What Modern Legal Leaders Get Wrong About AI

Tonkean: Welcome to Modern Business Operations, where we talk with leaders about how ops is

Jasmine: adapting to our modern world.

Tonkean: Hello everyone. Welcome to another episode of Modern Business Operations. Today I have the pleasure of hosting Jasmin. Thank you for joining me, Jasmine.

Jasmine: Thank you so much for having me. I'm excited to be here.

Tonkean: Well, Jasmine is a general consulate, IonCloud, which is an exciting company if you don't know about them. But part of this, you are also at Binti and Patreon, Pinterest, a lot of interesting, uh, companies. So maybe we start there. Maybe you can share a little bit about your journey, uh, and what you guys are doing today and maybe as well. And uh, yeah, we can start there.

Jasmine: Yeah, sure. So I tend to find that it helps me to go forward, progression in my career arc because it explains some of how I got to where I am. So I started in San Francisco in big law firms, uh, doing complex commercial litigation. So a little bit of everything on the litigation side. And I went to three different firms and over the course of those firms sort of had a realization that two things were happening for me. One is I was never satisfied. I felt like I was looking for something and I couldn't find it. And I just kept thinking, maybe if I go to the next place I will find it. And that did not ring to be true. So that was one, uh, error in my thinking. But the, the second thing that kept happening is I kept feeling like I was not aligning with my values, my goals, my ambitions. I felt like I a, I wasn't living up to my potential because oftentimes I was just in a closed office, you know, doing quiet work, which I felt like was not really my life's calling. But the second thing was I felt like I was not values aligned doing work that I was passionate about. And I actually started to think that I wasn't a very good lawyer because I wasn't always very satisfied with the practice of law. And I was, you know, like most big law folks, burnt out, exhausted, you know, not having the best career experience, uh, I, I think I possibly could have. And so after a pretty particularly rough go, I decided to take a break and I quit my job altogether. And I had no plan, really. I just knew that I something needed to shift. And so long as I was working until 4 o' clock in the morning every day, nothing was going to change. Right. I just knew that I would keep doing that. So dramatic turn left. My husband, who was my fiance at the time, was living in Las Vegas. I put all of my stuff in storage. And I drove my car from San Francisco to Las Vegas, and I sat on his couch and I said, oh, my gosh, what have I done? What am I gonna do with my life, my career? I can't believe I just made that decision. It was this moment where I was like, I can't believe that happened. And now what do I do? And so I started to think, for the first time actually in my entire life, I thought, what do I actually want to do? Who do I want to be? Not just what do I have to do? What's the gold star? What's the most achieving, you know, high success thing I can do to make my parents proud or, you know, tick some stuff, some achievement off of my list. And so I just started making lists of, like, things I thought I was good at and things that I thought were fun. And one thing has been true my entire life is that I love health, wellness, fitness. I grew up playing sports. I've always been a part of a team. And so I thought to myself, okay, I'm going to go become a fitness instructor. And so I did. I actually trained at a studio in Las Vegas, and I became an indoor cycling studio. And it was, at that time, the best job I had ever had. And I tell people that resoundingly to this day, ah, the reason it was the best job I'd had was one, I was making a real difference. And I saw that difference every day. I saw it in the smiles, um, that people brought to my classes. I saw it in their fake use to me. I saw it in the difference that I felt like I was making in their day. And I felt like I was part of a team. Like, I was actually working towards something with a group of people. And so right about now, you might be thinking to yourself, like, are you going to talk about your job or not? Uh, but the reason this was so pivotal for me is because it showed me how to go and get a job. That gave me that sense of satisfaction, that gave me that sense of purpose. And so, you know, for a while, I was convinced I had ruined my career. There was no turning back for me. Maybe I was just going to never be a lawyer again, but, you know, the high achiever in me was not going to go quietly into the night. And so I pushed really hard to try to find a job in house because I thought that that would give me a chance to build and be a part of a team the way that I wanted to. And I decided I would not be a litigator anymore, that I would try to do transactional work specifically again because I liked the communal aspect of it, the deal making, et cetera. So I uh, my first in house job very fittingly was at 24 Hour Fitness which was a nice connection to the fitness mission. And I uh, that was the first place I helped to implement a clm and it gave me exposure to process scale, you know, global commercial work. And from there I went to Pinterest where I started as the first and only commercial lawyer dedicated to doing commercial work. I implemented Ironclad for the first time. I grew my team over time and you know, I loved my time at Pinterest and over the course of almost four years decided that I knew I wanted to do more than just commercial work. So then I left and I went to Patreon and I led both the intellectual property and the commercial teams as deputy GC there. And I was only there for a short period of time before my first GC job came knocking. And that was Binti, which is an early stage SaaS company that made software for social uh, welfare. So we, we helped with foster an adoptive care process which was my fourth ven CLM installation was at that company. And then I came to Ironclad just about a year ago. And what's really interesting about my Binti to Ironclad Trans is that at the end of the day BITI also was a uh, workflow automation tool. It was a digitization of an application, not a contract. Right. But working through a workflow ultimately with role based access and permissions and then storage in a repository. So there was a really nice parallel into the job at Ironclad. And because I had implemented Ironclad twice before, I was really passionate about the project uh, and the product and all of our company's potential. So it's been about a year now and it's been amazing.

Tonkean: Well, congratulations. First of all, I love the, I love the twist and turn of this story. It's amazing. I think a lot of people are struggling with that moment that you described pretty well. Like, you know, is that, is that what I want to do? And I think you did two things that I think people can take away. And, and honestly it's better for everyone. Like it's better for their personal life, like emotional life, like the way their professional life, their employers honestly, you know, would appreciate it. Um, at the end of the day you want to work with and you want to have people that are enjoying what they're doing and they're, you know, and filling it. So, so the first Thing is jumping is making the change, so that's good for that. But I really like the way you describe the, the list of things you're good at and the things you like to do.

Speaker C: Yeah.

Tonkean: And we've seen a lot of changes in, in the, in the, in the workforce, you know, in the last few years. How, how do you feel that affected, you know, those few. Because you went through all of it. And if I did my math correctly, then came Covid, and now, like recently with all the AI, boom, like, how do you feel like this have, uh, changed from the timing you kind of joined the tech side of the house, if you will.

Jasmine: Yeah, I have seen so much change. A transition of the tech side of the house that's starting, uh, in the industry, I mean, between Covid and AI and you know, the hypergrowth period of SAS in general preceding AI, it has just been so much change and iteration. And I think as a lawyer, it's really interesting because what we're trained to do actually is learn. And so especially as litigators. Right. And so the fundamentals of what I learned in law school and then honed at, uh, my early days at a law firm, I am now seeing just how valuable all of that is because, you know, every transition is an opportunity for me to learn something new, whether it's changing course of the business, changing pace, new technology, whatever that might be. And so I'm actually finding that a lot of those legacy experiences that I amassed are now particularly useful because what I could do is get up to speed pretty quickly, um, on whatever it is that's happening and know that I have that resilience and ability in a way that I think is really unique and fascinating in the tech world, but also helping my peers and my partners navigate that instability. Right. Because oftentimes lawyers have to be the voice of reason. Right. When there is a fire, when there is an emergency, we are the ones running towards that emergency to try to help and try to solve, not the ones running away. And so, um, also that training, in terms of all of the chaos, for lack of a better word, sometimes of, you know, being an attorney, that, that really does help us navigate just better. A, uh, little bit better anyway, all of the changes that we've been going through. And I think, you know, that's, uh, it might be one of the reasons why lawyers are adopting AI right now so quickly. For example, Ted, you hear this adage that like, oh, the legal world is the last one to revolutionize, uh, its technology. We're slow adopters, but if you look at the adoption rates, legal AI and legal adopters of AI are astronomical. Right. And I think some of it is because A, we're all yearning for change, I think that's true. B, we're all trying to keep up with a really fast pace in business and the acceleration that's happening there. C, I think that we love learning and this is a brand new technology and something that is an opportunity for all of us to go and explore and conquer a bit. So I think that combination is creating a really fun moment right now in the practice.

Tonkean: Yeah, I really do. I wanted to bring it up. It's really true. It's, it's quite phenomenal to see. You know, even when you look at the last year, forget about the last, you know, two and a half years, just in the past 12 months, it feels like the legal, uh, the AI adoption legal is ahead of every other department by a mile. And there's a lot of people talking about a lot of things, but where it's actually, you know, companies live with it. How do you think the different sizes also like, I think companies you mentioned you've worked for different sizes, different stage, where, um, were you to create this team again in two years, three years, five years, how different do you feel like this would be? Not only, not theoretically, because everyone can kind of feel it will be different, but like, do you have practical areas where you'll be like, honestly, I don't know if we would do this type of work like that anymore.

Jasmine: I don't know that there is any work we wouldn't staff the same way because we are already a, uh, fiddly resource type of growth. You know, I think most folks that are my peers at companies, um, think about it the same way. But I think what we might do is think about our approach to outside council just a little bit differently. How we reduce our spend on outside counsel, how we increase our pace of work and efficiency, how we think about outsourcing, uh, for lack of a better word, certain of the rote work to AI. So it doesn't necessarily change how I staff or resource certain work, but it does change how we execute on that work. And frankly, I think that execution has to do with the sustainability of performance at that high of a level because lawyers are held to the highest standards. Like we can't be imperfect on certain work, right. Other, other work, you have to make risk, reward, trade offs and you do your best. But by and large we have to do things in accordance with a standard of care. That's our Ethical obligation. Right. And so it can feel very daunting to some because you're so afraid to make a mistake. It can also feel very intimidating because you have to apply that same level of rigor to everything you do. And so I think the advent of AI what it does is it gives all of us a first pass at so much of the rote work that we maybe didn't want to do in the first place. The drudgery a little bit, right? Where we're like, oh my gosh, it's no longer a blank piece of paper. Somebody has started this for me. And then what you get is somebody who's more excited to do the work, somebody who's more energized, somebody who's less burned out and they're able to think more creatively and solve problems from a greenfield first principle space as opposed to the this is the task I must execute, here's the result. And then they just go along the path. Right. So that's why I say I don't think we would resource differently, but I think we would be able to have different results from the resources that we have. And frankly I think it would give us a different reputation in the business too because then we're not sort of the company where people don't. Or the, the team sometimes where people don't have visibility or they're not sure what's happening in legal or oh, it's stuck illegal. Right. This uh, a thing that people love to say, but I think the advent of AI would is really going to change that for a lot of us.

Tonkean: You know, I think it's super, super important point because the tendency is to go and say, oh, AI is going to, you know, take away jobs. Right. And I think even people that are as part of the like closer to the, to what it actually means, AI and so on, they know that that's kind of like probably not true, but at the same time because it does take away tasks, it is confusing. So I appreciate you kind of describing the asset of work I do think you also touched on. Working with outside Console has to bring up the idea that there's some ways of working especially around the hourly rate and those type of things that I mean they got to break down now. What do you think? Do you think it's going to. This is, is this going to help change some of the structures of how we, how we work on those areas?

Jasmine: Well, from my vantage point, I think it helps us as consumers of the very technical services that outside council delivers to be better users of it. And specifically, what I mean is sometimes when I know nothing about a topic and I have to go get some research on it, I almost don't know what question to ask. Right. And so it's harder for me and I can Google, but I, you know, then I'm spending more time and maybe I'll press for time. But what I'm doing maybe in that old world is I'm going to outside counsel to say, hey, I have this question from an internal partner. What things do you think I need to ask back or focus on? Right. And then I put the scoping a little bit in their hands to help me figure out how much money I need to spend based on the universe and the complexity of the topic. And it's harder for me to time box it or substance box it in that old world vision. Right. I think what AI has really helped me do in my practice anyway is literally if I get a question from a partner internally where I don't know anything about that, I will type in my internal partner asked me this question. What questions should I ask back? To better understand, I need to prepare a memo summarizing the risks and blah blah, blah, give me a quick summary of the lay of the land so I try to get at least a baseline understanding of the issue. So then when I go to outside counsel, instead of this broad ask, I'm specifically saying this is the issue I have. I understand that these potential laws or regulations might be implicated. First, do you have the off the shelf materials you could share with me? Second, do you have, you know, a quick memo that you've done for other clients or whatever where I could get insights? Third, you know, how can I deliver back the best answer? And then finally, based on what I research I've done, I think this is an hour long project. Can you timebox it? Right. And I now have been formed. I could say, I think you could do this in an hour as opposed to before. I just maybe wouldn't have known. So I think that's how the structure is changing. I don't think I'm not bought into the camp of this is the death of the billable hour. Or you know, this is, you know, it's going to completely upend everything. Instead, I think it's going to make me a more aware and conscientious consumer. It's like someone buying a car who now has access to the financial models on the Internet. Whereas before we were just walking into the finance office and hoping that we understood their math.

Tonkean: This episode is brought to you by Tonkin. Tonkin is the operating system for business operations, providing businesses with the building blocks to orchestrate any process with no code or change management required. Contact us@tonkin.com to learn how you can build complex processes fast. Yeah, I think it's very, it's very true. I think the. I think it does beg the question of over time, you know, if you assume progress of any. In any rate, it will get to a point where the use of that outside console would actually be console, you know, so it's like, you know, I just need another person to bury the weight in many ways of the liability, you know, not only from a technical perspective, just from like, from a. From a real human to human perspective. Like, you know, I'm not an expert at this. I did the research, I used this tool, that tool. You know, I think I have a good idea of what it is. I need another eyes on it and another sort of like someone to share the. Which. Which by the way, the smaller the company is, the more actually I think there's clarity of why you use. When you use Altrain Console, oh by the way, any outside, uh, services versus in house, you want to delegate some work, but you also want to delegate some of the responsibility to essentially have that confidence that I have checked it with someone that is an expert and therefore, even though that was my hunch all along, um, I'm also kind of validating it and I don't know that's how I feel that this is. Will end up in. Is that there's more and more of the work is going to move away from the actual work and more into sort of the fact that we, as we go about different projects, different problems, different decisions, we rely on each other to kind of like not being alone in that decision and less about the assets that comes from it.

Jasmine: Yeah, I think for me, two, two things are true. One is there will always be technical expertise that outside counsel has in certain areas of the law that a. I just can't get anywhere else. Right. There is nowhere else that that expertise might exist unless I have that lived experience or unless I'm willing to do a lot of work to read and learn and buy tools that are giving me access to that information. And I think that that will not go away. Especially complicated, nuanced laws that intersect with one another and where it would be much more efficient frankly for me to just go ask outside counsel what the rule is as opposed to me spending all those hours. So I think that actually flips the model a little Bit on its head. Like, I think there are moments where it's cheaper to go to outside counsel, say, just tell me the answer to this. But it's gonna take me way longer to figure it out. On, uh, the second part, I think that sort of like, I just want somebody else to validate what I think is. Right. I think what that the value of outside counsel there is their judgment and their experience. Right. So outside counsel represent hundreds, sometimes thousands of clients who have done things a myriad of different ways. And in certain areas of the law, there is a little bit of gray. Right. And so sometimes what you, as a consumer of outside counsel's services, want to know is, what's my risk exposure if I did it this way versus that way? Or what are some creative solutions that I may not be thinking of at all? Right. So I do agree with you that it's this thought partnership, but it's less of a, uh, can you rubber stamp it? And more of a, can you partner with me on how I can creatively solve this problem? And based on how you have seen this across the market and maybe in a way that I haven't, because I'm, you know, just focused on what my company's context is. So I find sometimes that outside counsel can help me take my blinders off and be like, okay, first principles. How do we think about this and solve it from a different vantage point? And the best outside counsel, I think, will always enable you to do that in a way that is efficient and effective.

Tonkean: Yeah. And the reason I agree and the reason I. I was kind of like double clicking into it. It's actually, there's nothing to do with outside console specifically, because I think if you just take that, uh, that paragraph you just described and you switch outside console and switch, you know, you as like, uh, an in house.

Jasmine: Yeah.

Tonkean: And you just switch it with two departments, even within the same company.

Jasmine: Yeah.

Tonkean: It is a little bit of what. What's going on, which I think is very interesting when you think about how we work and kind of like, what is the not even distant future did the very like 2 to 5 years future look like when a lot of the tasks before there was a very clear walls of. I need a slide deck that looks good. I need a designer for that.

Jasmine: Yeah.

Tonkean: I need a, you know, I need a draft for a. For a blog. I need a writer for that. And then again, AI, all the different tools are at certain stages right now. I'm assuming they're all getting better. Okay. Like, at one point, you really get to a Thing that, oh, you want to research on a company, you want to click, okay, here's the profile of a company. Or you want a mock, you know, diagram of something in one click and you have a mock diagram. And so the task become less of an issue. What's become an issue is like, is that even good? Right? So like, I think the very first version of use cases of ChatGPT was, you know, create a blog, you know, create an email content, whatever. It creates it immediately. So everyone like, whoa, that's crazy, you know, because it was crazy. It was. There was nothing like this before. But isn't any good.

Jasmine: Yes.

Tonkean: You know, I mean, and so you can create amazing things with it, but you need to be good to a point too. And so you sort of like start to create, I, um, think what actually will be healthier relationship between people and department and teams and, and whatnot, which is sharing the responsibility, sharing like you said, the experience, sharing the judgment, which is another way is taste. You know, there's like, you can, there's parts of a judgment whether it's taste, but you know, things that you kind of like, like you said that you get good at, but you also that you like to do. And so which makes you even better than the execution of the task because you're passionate about it and then you're able to start sharing that and the groundwork of generating the first draft or directing the walk into the, into the right place, the time we spend on it is going to go down. Uh, and so I think the quality is going to go up. But also the, the, the fun of it.

Jasmine: Yeah, I totally agree. I. It's. You know, there's so often when you're just staring at a blank page and you just wish there was something for you to revise instead of having to write it from scratch, and that can be very intimidating. And you know what's really interesting is, um, Ironclad did a state of AI legal report last year where we asked folks, how many of you believe that AI is going to help with your burnout? And 76% of respondents said that they believe that AI would help reduce their feeling of burnout. Right. And I think it's because A, sometimes we're isolated and doing this work and we just want someone to talk to or someone to bounce an idea off. Uh, B, sometimes we do have to do the same thing over and over and over again and that's less fun. Right. And so if we can automate or find out a way that's less intensive on us to do that baseline work, we get to then do the fun stuff, right? But to the point, I think you very well made, you still have to be a good lawyer to know if the baseline was good. Because if, when your starting place is bad, it's not going to be fun, right? It's not going to be good fun work. Because you're not going to be delivering a good work product that actually helps your client succeed or do whatever it is that they need to do.

Tonkean: I don't actually think there's a way out of that, like in a good way. I'm saying this is my personal opinion. But if you actually trying to look at some of the areas where AI is the most, most adopted and kind of like most impactful is actually again, like most other technologies in the engineering space, right? You can, you know, it can really go very, very far by itself until it doesn't. You know what I mean? And so where is that, where is that sort of like line that is currently making mistakes? Okay, maybe it was like, uh, you know, couple yards a year ago and maybe now it's like 50 yards. And then maybe in the year it will be like 200 yards or a thousand yards. It doesn't matter. There's gonna point, gonna be a point, you know, where it's not gonna do the right thing. And, and, and I think if you design, if you design the kind of next generation of processes of organizations of responsibilities, I think it would be fascinating to kind of like design it in a way that leverage what exists, what gonna be better. But also understand the fact that we're just people working with other people, uh, at the end of the day and how that all kind of come together.

Jasmine: Yeah, I think that's right. And reminding ourselves that there is no judgment in the exercise of or in behind or powering generative AI. It is pattern matching. Right. And so you can ask for a red line, but you can't ask for a suggested what it like, tell me what my risk tolerance should be. That's the job of a lawyer to determine based on the facts and circumstances as I understand them, what should this company's risk tolerance be? And what does that translate into how I redline this contract? But of course you can ask, you can ask it for red lines, but that doesn't mean that those are the right red lines for the context or even the right red lines, period.

Tonkean: Is that old movies or cartoons? It's like, you know, you fly in the jet and like eject, eject, eject. And it's like the person decides like, no, I'm going to do it, you know, and kind of like shift the, the steering wheel. And yeah, they might very well hit the wall or they might escape it. But from all terms of purposes, the, the data shows that they should eject and they still might have made it. That risk, that decision, that is the difference. That's the sort of the judgment, that's this experience, that's the skill, whether that risk is worth taking and what's on the other side of it. So I think it's fascinating and I think it's crazy to me like how many layers they're potentially here. And I'm kind of almost like on a, uh, crusade to try and understand what of it is just the same. And that's just yet another iteration of technology getting better versus it's big enough of a change where some core ways of how we do things are going to change. I'm not sure yet. Vertex is clear to me yet.

Jasmine: Yeah, I think it's changing every day and I'm a both and kind of person. So I do think that it is fundamentally shifting the ways that we work. And I do not think it's going to replace us. I think it's going to augment us. Right. I think it's going to make us better and it's going to help us focus and it's going to let those of us who really understand how to leverage AI, how to use AI, how to be discerning about the output of AI, to continue to practice at the top of our games. But if instead what we're doing is relying on AI to tell us what we should be doing, that I think is problematic. And I think that it's going to lead to a very different conversation about the value of AI and frankly the value of people and how they use it.

Tonkean: Yeah, that's true. Well, I guess as you kind of like summarize back some of the twists and turns of the career, which I think again, very impressive. So, uh, kodos for that. But you know, what are maybe the good advice you had early in the career that you, you know, kind of stick with you and maybe we'll survive the, this next iteration of changes.

Jasmine: Yeah, I think early on I got advice to stay true to my authentic self, to be authentic. Right. Especially as a, a young litigator trying to shape shift and code switch a little bit in different environments, I had a hard time practicing law that way. I've. I have a hard time being a person in the world that way. And so I think when I got the advice to like, you could be who you really are and you could be a really phenomenal lawyer and you could be very successful, all of those things can be true at once. Like, embracing that and mentality, I think has been really, really essential to my career. And I encourage other folks who maybe struggle with multiplicity and identity to consider the same approach.

Tonkean: I love it. Awesome. Well, if anyone wants to continue nerd with you on any of those topics, where, where can they find you?

Jasmine: Um, you can find me on LinkedIn, Jasmine Singh. Or, uh, you can send me an email. Jasmine Singh ironcladhq.com Awesome, Jasmine.

Tonkean: That was a pleasure. Really appreciate it. It was fun.

Jasmine: Thanks so much. I really appreciate you having me on.

Speaker C: I hope you enjoyed this episode of Modern Business Operations. You can see the show notes and all of the resources mentioned on, um, Today's episode@tonkin.com mbopod thank you for listening and be sure to subscribe for updates on future episodes. And if you're interested in staying up to date on the latest in business operations technology, head over to tonkin dot com.