Fresh Voices on Legal Tech with Anastasia Boyko

Episode Notes

Transcript

Announcer:

Web 2.0. Innovation, trend, collaboration. Got the world turning as fast as it can? Hear how technology can help, legally speaking, with two of the top legal technology experts, authors and lawyers, Dennis Kennedy and Tom Mighell. Welcome to the Kennedy Mighell Report here on the Legal Talk Network.

Dennis Kennedy:

And welcome to episode 417 of the Kennedy Mighell Report. I’m Dennis Kennedy in Ann Arbor.

Tom Mighell:

And I’m Tom Mighell in Dallas.

Dennis Kennedy:

In our last episode, Tom and I debated the value of the classic 60 tips and 60 minutes CLE format and whether it’s a time for a rapid fire evolution of that concept. It’s a fun and informative episode. In this episode, we have another very special guest in our Fresh Voices on Legal Tech series. In Fresh Voices, we want to showcase different and compelling perspectives on legal tech and much more. Tom, what’s all on our agenda for this episode?

Tom Mighell:

Well, Dennis, in this edition of the Kennedy Mighell Report, we are thrilled to continue our fresh voices on Legal Tech interview series with Anastasia Boyko, legal innovation consultant. We want our Fresh Voices series to not only introduce you to terrific leaders in the legal tech space, but also provide you with their perspective on the things you ought to be paying attention to right now. And as usual, we’ll finish up with our parting shots, that one tip, website, or observation that you can start to use the second that this podcast is over. But first up, we are so pleased to welcome Anastasia Boyko to our Fresh Voices series. Anastasia, welcome to the Kennedy Mighell Report.

Anastasia Boyko:

Thanks for having me.

Tom Mighell:

Before we get started, can you tell our audience a little bit about yourself? Tell us about your consultancy, what you do there, what our audience should know about you.

Anastasia Boyko:

Sure. I’m a bit of a legal unicorn in the sense that I have tried some of everything. So after law school, I spent time in big law. I was a tax lawyer at a big firm in New York and then I pivoted into legal tech in 2010. And it was like an awakening to be able to have such breadth and creativity and to work with hundreds of law firms and get a real perspective on how lawyers operate day to day across different sizes of firms, across different geographies, how they learn, how they develop, how they run their firms. And I think that’s when my operations innovation bug really got lit. And then I went over to the business side of a law firm, leading business development and strategic growth and then back to an ALSP and in legal education and in AI as well in a legal tech company.

So I’ve tried to look at the entire ecosystem from a 360 degree perspective and also having sat in a variety of different seats, it’s helped me connect the dots. So right now in my consultancy, I’m trying to help various leaders throughout the ecosystem navigate uncertainty because we don’t know what AI has in store. We’re seeing some of the changes, but we’re not sure how it’s all going to come together. And I think having a thought partner who’s seen things from a lot of different perspectives is incredible leverage as a tool.

Dennis Kennedy:

Great. Anastasia, first of all, it’s awesome for us to have you as a guest on a podcast. I enjoy attending some of the Zoom things that you do and that’s been a lot of fun. So I have always contended that it’s not easy to talk with lawyers about tech or innovation or business or all the things that they need to be thinking about even now when they really need to be thinking about innovation and I think leadership and probably succession development as well. And sometimes I get frustrated with how difficult it still is to explain these things and the benefits of technology innovation to those in the legal profession. Now, I really liked the way you were able to talk about these topics. Would you talk about your own approach to communicating with lawyers and others in the legal profession about technology innovation and what you found works well for you just in communicating with people?

Anastasia Boyko:

Yeah. So I find that communicating with lawyers is a bit of a crystal ball. So I remember being an associate and going into my partner’s office and getting guidance on an assignment in the form of three words, three words, one of which was a number. And I had no idea exactly what the heck he was asking me to do and I know he wasn’t going to explain it. So now I had to go on a wild goose chase to decipher what the actual assignment was. I think I took that posture as I started working with lawyers in the beginning of my career. I was like, ” It’s my job to guess what’s going on and to get the precise answer that’s going to make them understand the problem. “And I completely pivoted once I realized I don’t have to make it that complicated. I don’t need to read minds.

I can actually just ask what’s going on in their practice. And I think simple questions around why are you stressed? Do you have more work than you anticipated? Where are those bottlenecks? We’ll get you to the actual underlying operational issues sometimes and communication issues. I’ll oftentimes have people reach out to me and ask me to give them a list of AI tools that are going to help their practice. Well, I don’t know what’s going on for you day to day. So I push them to take a step back and tell me about where is there a time suck, right? What is it that takes you away from the strategy that you want to be in? What are you working on late at night? What are you getting pulled in outside of your control? And start going through that and asking yourself, is there a way that I can get ahead of this?

Is it a regular town hall kind of meeting if you’re an in- house lawyer? Is it having a management meeting with your team and the leadership on your team? There are so many solutions around this that may not be tech solutions, may include some tech solution and automation, but you need to take a step back and ask yourself, what exactly are the problems on my desk? And are they a function of habit? Are they a function of operations, workflow? Is it a function of people? Where does tech come in to solve that problem? I think we’re so want to come in and answer the tech question and guess what that person’s actual problem is before actually taking a step back and figuring out, what the heck is the mess that you’re dealing with day to day and then let’s parse out what tools might help.

Tom Mighell:

Jobs to be done. Yes. We talk about that a lot, but that leads a little bit into the next question, which is about competence around technology. Let’s say that we’ve proposed a tool or we’ve talked about it. Dennis and I talk about the idea of competence and the state of technology competence among lawyers. What are you seeing right now with the lawyers? And maybe if it’s more interesting to talk about it in terms of what does a technology competent lawyer need to know in terms of either legal innovation or generative AI? I think generative AI is the first thing in a number of years that lawyers have been actively interested in trying to learn more about whether they’re successful at it or not is a good question. But what does a technology competent lawyer need to know these days in those areas? And you can pick one or both to be successful

Anastasia Boyko:

Yeah, that is such a big question and I think it varies by what kind of law that you practice. And so my advice to lawyers is always just sort of understand the field, understand what tools are out there, read a handful of the blogs that are out there that are giving you high level as far as what tools exist. Are they tools for practice management? Are they tools for collections? Are they tools for intake? Are they tools for research and categorically have a sense of what those are and how they fall into the legal practice. Maybe they’re for you, right? Maybe you have a specific need when you want to test out that tool, but more than anything because I think tools are moving so quickly and oftentimes when we are in search of a solution without a problem that we don’t take the time to just understand the landscape and the context in which these tools exist because there are plenty of tools that just don’t fit someone’s practice.

I’ve had the luxury over the last 20 years of being a volunteer for bar associations and what it taught me at the beginning of my career is there are so many different ways to practice law and the majority of lawyers are sMighell and solo firm lawyers. And so understanding that large landscape and knowing that there’s no way that I can tell any individual lawyer what specifically to know, I think the thing that you have to have is a big high level understanding of what exists, including some of the ethics and governance issues that come up with these tools. So you’re just generally well versed and that’s really hard because I think as lawyers, our tendencies to want to become expert on everything and it’s not possible. It’s like boiling the ocean to try to understand all of this legal tech. You have over a thousand AI companies in legal right now that is insane to keep track of.

And so I guide people to a variety of blogs, whether it’s Leslie’s artificial lawyer, whether it’s podcasts like yours, listen and understand what’s happening in the ecosystem so that you can sort of pick up the connections that are happening. You are not a technologist unless that’s your expertise and you don’t need to overwhelm yourself.

Tom Mighell:

Real quick follow up on that, which is with AI, I think AI is a little bit different from other technologies right now because, and I guess maybe I’ll ask if you agree with this, that you don’t just want to say, know what tools are out there. There are specific skills that will benefit lawyers to have when starting to use these tools. I’ve seen lawyers go to an AI tool and use it like Google and a search engine and then they don’t get what they want and they don’t understand it. Are there other skills that they need to be good at to understand how to use the tools right? It’s not necessarily just about what tools to use, but is there also a benefit to prompt engineering or other skills that might help them not get frustrated with a tool because they don’t know how to use it right?

Anastasia Boyko:

Yeah. I mean, Dennis, what do you think?

Dennis Kennedy:

So a couple of things came to mind when you were talking and also when Tom was talking, there’s sort of this current trend among lawyers of vibe coding with AI and people will go like, “I vibe coded this. ” And I’m like, “Why don’t you just use this basic … Why don’t you use like a basic document or automation tool that’s been around forever?” Like you’re trying to figure out how to do forms and things like that. But I think there is that notion of saying, it’s again, that sort of big picture to the problem in front of you is Tom and I and many others, but we have this sort of whole catalog of what’s out there. So when somebody says, “Would I do this? ” I’ve got like, “Why don’t you use this? ” There’s like all these different ways of doing things and what actually fits your problem.

So I think you can start to say, “If I have a sense of that, the big picture,” and then the skills I think evolve from that and you can start to say, “Well, in AI, there are things like I need to iterate. I need to do things like that and I can’t.” And the simpler that you make that, the more likely it is that people will figure out what skills that they need. So I don’t know, Anastasia, if that’s what you feel as well, but that’s sort of my take on it these days.

Anastasia Boyko:

Yeah. I mean, I’d connect it to the last answer I gave, which is like once you get a sense of what your problems are, maybe you choose one of the most painful problems you have and see what technology solutions are out there and see who’s writing and talking about it and see what tools exist and begin to get knowledge and expertise around it, right? You don’t have to know something about things that are maybe more tangential to your practice in the same amount of depth, but I encourage lawyers to continue to be curious. I think curiosity is one of the things that we begin to lose from law school onwards as we become more subject matter experts who are focusing. And so I feel like this is a great opportunity to play even if it’s just for a half an hour a week, right? You don’t have to dedicate 40 hours a week to understanding all of this technology, but you should start to get curious and play around with it and see what exists.

I think more than ever we have so many resources across podcasts and blogs who summarize perspectives on this and allow you additional resources and to hear more use cases. So take advantage of that and take it on as an opportunity to learn about an acute problem that you’re dealing with at your workplace.

Dennis Kennedy:

Well, one of the things I’ve always felt and I sort of feel it more keenly these days is that the superpower of great lawyers is their lifetime learners and they’re always trying to learn new things. So for me, it’s always a question of, okay, so what is it that I want to learn? In fact, my students in my class were saying Professor Kennedy as they humorously called me, “What should we look to learn right away?” And so I guess that’s my question for you is as you look out there from your broad perspective in the areas that you look at, what are the areas in the legal profession that need the most attention and how can we get people to pay the attention to say, “No, this is really something I need to learn about it.

Anastasia Boyko:

” Oh man, so many. But I would say training and development of lawyers. I think this is something that we talk about, but it’s sort of an afterthought that we don’t dedicate as many resources to. It’s becoming a hot topic because I think we’re realizing that law students aren’t ready. We’re realizing that there might be some displacement with junior talent as automation takes shape and folks are now wondering how do we train the next generation of lawyers? But it’s something that should have always been at the core of who we are as a profession. We sell expertise, right? So if we sell expertise and guidance, we should be really invested in how we cultivate and pass on that expertise and guidance. And so although right now it seems like a strange question of like, how do we get lawyers ready for AI even though the leverage model is going to be shifting and changing and is everyone going to get left behind who’s not a mid-level who has enough operating skills to now start upskilling?

I think it’s just the bigger question of legal education and legal training, which is connected to like leadership development and more management discipline. And I think those have all been sort of squishy terms that law firm leadership hasn’t always paid attention to. Some firms try and then you just get busy with client work. But it is the foundation upon which we build all of this and we began to see this with AI as the mainstream tools came out, the firms that had more operational excellence and had more data integrity, who had systems and processes and were disciplined around how they operated their firms are seeing more success because the foundation was there. And so I always go back to the people management skills, the subject matter development skills and being really thoughtful and strategic about what that looks like for your firm as you’re trying to set yourself up for long-term sustainability.

Tom Mighell:

Well, you have mentioned in the past, you’ve talked about the idea of the AI competence penalty, which I think you describe as the idea that uneven AI adoption creates structural inequalities or inside firms, particularly along gender lines. What do you think is driving this gap? Is it some of the lack of foundation, lack of training you talk about, or is it something different and is this a problem that’s going to sort itself out as AI becomes more normalized or is this the kind of thing that can harden into something permanent if we don’t do something about it?

Anastasia Boyko:

Yeah. I mean, another hot topic. I mean, my personal opinion is I think the women I know in legal tech who are pausing myself included over the last few years, we’re seeing how the tech is being utilized and how decisions are being made by the people who are creating the technology and the architecture. And I think we’re pausing because we don’t necessarily like the direction that it’s going. And I think we’re thinking about the way to utilize the tools for optimal success in the future versus let’s dive in and use them how we’re being told to use them. I mean, personally, I think a lot of the use cases people share with me are just basic operating systems that my brain runs as far as organization. And I really don’t feel like exporting it out to AI to then give back to me to then verify.

My brain does a pretty good job of communicating and architecting and keeping things on track. I don’t want it to send emails for me. I don’t want it to organize my calendar. I like being able to have an understanding of all of those things and how they’re connected. And so the sense I get from a lot of the women in AI that I talk to, I think the caution is based on what we’re seeing with regard to where it’s going. I mean, Dennis, I’m so grateful for the work that you share about how fallible some of the tools have been and I think that creates natural caution about how much time and energy you want to spend and how much you want to spend verifying everything if you have to do it from scratch all over again.

Tom Mighell:

All right. We’ve got a lot more questions for Anastasia Boyko, but first we need to take a quick break for a message from our sponsors

Dennis Kennedy:

And we are back with Legal Innovation Consultant Anastasia Boyko. We founded The Fresh Voices series that we love to hear about our guests career paths and our audience does as well. You have like a great career story that you’ve sketched out a little bit of that you have described as goldilocksing your way through the legal ecosystem. Would you talk about your own career path and what kinds of things you’ve done to get you into your current role and focus?

Anastasia Boyko:

Yeah, I mean, absolutely. So I like to tell this story in terms of what made me choose the jobs I took and what made me move and do something else. And so in law school it became very clear that I wasn’t going to practice for the rest of my life, even though I’d gone to law school with this idea of being a big time litigator and politician and judge. And then once I started doing the work of that practice, it wasn’t compelling to me. It wasn’t my calling. And so when I was trying to choose a practice area, I was choosing where I would find joy and connection knowing what I like doing. So I initially actually started in wills and trust because I like working with people and I like being with people during inflection points, but I found myself more drawn to financial services and I like operations and sort of how everything connects.

And so tax was a natural shift and so I moved to a different firm doing that work. But when I was in that work, I found that I was really obsessed about how the firm operates, like why are we redoing the same memo over and over again? Why does our business development strategy work this way? Why are we training people in a specific way? So I was much more interested in how the firm ran and the business initiatives of the firm. And so I think it was really natural for me to find a home inside legal tech. I actually wrote out all of the things I like doing and I don’t like doing. I did a lot of self-reflection for the first time after four years of practice. And I found my dream job, literally what I had written out for myself when I saw a new role at practical law, which was a liaison to law firms as they were building out their training programs.

And what was neat there is I got to come in and as I saw gaps in our own operations, I was allowed to step into those. So for the first time my career I can see, “Hey, we could probably be doing sales enablement better. Great, fix it. ” I love being able to do that. I got a lot of opportunities to go speak on panels and found a real joy in thought leadership and connecting with groups of people and sharing ideas. I led our marketing function for law firms and so it was neat to be able to shift around and I realized I liked trying things on and I liked connecting it back to the business purpose of the organization. And so once we were acquired by Thomson Reuters, I wanted to see if I could apply that inside of a law firm. So I went to the business side of a firm and I learned a lot around change management, a lot around what we communicate that we think we want to do and what’s actually possible in the day-to-day in change management inside of an organization that is both a professional services firm, but also has a lot of invested interests across the partnership where everybody has a way to derail things if they don’t like them.

So hard to do change management in that setting, right A very different approach if you’re trying to create and upskill and evolve the delivery of legal services. And so I think a lot of people figure that out when they leave practice and they go into the business operations of a firm. And so at that point I was really eager to get back into innovation. And so I went to Axiom, which is an alternative legal services provider. I led recruiting and talent management there. I had almost 500 lawyers for whom I was responsible as they were working in house on a secondment basis, but they were our employees, right? We were responsible for their careers and helping them navigate what they want also within the limitations of what’s available when, and then helping our clients anticipate when they need a particular kind of talent set. And so that tricky art of matching need and talent and then running a business in an alternative way was fascinating.

But I also learned a lot about how lawyers think about their careers, how they think about compensation versus flexibility, how they think about being in- house, being a firm, being an alternative model that gives them some more freedom. And so I love that and I love getting to build a team, but I also ran out of runway as far as what else I could achieve. And so I took a sabbatical. I started a consultancy around wellbeing and coaching at that time and then went back into the corporate world because I missed being in a team. And then I got called by my dean at Yale who wanted to build a massive leadership program and I said, “I’m happy to help.” And she asked me to come move and build and fundraise and do the entire architecture. And so that was really great because I could take what I saw from the practice and the operations and the business of law and then try to bring it back to law school to see if we can get ahead of some of the things that don’t work in the legal ecosystem.

And so that was like a full circle experience. And then I moved back home to be closer to my family and sort of went to the University of Utah Law School here, became their first chief innovation officer, thinking about how technology connects to access to justice and what lawyers do and what’s possible now with AI. And then I went back into a legal tech firm to see what’s happening in the advancements of AI. So I’ve always been hungry to learn to that point of like lifelong learning to see where there is opportunity for evolution in our profession. I am motivated by reducing the suffering within the profession because I think so many lawyers are so talented and oftentimes they’re not in the right platform and they don’t have the right tools to be as effective as they could be. And I think a lot of my obsession with innovation and disruption within the ecosystem has been to try to realign lawyers with their purpose and their highest contribution.

Tom Mighell:

So let’s talk about that innovation piece, but pivot back into AI and more particularly generative AI because practice management and innovation was one of the, among the first legal technologies to use artificial intelligence and machine learning, how do you see GenAI and maybe we can get into agentic AI affecting legal innovation? What’s the role that you see right now today in the innovation space?

Anastasia Boyko:

I mean, I think right now we’re still, I feel like we’re still sort of iterating. I know some folks feel like they’ve made headway and I think there are some examples there, but because the container for legal services delivery has been so broken and the current advanced tools that are trying to remedy that, they still operate on our guidance and I don’t think our guidance is that great yet. And I think we see this as tools get developed is there might be an idea as a tool comes to bear about what the structure should look like and then clients start influencing it and then it becomes less that, right? More features, more flexibility and it loses the container of trying to give a default best practices approach to a particular kind of legal practice. And so I watch it and I’m sort of frustrated because I feel like we make headway and then we take two steps back, right?

The more legal humans we put in the loop, the more complicated and backwards we sometimes go, right? I would love for someone to just give me an out of the box, this is how a law firm should operate, right? Take it or leave it, use this and work from it, which is what I like about some of the native AI firms that are out there. Let’s start from scratch if we had these tools and make it that. And so again, it still feels like an experimental field and folks oftentimes ask me, “What do you think is going to happen? Is it the end of lawyers?” It’s like never going to be the end of lawyers. I think who we are and how we work is going to change. We’re seeing that with the adoption rates. I think a lot of people are naturally scared as they should be because a lot of change is coming, but there’s a huge opportunity to figure out how to enjoy the practice of law again and to create better client service.

You need to stay focused during that, right? I just had done a pieceforlaw.com recently about the future of lawyering and the importance of setting goals and being deliberate and getting clear about your mission and your purpose of your firm or your organization. It seems high level, it seems abstract, but it’s literally your North Star. This is how you make decisions in uncertainty. You get very clear about what you’re about, what your colleagues are about and where you’re going and the principles that you have. Everything else will start to work itself out, but a lot of what I’m seeing, especially around technology is that lack of North Star. So people just keep getting distracted. They have tech stacks that don’t connect. They want to export all of these workflows and it doesn’t work that way.That is the wrong way to approach sustainable change management.

Dennis Kennedy:

With my class at University of Michigan this year, I started out and I asked them how many were afraid of AI taking their jobs in the future in the near future and it was everyone basically. And at the end of the class, I felt, and I told them this and they all agreed that they had a better understanding of what AI could and couldn’t do and they thought they understood like what its role could be, what the questions … They were really good on what questions needed to be asked and how to think it through, the different perspectives you have to take, jobs to be done, all those sorts of things. I attribute that to how smart they are more so than me as the teacher. But one of the things we talked about was lawyers need to think in terms of systems and that we’re so often looking to apply point solutions to systems problems and the better you can understand the ecosystem, the better off you are.

So one of the things I like about your story, probably more than you do when people hear about this, is that you actually grew up in what we like to call the former Soviet Union. And so you’ve had experience living in what some might call failed or failing systems. And how does that impact your thinking about AI and law these days? And more in the sense of what do you see as working as we look at systems that in the legal system, education system to me are two dysfunctional systems that are not shining examples of how we would create things from scratch, but what do you see that’s working and what isn’t working these days and what are the outcomes you’re seeing that aren’t just talk around that? And so maybe you can go back to your Yale experience or other things like that where you see things where people were actually taking big swings

Anastasia Boyko:

Yeah, I mean absolutely. I think watching a system like the Soviet Union die and growing up my first eight years were spent there. I think I learned that just because the system says something is a certain way doesn’t mean it is, right? There was a lot of talk about what the system operated like and then there was the actual experience of citizens in it and it wasn’t aligned. And then coming into a brand new country, I had to learn how do the systems here work, right? What is true? What is not? How do people interact in community? How do they find education? How do they find status? How do they find class? It’s a complete restart and a reorientation, not just in language but in culture, in democracy, in a new government system. And so I think I’ve always tried I had to take that outsider view because that’s my default view.

I mean, when I came as a student to Yale, I was a refugee. My mom and I came here with nothing but two suitcases. I had gone to under-resourced public schools. I had gone to a state undergrad and it was very weird walking into Yale Law and seeing folks who had a completely different entrance point to that place and were able to navigate it in a completely different way. I think for me, as I’ve gone into these systems, whether it’s the practice of law, whether it’s legal technology, especially going back to my law school and building a program, is I try to take a step back and look at the entire thing. I had a lot of notions about what law school was missing and some ideas to validate, but the first thing I did was embed myself in the day-to-day of student life. How had things changed in the years that I had been gone?

Are the same gaps there? Who fills those gaps? How do we create structures that actually deliver on what students need and not just respond to complaints or just symptoms of a bigger root problem? And so that’s how I’ve always taken on these big innovative systemic changes. So when I talk to clients, I don’t have an exact framework of how you need to change what you’re doing because every organization is different. You have a different set of leaders, you have a different history, a different set of habits and behaviors and workflows. And so I think technology is part of the solution, but if you don’t understand the anthropology and the history of your organization, you cannot create a sustainable solution. When I left Yale, I had said, “This thing succeeds not on this really generous endowment, but the people who are here maintaining it day to day.” They’re the ones who are connecting between students and alumni and the administration and faculty and the entire ecosystem.

And that’s, I think, what we’re missing in a lot of our legal organizations is those connectors, like the lattice and the people who know how to share information with the right folks, who see who’s missing in the communication cadence, who didn’t inform a process but should have because they’re sort of in the weeds even if their title doesn’t show it. And we’re beginning to see that with AI. We’re beginning to see it as we try to automate different systems and it doesn’t work in the way that we thought it would work.

Tom Mighell:

And we’ve got more to talk about, but we need to take just one more break. We’ll be back after a short break to hear from our sponsors.

Dennis Kennedy:

And now let’s get back to the Kennedy Mighell Report. I’m Dennis Kennedy. And I’m

Tom Mighell:

Tom Mighell and we are joined by our special guest, Anastasia Boyko. We’ve got time for just a few more questions. Dennis.

Dennis Kennedy:

So to follow up what you were saying, and this would’ve been great for my students to hear, because we talked about this a lot in my class, is how would you encourage today’s law students and new lawyers to find career paths in I would say the non-traditional careers in law in general, whether it’s legal tech or otherwise. And how would they start doing that? Because a lot of them say, “I go out and I look at the postings and they’re asking for somebody who has 10 years in generative AI experience to do this. ” And I don’t meet those qualifications. I go, “Well, basically no one does. So just apply and network and things like that. ” But how would you encourage these students today to really go out and try to find career paths that work for them?

Anastasia Boyko:

Yeah. So the guidance I got as a law student was I was given a book from the 80s called A Thousand One Things to Do with Yield Law Degree, which was a little out of date for my needs. I also had a bank of alumni I could reach out to a few dozen people and I tried to find people who had done something non-traditional to see how they had done it. I think a lot of law students took that sort of scavenge approach to try to figure out, right, who else has done something? Does this seem interesting to me? Luckily, we have much better resources now. I think many law schools have better alumni databases where you can get a better sense of who’s doing what and have connections with them. There’s a new group called Extraudicata that just got started that’s focusing on non-lawyer careers for lawyers.

Reframe lawyer that Ben Cheraboga has started has been talking about how to pivot your legal experience into an AI tech adjacent role. So there are a number of leaders who are putting together pathways for law students to learn about and young lawyers to learn about and those are great. And I talk to a lot of people who are trying to pivot out of their career and the first piece of advice I give them is you have to figure out who you are. It is the work most of us avoid as type A overachievers who are trying to do a bunch of accomplishments to send a message about how successful and talented we are to everybody else. And yet oftentimes we probably still feel empty because we haven’t done the reflective work of about what am I passionate about? What am I excited about? What do I want to spend my working hours on?

How much money do I need to make? What do I want to do for money? There are different things that maybe you want to volunteer your time versus actually do it as a career. And so it takes some time to start writing down for yourself, what tasks have I enjoyed in previous roles? What tasks seem to drain my energy that don’t really work for me? I tell everybody to take the StrengthsFinder assessment from Gallup, which gives you a sense of your top five strengths. It gives you a sense of where those strengths are optimized in certain roles. It gives you the blind spots that are associated with those. I did mine and it told me, “Don’t be a lawyer.” I mean, every assessment I’ve taken has told me not to be a lawyer and that would’ve been good to have earlier on, but I think I got a lot out of my legal education and I learned how to think and I learned how to approach the world in a completely different way.

I think a lot of people who go to law school aren’t suited for the current options that exist within the legal profession. They might be able to find those in a boutique or a really great mentor or in a practice area that is particularly unique or interesting, but you have to figure out what you’re about to, again, to be intentional and deliberate in the choices that you make. So if you choose a firm just because it’s prestigious because your classmates said it was prestigious, but you don’t know the difference between litigation or corporate, take some time, take some time, right? Take a beat, do some more research, use the tools out there that help you understand what those practice areas are, the nuances that exist within those categories, what life might be like in a non-for-profit versus a private law firm. All of these things deserve your attention because it’s your career.

And the more you get to know yourself, just like I said, I Goldilocks because I got more information about myself. I don’t like being in a firm spending all my time with paper. I like to read and I’m curious, I’m an intellectual, but I need to be interacting with people. I need to be in that kind of dynamic environment. So my soul dies if I live in my office reading text disclosure. And for some people, they love it, right? Their soul is really happy in that dynamic. And so because everyone is different, you really do need to spend that time at all points in your career to assess what it is that you’re uniquely drawn to and where your unique set of skills is particularly applicable.

Tom Mighell:

For our last question, this is our selfish question, which is who are you listening to these days? Who are you reading in legal tech? What are the voices that if we were to bring on new guests to the podcast, who would you recommend that we invite?

Anastasia Boyko:

Yeah, I have a little cadre of folks who are pushing against the tide. So my friend Owen McGran, I think writes with a deep philosophical bent to what’s happening with AI and that legal profession. My BFF cat moon is our all time provocateur and pushes to ask whether we actually think that we have choice in this. We are so much more autonomous than we think in this big change that’s coming in AI and she always challenges me to think differently. And my dear friend, Libby Clark, who has been consulting with companies and executive teams about how to think about the future of their organizations, former GC, a former partner who thinks about the law as that kind of ecosystem and the power dynamics there and what’s going to be happening with the future. So I would find those people and what they’re writing about on LinkedIn and on their Substacks and really challenge a lot of the mainstream ideas that are being fed to us about what this technology means.

Tom Mighell:

We want to thank Anastasia Boyko for being our guest on the podcast. Anastasia, tell our listeners where they can learn more about you or if they want to get in touch with you, how to do that.

Anastasia Boyko:

Yeah. I mean, I live on LinkedIn. It’s my professional SIM. So you can always find me on LinkedIn. I write every day, sometimes more than once a day. You can always reach out on LinkedIn message and I am always excited to talk to people who are interested in all of these unique ideas.

Dennis Kennedy:

And thank you so much, Anastasia. You’re fantastic guests. Great information, great advice. I wish I would’ve had you in to as a guest speaker to my students this semester. As usual, so many topics to discuss and so little time as always, but I love talking systems. So it’s great to hear your perspective on that. But now it’s time for our parting shots, that OneTip website or observation you can use the second the podcast ends Anastasia, take it away.

Anastasia Boyko:

So here’s an exercise that I tell everyone to do, which is on a piece of paper, write down what you think your principles and values are in your life. What are you about? And at the end of the day, gauge if the activities that you did during that day align with those values.

Tom Mighell:

Short and sweet. I struggled this week to find a parting shot. And so I saw a headline that caught my eye that I just wanted to bring up. And the headline was, if you’re using Windows 11, you don’t need antivirus software anymore. And I thought, okay, let me dig into that a little bit more because it feels not right. And so I did some of the research and it says, yes, right now Microsoft Windows 11, not any other earlier versions, but Windows 11 is secure enough that you don’t need an independent third party antivirus software as long as you don’t visit sketchy websites as long as you don’t do this. And it gave a list of about six things that we all do or we all do by accident even. And not that we’re trying to do it, we never know what’s going to happen.

So I think that my parting shot is if you saw that headline, please pass on by that headline and think about it more. I don’t know that Windows is the all end all for that. And I think there are a lot better tools out there to help with that.

Dennis Kennedy:

I wanted to react a litle bit to Anastasia’s thing because I’ve used coaches over the years and my current coach and I have been joking how the hardest thing when you go to a coach is they ask you these questions that are really tough, like, “What are my values?” That sort of thing. And so people just scares people off a little bit. But what you can do with AI, you can ask AI to be your stand-in and suggest what your values and principles might be and give it some background information and then you can edit it because it feels really safe and then it’s done some work for you go like, “Oh no, that’s not me. That’s not me. ” And you end up with actually something instead of feeling daunted by the whole process. So my party chat is we all have at least one piece of software we pay for, but absolutely hate using or dread using, don’t even use.

So before you give up on it or complain to your IT committee, spend just 10 minutes looking, doing a search for a product evangelist for that software or a recent tutorial video from the vendor. And what you find is that we’re often frustrated by a problem that a new feature has already solved. Tom, this goes back to the 60 tips episode we did. There’s already a solution out there and that if you find that one evangelist or one video, it can show you the why behind the how and that can completely change your workflow for the better.

Tom Mighell:

I don’t know. Sometimes I feel like I am like that so I can just go find something else new to play with. So I would want to do that instead. All right. And so that wraps it up for this edition of the Kennedy Mighell Report.

Dennis Kennedy:

A big thank you to the Legal Talk Networking team for producing the show. You can find the show notes and transcripts on the Legal Talk Network website.

Tom Mighell:

If you like what you hear, please subscribe to us on your podcast app of choice and leave us a review.

Dennis Kennedy:

You can also connect with us on LinkedIn with your questions or share your thoughts about this episode.

Tom Mighell:

And so until the next podcast, I’m Tom Mighell.

Dennis Kennedy:

And I’m Dennis Kennedy, and you’ve been listening to the Kennedy Mighell Report, a podcast on legal technology with an internet focus since 2006.

Announcer:

Thanks for listening to the Kennedy Mighell Report. Check out Dennis and Tom’s book, The Lawyer’s Guide to Collaboration Tools and Technologies, Smart Ways to Work Together from ABA Books or Amazon and join us every other week for another edition of the Kennedy Mighell Report only on the Legal Talk Network.

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