth in that area and obviously a lot of stuff that we don't even foresee happening right now. And so I think it's just going to be a shift in terms of work streams that have existed going away, but new new work streams coming to pass.
00:47:38
Speaker
Now, shifting focus a little bit within AI and kind of outputs and trust and so forth. How do you balance, how do you personally balance trust and AI outputs with accountability when legal ultimately owns the risk call?
00:47:51
Speaker
Yeah, yeah. And I think it's worth spending a little bit of time on like the extremes. We all want to be in the happy middle, but like there is also there is also a trusting AI to little, right? like There are some teams that are like, I double check everything that AI generates.
00:48:10
Speaker
And I don't think that's really using AI to get that efficiency and productivity gain if you trust it so little that you're essentially replicating the entire work. And obviously, you know, there's the other extreme where, you know, you trust it too much and you're reckless with it and bad things happen that we have all seen the headlines about.
00:48:26
Speaker
um I like to break it down into like risk as well as like different subtasks. And so I tend to trust AI more when it comes to analysis that I can double check or like reading through this long thing and getting me that needle in a haystack. And so, for example, if I need to make some kind of corporate legal call, on something that ah depends on some kind of finding that's in our board materials, um I would ask AI to look at that. I would not spend time going through five years of board materials, right?
00:49:00
Speaker
But then in terms of making that strategic call, like that part, I would not outsource to AI. And I don't foresee doing that for a time. And so i think um if you bucket it into this is low, medium, high stakes, that's a good starting point, but it's incomplete because even in the high stakes work streams, there are lower stakes and more easily verifiable sub tasks that you can delegate effectively to AI. And so that's kind of how we think about it in our team. Yeah. and But I also think you illustrated what I think is the bifurcation of things that i think have been lumped together for far too long.
00:49:36
Speaker
I would say when it comes to something like due diligence for an M&A transaction or some other kind of corporate transaction, The due diligence part is not really legal work. I know legal has to give the stamp on it at the end of the day, but that is high volume review work. There's no legal judgment that's really required. right We saw eDiscovery go in this direction with technology assisted review 20 years ago.
00:50:00
Speaker
maybe 15 years ago. So we've had that machine learning capability available to us with large amounts of data that give us an output, but then ultimately requires legal judgment in order to be able to verify, tweak, or whatever it is that you need to to do with that output. To me, that's the quintessential need for the lawyer.
00:50:16
Speaker
You are applying your legal training and your legal judgment. I think the problem has been that we have lumped everything together. And before it was with law firms, literally law firms were at the top of the food chain for legal services delivery, because once you gain a little bit of trust with one organization to do this work, and let's say that was super high stakes, very high percentage level of legal judgment involved. Once you give that to somebody and you start trusting them, you just start giving them more and more in work. And then all of a sudden they're taking a mountain of work. But so much of the work that even law firms are doing
00:50:48
Speaker
and you saw this taken away from them over time they were doing e-discovery and litigation they were had they had mountains of associates and mountains of documents that they were going through i used to do that as a paralegal uh and that we i used to be at latham so they would do that work that has now shifted almost entirely to legal services providers alsps legal technology vendors and so forth so i think we'll continue to see that bifurcation and that and that unbundling of work which will get lawyers back to what they really, really enjoy doing, which is that core strategic work, whether they are at the law firm or they are in-house. What that means for the economies
00:51:25
Speaker
of those two types of organizations, I am not going to say here because it yeah doesn't sound great. right you're You're losing revenue. You're using those kinds of things. But I do think that in the long run, without some short-term pain, you can't have that long-term stability. I do think in the long term, it bodes really well for lawyers and for those organizations and for the profession itself.
00:51:45
Speaker
we'll see it's Yeah, would agree with that. For example, I think you hit the nail on the head with e-discovery. The corporate equivalent of that is due diligence. And i I love how the conversation has shifted in terms of ai accuracy, because it used to be that, oh, you're 98% accurate. We can't use you because you're not 100%. And then we started to compare actually with humans perform the same task, because humans aren't 100% accurate. And so we've actually seen that a lot of these AI platforms are more accurate than humans perform the same task. And that was always the lingering thought in my head when I was a junior associate looking at 500 contracts. Let me try and find a determination provision and summarize them manually into an Excel. at It's always like an ungodly hour, right? And so I always had this fear of like, what if I miss something? What if I'm wrong? The answer was, I probably was, right? And so if we can get this done quicker, more efficiently, and maybe even more accurately with AI, like that is something that we can kind of peel off.
00:52:42
Speaker
Yeah. I'm sure we could do an an all an entire other episode around how malpractice insurance would have covered you had you missed something. But now, like, what is, mean, to me, you know, and again, I'm not an insurance provider, but it feels pretty straightforward to start applying that to any technology that a a user would be using in the same kind of fashion. Like, why should that change? Yes, I know it's not a human doing the work, but but I don't see that being a huge hurdle to to kind of evolving in that from ah just from an insurance perspective. Okay.
00:53:13
Speaker
I have three questions that I ask every single guest. They're a little bit backward looking and a little bit forward looking. Okay. So this is the first question. What advice, thinking back with the benefit of hindsight, by the way, what advice would you give your law school self?
00:53:30
Speaker
Other than like which specific stock to buy, ah i i would I would just say increase your appetite or your aperture for possible change. right like And when I was in law school, it just seemed really immutable. like you know The vault rankings determine you know what is the the best career, like what is how you are successful, how to get there. And so the world has changed so much like in the time that I've been practicing. And in the grand scheme of things, it's a long long period of time. um
00:54:05
Speaker
we had like a global pandemic, we had AI upend just how we, how we practice, how lawyers make money. And so, so much has changed in the professional front. And then I guess also don't underestimate how like your personal outlook can change, like as your life, as, as you age and have kind of more life milestones, right? Like I've had three kids and and that's changed, know, how I look at jobs, like how I look at my career and also my tolerance for like various BS. And so it's a lot. And I think being over 10 years in, I see friends who have taken radically different paths, right, like both inside and outside law. And so I would just say to myself, expect change and cultivate genuine interests that can survive that.
00:54:51
Speaker
Yeah, great advice. Okay, shifting focus to law students today. So let's say we're coming up on May. May is generally and universally in this country graduation time for law students.
00:55:04
Speaker
um Would the advice that you just gave to your law school self, would it change for current law students at all? And if so, how? Hmm. I think I want to first start by acknowledging that this is not like a plain vanilla time to be graduating from school. Like there is just a lot of changes, right? Like AI is a thing, but also like there's a lot of layoffs, right? There's a lot of feelings of uncertainty about um coming into the workforce. And so um i think for specifically the crop of folks graduating this year, i would say um so one one's very specific to AI, one's kind of more general. um I would say dive deep into AI, become a power user. And this doesn't have to be because you want to be using AI daily at work for whatever role that you're in, but I think it really helps from like a horizon perspective beyond you know differentiating yourself from a job candidate perspective. um And then the second piece of advice I would say is just kind of sit and think to yourself, like, where do I see the market going? Where do I see the industry panning out in the next while? And and I felt this at the time, and maybe a lot of younger folks would feel this way, like, oh, I don't know, first of all, like, how am I supposed to pay this out? But then, you know, you're making a bet whether you know it or not, right? Like, do you think it'll be like the large law firms that handle this transition the best? Is it going to be a legal tech company, an in-house company? Like, you, you
00:56:27
Speaker
make a bet by taking a job, right? Like every job is a paycheck, but it's also an investment of your time, which will pay dividends in terms of career growth and in terms of like your subsequent opportunities available to you. And so I would say like choose intentionally, like don't be on autopilot.
00:56:45
Speaker
um I think the central advice that I would have given to myself does not change, but I think, especially for folks graduating now, like, okay, look at AI. Like I know everybody's talking about AI all the time, but spend some time on it. Like go along your own learning journey there.
00:57:01
Speaker
Yeah. Great advice. All right. Last question. um If you have the luxury of thinking 10 years ahead, and I don't know if we do or not, because so much can be different. So if you want to make this five years, that's absolutely fine. But what path do you hope you've taken personally? Where do you hope to be?
00:57:18
Speaker
Yeah, great question. I usually think only about 24 hours ahead. And so this is more than a parent of three. That makes a lot of sense, to be honest. Yeah. um You know, actually, i would say, like, I would love to continue leveraging the work that I've done on AI acceleration and governance at my current company. It's been a great opportunity just because you can, I feel like I've off-roaded so much from what typical lawyers do. And that's just been such a fun and rewarding experience. And so I would love to continue to work with boards of management to have greater impact in terms of how to utilize AI in an effective way, but also in a responsible way. Um, and all the conversations I'm having with people in the industry, there's so many teams who are just not grappling with the questions in the right way or they're not really ready for the transitions. And so I've always thought about like you know next chapter, like whatever is the next step in my career as like what is this vacuum that nobody's stepping into or there isn't a ready answer? that I can dive into and and learn a lot along the way. And so far, that's been like a really rewarding strategy. And so i'll probably continue to do that.
00:58:27
Speaker
I think it'll pay off dividends massively. I think it's a great way to look at your career. My guest today has been Natalie Kim, VP of Legal at Omnidian. She shared some great insights on what makes for success on the in-house world, how to think about AI, what AI may hold for lawyers, our profession and the world in the future, and some great advice for law students. Natalie, thank you so much for joining us today. It was a really fun conversation.
00:58:52
Speaker
Thank you for having me.