The Mindset Shift, AI Hallucinations, and the Return of the Legal Apprenticeship with Ceschino Brooks de Vita

Welcome to Studying Law Around the World. I'm Claudio Claus. In each episode, I talk with lawyers, law students, and professors from different parts of the world to talk about legal education, careers, and what the profession looks like in real life. We talk about the hard parts, the surprises, and the decisions that shaped their paths. Whether you're planning to study abroad, thinking about working in another legal system, or just curious about how law works around the world, this podcast is for you. Today I got the privilege to interview and am joined by Fiskino Brooks de Vida. He's the founder of The Legal Tech Guide. He's a former big law lawyer and a leading voice helping lawyers make sense of AI, legal tech, and the future of legal practice. He has a very interesting channel initiative. He's also a Harvard alum. Thank you so much for making the time to come to the show today, Chesquino. Yeah, Claudio, thanks for having me. I'm excited. Absolutely. And to start off the show, I'd love to hear a little bit more about your story. You know, you've worked big law, legal tech, marketing, entrepreneurship. There are so many interesting points to your career and to what you do. And, you know, why don't you tell us a little more about, you know, that story, that intersection? What are some of the biggest mindset shifts you had to go through when you were moving from practicing law into building businesses and products around the legal industry? Sure. Yeah. So I'll, there are a couple parts to that question. So I will say a bit about my career background and how I shifted from one sphere to another. And then, yeah, the mindset shift is a big part of that. Fairly important for anyone who is considering, do they want to make their own shift? as lawyers to something legal adjacent or something completely different. So I went to law school straight out of college, went to a big firm in New York City, and I grew up in a household that's very arts and letters. So my mother's a literature professor, grew up with lots of rooms full of bookshelves filled with books, lots of art, lots of good stories, an appreciation of storytelling and art and craft. But I didn't really have much exposure to law or to business. So there were no lawyers in the family. There was no family business. And so as I was studying and then practicing corporate law, I realized I wanted to learn more about the business side of things. Why were these deals being made? What was the value that they were providing to their investors? And so I ended up going back to school for an MBA, focusing on marketing and entrepreneurship. And I made my way into the tech world and eventually into legal tech specifically, where I came in having practiced law. I didn't need somebody to explain to me what lawyers do or how lawyers think or what lawyers are concerned about all day. I was able to just leverage my background as a lawyer and my more recent expertise in marketing and startups and put that together and help companies grow. And so that's, that's basically the shift I've made. A former practicing lawyer, still licensed, and now I work in legal tech trying to help some of these companies that are making legal software and now AI solutions, help, help them reach lawyers and explain the value of what they're building. So as you mentioned, the mindset shift. I think that's a tricky part. When I've talked to other lawyers who have, who are looking into changing careers or others who have successfully made the leap, you really do have to, your role within the organization changes. If you're going from, even if you're going from, say, a law firm to an in-house role, but if you're leaving the legal role entirely and say, in my case, I work in marketing or you're working in, could be sales, could be legal engineering, legal ops, product management, lots of different roles you have to look at. What does this organization need and what does this role specifically call for? When you're practicing law, it's primarily a risk management function, whether, and that's whether you're in a law firm or whether you're in-house. What you're doing is you're helping your clients manage their risks. And so in corporate law, you have some sort of business and maybe they're a growing business or maybe they're a mature business, but there's a certain level of risk that they can tolerate and a certain level that they can't. So there are, there are a couple of facets. Facets to that. One is, even if you're still in a legal practice, let's say you move from a big law firm where the focus is, let's, we have to turn over every stone. We have to find every potential issue. We have to identify everything that could possibly go wrong with this deal and flag it and then leave it up to the business people to decide. Whereas let's say you're in-house, well, then the conversation shifts. You're not just supposed to find every possible risk and tell people there's the risk, figure it out. They want you to come up with a judgment. Yeah. You have to help them prioritize. So how big is this risk? How likely is it that this is going to happen? And when you weigh the magnitude of the risk and the possibility that actually happens, you have to weigh that against what are the goals? So in a startup, you're trying to grow. In a profitable company, you're trying to maintain your cash cows. Basically, you have a profitable enterprise and you need to keep it going. So you need to understand the type of organization you're in, what their goals are, and how you fit into that big picture. And then, you know, moving beyond legal practice, when you're in a go-to-market function, marketing, sales, even something like customer success, which a lot of these positions in startups are focusing on, your goal isn't really risk management. It helps to have that perspective where you can, you can identify the risks and see, this is how this could go wrong, or at least how we might get tripped up. So let's keep this in mind, but your function is no longer just to say, okay, I'm here to identify all the ways this can go wrong and let somebody else decide. Your function is to help the company grow. And so the mindset you bring to the table, it's good to have that attention to detail that serves you well as a lawyer, but you have to leverage it in a different way. So yeah, it really depends. And the best way to learn is to ask people who are already in that job function and ask them just, what do you do all day? What skills do you use? What do you look for when you're hiring somebody? Because there's not just one skillset that will serve you equally well in every career path. That's amazing. Thank you so much for sharing those. I'm curious here, trying to drill in a little more into the whole you know, legal tech, AI, and how that has been, you know, played a role. I do believe it's pretty fair to say that a lot of lawyers are feeling overwhelmed by legal tech and AI. You know, each day you get a different pitch from a different vendor and many platforms that are promising to, you know, quote unquote, change everything. So as somebody, someone who also has a lot of experience with marketing, from your perspective, how can lawyers separate the real value? What, what are, you know, some things that they should look into before just, you know, following the marketing hype, so to say? Yeah, it's a great point. And that, that line you mentioned, it's going to change everything. From my perspective as a marketer, that's actually a terrible way to market this stuff because most people don't really want to change everything. Maybe they want to improve a few things here and there, the things that give them headaches. But if you like your job, if you like your career, and if you like the work you do, You don't actually want to change that. So there is this disconnect right now between what a lot of legal tech companies say and what a lot of AI providers say and what people really want. And I think that's not isolated to the legal industry, but it is very prominent in the legal industry because you see all these legal AI companies saying, hey, we, we created your new, a new lawyer for your team, or it's your new paralegal, it's your new legal clerk. And I think that's kind of silly because if you, let's say you started your own law firm. And you hire people and you pay those people, you're probably pretty proud of yourself for creating jobs for people. So the last thing you want to do is hear that this robot basically is going to replace the people you know and care about on your team. So I do think that they're even just at a fundamental level, a lot of these companies are having trouble really understanding who am I talking to? What do they do? What do they care about? And how do I reach them? And so I think that's the first thing. Look at what the company says about itself. About its products, about its customers, about the people using it. Because if all they're saying is we'll help you do X, Y, and Z faster, and we'll replace your team, that's probably all they care about. And if that's not what you want, then they're probably not the right partner for you. So definitely look at, look at it as more than just a software choice. It's not just like buying, buying a Microsoft Word license. You have to look at the people behind the product. You have to look at how they treat their customers, like even how they treat their own employees. What is their mission? What do they want to do? Are they just automating paperwork or are they really trying to provide something that provides value to lawyers in your type of practice and your type of organization? So that's, that's the main thing. And one of the best ways to do that, there are different resources out there. Certainly I created Legal Tech Guide. There's a website and I have a podcast and now CLE. So I have some of my own resources. There are some great benchmarks out there like Anna Guo with Legal Benchmarks. But one of the best ways is just to ask people, you know, who are actually using some of these tools and see. How are they using it every day? Is it providing real value? Not just does it work, because something might work, but maybe it's not worth the price you'd have to pay every month to use it. So you have to figure out for your firm, for your practice, your department, is this a tool that serves your needs and helps you do something that you need, you need to do? Not just something that has a lot of funding or they have some nice advertisements, or you heard a lot of other people are using them. That's amazing. Thank you so much for, for explaining that so nicely. I understand also that, you know, the LegalTech Guide is a vendor-neutral resource. Are there a few gaps that you see in the legal industry that maybe pushed you into building it? That, and also into making it something educational instead of simply, you know, another marketing platform? Yeah, well, that was precisely it. Having worked in legal tech marketing for years now, I was actually kind of tired of some of what we've talked about, where you have a lot of these companies that are really just missing the mark with their marketing. And I think the best way to, if you're selling something of real value, the best way to, to sell it is to tell people what is the value you're providing. I feel like some of these companies, maybe they feel like they need to trick people into it or, or else they're just hiring people who don't really understand the work and therefore they don't know what to say and they're trying to figure it out as they go. But really, if you've made something of value, just tell people what is the value? What does it do? How does it fit into their day-to-day? How does it make their life better in some way? And when you think about it, that's basically education so that. That was the goal with the Legal Tech Guide. The way I like to think of it is, you know, I was a corporate lawyer. I was on the transactional side, lots of contracts, drafting contracts, drafting memos about contracts. I'm not a litigator. So when, for example, I needed to research some topic when I was practicing law, what I did, you know, in law school, at least in the U.S., they give everybody access to Westlaw and Lexis and tell you, go knock yourself out. Just keep searching until you've found just about everything you can on the subject and you figure you're done. Of course, when you get to a law firm, they don't want you to do that because you'll bankrupt the firm. So instead they have a library and there are competent librarians in the library and you go down and say, I need to know about this subject. So they pull out a big tome called the treatise and somebody has done the work of summarizing the applicable law in that area. And all you have to do is read the summary and check for updates on those cases and boom, you're done. And so I thought, you know, why isn't there something like that for legal tech? And so basically I created it. The idea behind the guide is there are lots of different categories of legal tech. There are, there is some overlap, but I really wanted a resource that would help people understand from a buyer's perspective, when you're buying solutions and when you're looking at all these different tech solutions, how do they really relate to each other? How do people actually buy them? How do people actually use them? And so that's how I sorted it. You know, document automation, for example, there are some tools that help you automate lots of different types of documents. Some are just for litigation specifically. So instead of just trying to collapse everything into one category, I've even seen, you know, some analysts will call contract lifecycle management part of document automation. And it's like, well, there's really more to contract management than just the document part. There's also tracking deadlines, tracking obligations, managing your contract data, your counterparties. I think some people try to make things fit. too neatly for their own purposes. They're just trying to minimize the number of categories. Or alternatively, you have a lot of vendors who just talk about their own category. And of course they're not selling something else, so they don't talk about something else. So that was the idea. I want to give a thorough resource that covers the entire breadth of the legal tech vertical, but not necessarily from a vendor perspective. It's from a buyer perspective. How do people actually buy and use this stuff? The AI revolution is quite different from the other industrial revolutions, so to say. where before knowing this or that was somewhat of an advantage, but this time around for the AI revolution, expertise and experience make a big difference. You know, how do you think young lawyers should balance, you know, learning the legal traditional skills with learning how to use AI tools? Yeah, it's a great question. So first, I absolutely believe that AI is best used in the hands of people who know what they're doing already in any given field. So it could be law, it could be coding, could be marketing. Whatever, which is great if you have experience. But yeah, if you're trying to get that experience, that then creates the question, how do you, how do you get it when so many people are automating the things, like you said, that used to go to junior lawyers? So a little more color on why you need experience. One big issue is simply hallucinations. So AI will confidently tell you things that are not necessarily true. And we've all seen plenty of examples of lawyers getting censured or even Recently, I saw a district attorney got her license suspended because she was, she had like several AI hallucinations in a brief she submitted to a court. You might think that by now it's been a few years, people would be a little more cautious, but this keeps happening. So clearly, uh, there's another example with Sullivan and Cromwell. They submitted something to a court, I believe, and it was full of errors, hallucinations from AI. So clearly at all levels of law, this is happening right now. So a couple of things. One is, There, in order to catch that sort of thing, when apparently everybody throughout the profession is susceptible to it, you really need to know what you're doing. You need to know what right looks like and what wrong looks like, or else you can't discern between the two. And so if you don't know what is wrong, then that could be you next time. So that's the main thing. You need to understand what does good look like and how do you make, how do you differentiate between something that is still a work in progress and something that is actually good? So that's the first thing. And that comes with experience. So the second part is how do you get that experience when again, you have all this talk of, well, entry-level jobs are all going away and a lot of employers are saying, well, why would I hire somebody now when I can just automate this part myself, check the work and, and, and yeah, finish it without hiring any more junior employees. And I think there are at least 2 camps here. So you really, if you are a young job seeker, you need to find somebody who does, who rejects that mindset, who says, no, I'm building a business. I'm building an organization that I want to last more than 5 5 years, more than 10 years. I'm building something that I want to be around and even to survive me. Because those people are still hiring people and still training people. It's effectively an internship, right? But in certain countries you have this kind of apprenticeship requirement and then, so you spend some time being basically a law clerk before you are admitted to the bar. So in the US we don't have that. Maybe we should. But yeah, I do think in general, this is where the legal profession is going to kind of return to. So for a long time, especially in the US, if you're going to big law, you have these highly leveraged firms, Lots of associates, very high ratio, like 10 to 1 ratio of associates to partners of some firms. And you're just not really getting good mentoring, not really getting good training. So I think because it no longer takes such a big team of people, but you still do need younger lawyers coming up who understand your business, understand your practice, and can help you take on clients, get new clients and so forth. What we're going to see is probably more of a return to the old apprenticeship model where you have a partner who has the book of business. They understand the practice of law. They understand how to bring in clients. They bring in a moderate number of associates, maybe just, maybe it's even a 1-to-1 ratio, uh, 'cause they just don't need that many warm bodies. And for a couple years, as the lawyer, you are just learning how to do this stuff. You do a lot of work, not because the firm needs you to do it yet, or the practice group needs you to do it yet, but you, but because they want you to learn so that a few years down the line, you'll be ready to run deals or run cases. So I think that's where it's going. And so if you are just looking for your first job or, or you're even your second job out of law school, find those people who believe what I just said, that no, they want to build for the future. They want to bring somebody on and train them. And even if your work isn't perfect yet, like they, yeah, they could do it with AI now, but they want competent people on their team. So find, find people who are people first. We still exist. Fantastic. Well, I really appreciate you bringing that perspective. And another thing that I wanted to ask you is, is you've seen technology from both sides, right? So you've seen it. as a practitioner in legal tech, how it works inside a law firm, and then also how it works from the company side, right? And then also as a customer in many ways. So what do legal tech companies maybe misunderstand in your point of view about lawyers, about how lawyers actually work day to day? Yeah, absolutely. And it really depends on the company. Because as you said, there are those who have at least one lawyer as a founder, or they have, they're bringing in lawyers in sales, for example. So it really depends on, are there people who understand the practice of law who are embedded in product decisions and company decisions? So how this company, what features it's developing, why it's developing them, and how it delivers them to the buyers and end users, you know, the lawyers who are actually going to use this product or not. I think there are many people outside the practice of law who believe that practicing law is all about producing documents. So if you're a litigator, you produce briefs and memos. If you're a transactional attorney, you produce contracts and that's it. Because for these non-lawyers, that's all they see. They see the written work product and they assume, oh, this is the practice of law. But really, again, and this is not just in law, it's in any given field. If you're a software engineer, for example, yes, you produce code, but there's a lot of thought that goes into it. And I think people have found that out with vibecoding that yes, you can, you can create a prototype or you can create your own fun little game or something like that. But if you really want to sell something to other people, especially if it's business-grade software, you need somebody who actually understands how to build software. And there are security considerations, there are data privacy considerations, and even just stability, making sure the thing is up and running 24/7. So law is pretty similar. I think it, because it takes longer to see results from law, court cases take forever, contracts, it's really only if it gets disputed at some point that people really scrutinize what's in the contract. So I think it's taking people longer to realize it, but as we see with all these pro se litigants who are getting their cases dismissed from court, sure, the fact that AI produces a decent looking memo at a glance doesn't mean that it's substantively good work. When you see a lot of these investors and engineers and other people with no legal experience who are not bringing in that legal expertise, a lot of them are getting tripped up by that where they're saying, oh, well, lawyers produce this paperwork. figured out how to automate this paperwork well enough to, it looks good enough to me. Therefore we can replace the lawyers now. And of course, if you're trying to sell that to a lawyer, the lawyer is going to look at it and say, well, this doesn't actually work and they're not going to buy it. So yeah, there's still a disconnect there. I have met plenty of founders at this point who are lawyers or they're working with lawyers and they're trying to build a better wave of legal tech companies and products. But there, there is still a disconnect there. So that's something I certainly recommend if you're looking for a products to buy, products to use. Look at who made it. Look at how they talk about it, like I said before, and get your hands on it and talk to other people, other lawyers who have used it and see, does it actually help or is it just another ChatGPT wrapper, for example? Going back to, to, you know, your story and your career, I see that, that your career combines a lot of very interesting things, right? We talked about the law aspect, the marketing, but also, you know, storytelling, design thinking. technology, sometimes lawyers do feel boxed into a traditional career path. If they want to have any kind of predictability, any kind of stable income, they'd have to go, you know, into the traditional path. And what would you say about, you know, building a career that mixes multiple interests instead of, you know, understanding that a successful career is to follow in a single lane, become specialized in one area of law and And kind of stay within that domain? Yeah, it's a good question. Again, I think there are a couple of parts to it. One is I think it's increasingly going to be necessary to have a multifaceted career path. Because the more, when we're looking at AI and automation, the more repetitive a person's job is, the more susceptible it is to automation. So if you come into your job and you're every day you're doing the same thing, sitting at your desk, doing the same thing you did yesterday. Going through the same thing. Let's say it's small contracts and you're reviewing 10 of them a day, but they're not very complex. That's highly susceptible to automation. Anything you do that you're, it's basically you're plugging information into a template, for example, or again, there's, there's a highly stable process that can be repeated steps 1 through 5 and do it again on the next one. That is the work that is in more danger. But as plenty of other people have observed, Whenever society automates certain things in general, more work is created. If you, so contracts, for example, used to be on paper and then typewriters were invented and then computers were invented and the internet. And it was easy, well, in theory, easier and faster to produce contracts. But that didn't eliminate lawyers. Instead, you just have bigger and bigger contracts, bigger and bigger deals. And the more, the more complex the technology, basically the more complex the The deals that you can create. And so I think that's what we're going to see in general. Spreadsheets are another example people like to raise that when those came out, a lot of people said, oh, what do we need accountants for? But no, as it turns out, you still need accountants. And in fact, accounting has gotten even more complicated. So the more sophisticated the tools, the more complex the work can become. And I think that's what we're going to see. Who knows exactly what that looks like with AI, whether that's AI in law, AI in coding, AI in other fields. But the more sophisticated the tools, the more you can do. So I think this is, and this is what people are really exploring. Once you automate most of the stuff you're doing today, what does that open up for you to do that you couldn't do before? One example I'll raise is when I was in a firm, we talked about assembling all of our contracts and looking at the different versions of all these different clauses that had popped up in different agreements with different clients and different scenarios and different deals and figure out the best versions of those agreements and the fallbacks and all that. And of course there just wasn't really time to do this. We did eventually get at least one enterprising first year on it, and there's a big lift to just document some of the clauses, but it was a huge lift because everything had to be done manually, you know, redlining individual clauses against each other one by one. It was a pain, right? So normally when you have these kinds of projects, they don't get done because everyone's billing hours. And when you're done billing hours, you don't want to stay in the office just to do extra work that's not billable. But now with AI, you can actually think about that. You can say, okay, help me surface all 5 versions of this clause, or I mean, not, not just 5 versions, right? But however many times this clause pops up across these different agreements, help me surface however many different versions there are and compare them and redline them and figure out, okay, what should be the default version? What should be the fallbacks? Right? So that's, I think, the real transformative potential that once you have these tools, you can start doing things that maybe you talked about doing, maybe you thought about doing, but you just weren't really able to do before. Now, again, you have to check for hallucinations and you You have to know what your goal is and all that. You have to know what good looks like. But yeah, that's the really exciting part. How does this transform our work and enable us to go beyond the repetitive stuff that nobody really likes doing the repetitive stuff anyway? If you're coming into the office and doing the same thing all day, every day for 40 hours a week, 60 hours a week, 80 hours a week, depending on your type of practice, that's probably not feeling fulfilling to you. So I think there's a lot of potential. to transform the way we work, but you have to be active in shaping that, figuring out, okay, I've eliminated this many hours of rote week per work, rote repetitive stuff. Now I'm going to experiment and try to do something new. It's been very, very nice to hear a little bit more about your thoughts on careers and how knowing how to deal with AI might be, you know, something that we have as a big advantage as well. But I really appreciate you mentioning that, that maybe not being a super specialist might be helpful in many ways. This part of, you You host a podcast yourself, The Future of Law Is Today. Tell us a little more about, you know, how the idea came about and what are some of the conversations you're having? After speaking with so many people who are in a way, you know, shaping the future of the legal profession, you're having so many interesting guests. What are some of the themes or concerns that you're listening to repeatedly? Yeah. So a little bit about the podcast. So late last year, when I announced the launch of the LegalTechGuy.com, I was pleased to see that a bunch of people got in touch and said, this is great. This industry needs this. How can we get involved? How can we help out? And so based on some of the conversations I was having, I thought, well, I'm hearing some great insights from these people. 'Cause I was talking with people who practice law, people who work in legal ops, people who are building their own legal AI. And one thing I've been telling legal tech founders for a while now is start a podcast. It's a great way to get your name out there and build trust with people because they'll see this is how you think. This is your philosophy on law and what legal tech should be and how you're helping lawyers. Just do it. Even if you don't see the immediate lead gen return, just do it. And so I thought, well, you know, maybe I should, I should take a taste of my own medicine, so to speak. And I have this opportunity, I've built this platform, so I'll just launch my own podcast. And so I went ahead and did that. And I've been running that since November. And like you said, I've been able to talk with a bunch of great people from around the world who are all tackling not just legal AI, although that is a big part of it, but legal AI automation, the practice of law, legal operations. Some of them are external consultants. So just, they're all looking at how are we shaping basically the practice of law? And so that is really the main takeaway that I think in law especially, it's easy for people to think, to get kind of stuck in this mindset that this is the way things are. So you get your degree and you learn the rules and then you learn both the rules of your area of law and the rules of how a legal career works. And you follow the rules and you'll be paid well enough, right? And that's just how things are. The profession attracts people who think in terms of these are rules and you have to interpret the rules and understand the rules. But I do think there's this tendency to be kind of passive and say, okay, this is just how things work. You accept it and that's it. And so when you're looking at AI, for example, and like you were saying, all these companies and pundits are saying, oh, it's going to change everything. That can feel unfair. I like how things are now. I don't want it to change. I don't want to learn new things, but. Really, I think we all need to be proactive about how we work and how we manage our careers, how we manage our organizations, our teams. And so for better and for worse, all this AI hype right now and the kind of the chaos around it is forcing everyone, or at least giving everyone an opportunity to rethink, well, how do I want to practice law? And what do I want my career to be? And what do I want my firm to look like? Or how do I want my legal department to function? So that's the main thing that's come up for me is that the people I've talked to, uh, Of course, plenty of them are founders. So this is part of why they have this mindset, but they, they share this mindset that you have to be proactive and intentional about what you're doing and what you're building. So don't, don't think that a legal career just happens to you or whatever sort of career. Your career doesn't just happen to you. Your organization doesn't just happen to you. Work, you know, life in general does not just happen to you. It's what you make of it. So be intentional, be proactive, and really shape what you are doing with your work. Thank you so much for making the time to, to come in the show today, share some of your insights. It's been great to learn from you. And I want to invite the listeners here as well to, to go and to learn from, from your show, you know, make sure to check out the show notes down below and we'll make sure to give him a follow. Thank you so much for coming on the show today. I appreciate it. Thanks for having me. Thank you all for tuning into today's episode and we'll see you on the next one.