Hello listeners, welcome back to Behind the Bio, LISI’s podcast where two lawyers talk about turning points in unusual careers. I’m your host, Julie Owsik Ackerman, and my conversation with Jen Leonard left me curious and excited about AI, and lots of other ideas. We talked about using human-centered design in the court system, how generative A.I. could expand access to justice, and Jen’s new venture Creative Lawyers, where she works with leaders to help legal teams thrive in our ever-evolving future. Here is Behind the Bio. I know you’re going to enjoy this one.
Julie:
Welcome to Behind the Bio, our series that interviews a different lawyer each month to talk about Turning points in their career. I’m your host, Julie Owsik Ackerman, and I’m really excited to introduce today’s guest. Her name is Jen Leonard. She has had a really interesting career journey and has just started this new chapter, so hot off the press mews, and I’m really excited to talk more about it. We’re going to hear about working in private practice, working for the city, working at a law school. I mean, you really have covered the gamut of legal career options, which is so cool.
And then this new business, which sounds… Really am truly fascinated by what you’re up to and definitely want to hear more about that. So welcome Jen.
Jen:
Thank you so much, Julie. It’s a pleasure to be here. Thank you for having me.
Julie:
Oh my gosh, I’m so glad we can work it out. So let’s see. So as I said, we’re going to talk about the turning points and then a couple fun questions. And that’s what we’re going to do. Sound good?
Jen:
Sounds terrific. I’m excited.
Julie:
All right, great. So let’s get started. I had asked you to send me a couple turning points before the interview. And the first one you had said is leaving your private practice to become, I think you were the chief of the legal department for the city of Philadelphia. Is that right?
Jen:
I was the chief of staff to the city solicitor. So she was the head of the legal office. And just to give a little bit of context for what the office does, I think that office in particular, which is called the Law Department, tends to be a little bit under the radar as compared with the District Attorney’s office, for example. Everybody knows the DA’s office, which handles all the criminal matters in the city of Philadelphia. The city of Philadelphia’s Law Department, by contrast, handles all of the civil legal matters that confront a city, from litigation, to labor and employment issues, to civil rights issues. We represented the police department, the prisons department, adult health and behavioral health departments as well, the Department of Human Services, which handles all the foster care and adoption proceedings in the city. Real estate development, pension work. I mean, legislation and appeals, really runs the gamut. But I think a lot of people don’t know about the Law Department in the same way, maybe because there’s not a Law & Order version of a city Law Department.
But I met my husband there, and he had the job before me. I was chief of staff, he was chief of staff to the former city solicitor, and he described it as being an emergency room lawyer. You just came in and you had no idea what was coming through the door that day. It was always interesting, and you had to figure out how to handle it. And I think that’s the best way I could think of to describe that job. It was the coolest legal job I could imagine.
Julie:
And what were you doing before that job?
Jen:
So I was a litigation associate with a Center City law firm, Montgomery McCracken. And before that, I clerked for the Pennsylvania Supreme Court right out of law school.
Julie:
Oh, you did?
Jen:
I did, I did. And that was a great experience too. It’s really interesting because you don’t know how different experiences in your life will relate to later experiences, and maybe we’ll get to this. But I am really passionate about attorney wellbeing and have taught for the last five years a class on the connection between wellbeing and ethics. And in my very first job out of law school at the Pennsylvania Supreme Court, I was my justice’s liaison to the disciplinary docket, and got to see a lot of the things that ended up getting lawyers into trouble. And at that time, that was the early 2000s. People really weren’t using vocabulary like wellbeing, burnout, disengagement, all of the things that we talk about now, which is fantastic. But those were the actual things in many cases that were leading lawyers astray. So it was really interesting to have that early perspective and then be able to build that into the content that we talk about with our law students as they’re getting ready for practice.
Julie:
Yeah, I noticed that course description somewhere in your bio, and that’s really interesting. I had never until that moment, thought about the connection between those two things, but makes sense, right?
Jen:
Yeah. I hadn’t thought about it at all maybe until we had been presenting the wellbeing content for a while, and it occurred to me when I was reading some of the materials that that was exactly what I was seeing. Because as your audience will know, as you will know, one of the things that the state Supreme Courts take most seriously is mishandling of client funds. And that sounds like maybe it wouldn’t be a well-being issue. But in fact in many cases, because of a drug dependency, or just because of general inability to manage your practice because of wellbeing issues, can lead lawyers to mishandle client funds. So it actually is really inextricably linked to our well-being and mental health.
Julie:
Wow. Yeah. My father-in-law was really involved in starting in New York, the lawyers assisting lawyers… I forget what the title is, but the lawyer recovery movement in New York
Jen:
LCL, Lawyers Concerned for Lawyers?
Julie:
Yeah, so that’s near and dear to my heart and-
Jen:
That’s amazing.
Julie:
Yeah, it’s like how tied those things are together.
Jen:
That’s fantastic. I actually have a personal struggle and journey with well-being from the time I started law school. I was always a really happy, positive, high-achieving student in college and everything before college. I think I was very much a baby. When I started law school, I went right through. So I think I was actually 21 when I matriculated, which my stepdaughter now is 21. So I see her and I see how young she is, and law school really threw me for a loop. It was just such a different learning environment.
And even though now I would say I’m sort of introverted and extroverted, I’m very much introverted by nature. So Socratic method was really difficult. The pressure around exams was something I hadn’t experienced before.
I think in the end, the good news is that now, that conversation is much more open, and we’re developing all this education around it. But at the time, people didn’t talk about it. So I assumed I was the only person that struggled with anxiety and depression in law school and then in private practice. Turns out, according to all research, it is very much a lawyer’s problem and our profession’s problem.
So even though it was difficult, once I started working with law students again later when I was at the law school and started seeing them… And gosh, they’re so unbelievably talented. And they would sit across from me. I was a career counselor at the very beginning of my time at the law school, and they would say things that I would say to myself. “I’m not as good as everybody else here. I’m not going to make it. I’m not going to get the kind of job that I thought I was going to get.”
And it actually just broke my heart to hear them say that, because I could see how unbelievably talented they were. And because I had the wisdom of age, I guess, I could see that this was just going to be a blip. But I also know how real that feels. So it was very fulfilling to have the chance to build more integrated content in the curriculum itself, to help students understand that they’re not alone and that they can improve and achieve everything they came to law school to achieve.
Julie:
That’s so great. Yeah, I can relate to a lot of what you’re describing. And I think also, people who get to law school are pretty high achieving, I think we could say that. And I think for me, part of it was feeling so challenged in a way. Not that school was always easy. It wasn’t, but I always had excelled at school. And then all of a sudden it was this whole different method, this whole new way of training your brain, and not getting any feedback until, the end of your first semester is bananas. Just all of that is so anxiety-producing. Right?
Jen:
The feedback thing is the hill I will die on around legal education because I think what you’re experiencing reflects my experience that before law school there was a formula that I could follow. And as long as I did that, I knew that I would be successful. But a lot of that was formative feedback through quizzes, through writing assignments, through mentorship with teachers and professors.
And law school, of course, is completely different from that. And I know we’ll talk in a little bit about generative A.I., but one of the things that I’m excited about and would love to see developed is more generative A.I.-enabled formative feedback for 1L students so that… It is very difficult as a doctrinal professor to be publishing scholarship and be giving formative feedback to everybody. But the complete lack of it I don’t think helps the students in the end, and therefore, it doesn’t help the profession.
And so I think there are real possibilities for training A.I. on the specific preferences of a professor, so that any student can do it on their own time, at their own pace, as frequently as they like. And I think that will help lower some of the anxiety, and also promote more diversity and inclusion in our incoming classes.
Julie:
How do you think it would help with the diversity aspect? That’s interesting.
Jen:
I think one of the laudable changes in legal education in the last decade or so has been a really intense focus on recruiting diverse classes in every sense of that word. People who are first generation from low-income backgrounds, racially diverse, diverse by gender, although gender is something that we’ve actually achieved fairly strong results on for some time. LGBTQ+ communities.
So we’re bringing people from all different backgrounds, lots of different undergraduate experiences. I know when I went to law school at Penn, the number of undergraduate institutions represented were not as voluminous as they are now.
And that’s amazing. I think that’s exactly what the profession needs. But just because we’re bringing in lots of diversity, doesn’t mean that we’ve set up systems for everybody to succeed.
So if you’re a student who comes in and you know lawyers in your family, or you’ve come from a particularly rigorous academic background that prepared you well for law school, you are sort of unfairly advantaged compared with some of the students who are coming in that we want to be contributing to the profession.
And so if every student who’s coming in has the opportunity to learn on their own or in conjunction with a professor who’s helping them understand how the generative A.I. is giving them feedback, I think that could go a long way to providing tools to students who otherwise don’t have access to some of the same advantages. And that I think would help over time.
And I also think this could help in firms as well, with incoming associates being able to learn from A.I.-trained feedback that is specific to the partner or the senior associate you’re working for. And maybe that’s a conversation we haven’t yet gotten to is the connection between DE&I and generative A.I. We’re focused a lot on the bias part, which we certainly need to be focused on, but I think there are also upsides to it.
Julie:
Yeah. And because that also… I mean yes, it guarantees that students can have and associates can have access to that feedback, but also takes away that barrier of if somebody doesn’t look like me, or if I don’t feel comfortable asking for that feedback. There’s some of that unconscious bias that feeds into these inequities. And the idea that AI can help to level that playing field, that’s awesome.
Jen:
Absolutely. And there’s great research by a good friend of mine, Heidi Brown, who if you haven’t spoken with Heidi, you definitely should. She’s amazing. But she’s written a book called “The Introverted Lawyer.” She’s written several books about lawyers, and lawyer personality, and legal education.
But she talks about how advantaged extroverts are in a legal educational arena. And so the combination of extroversion and being more connected to professional networks I think leads some students to be much more comfortable approaching their professors or approaching a partner in a law firm and asking questions than a lot of other students who either don’t know that they should be doing that or don’t want to lean into any biases that are preexisting.
Or in my case, they just feel so overwhelmed by the material and confused by it, that they don’t want to betray how naive they feel in coming in as a first-year asking what seem like silly questions. Which again, with the benefit of age and time, you realize none of these questions are silly because it is also complicated, but you certainly feel that way when you’re 1L.
Julie:
Absolutely. Yeah. Wow, that’s really cool. So we naturally got there anyway, but I do want to talk more about your work at the law school. So you left the city and moved over back to Penn, right? That’s where you went to law school, is that right?
Jen:
That’s correct.
Julie:
Yeah. And so tell us about the work you were doing there and a little more than what you’ve already said.
Jen:
Sure. So I was at the law school for 10 years, and I worked on two major projects while I was there. The first, the reason that I went to work at the law school, was to build its center on professionalism, which was a new professional development program for law students. And the reason I was excited to build that program, with others of course, in collaboration with my fantastic colleagues was because I found in practice… I would say I don’t have a lawyer’s mind naturally. I have skills and talents in other arenas, but I don’t think that I’m naturally a lawyer or a legal thinker.
But what I was naturally good at was building relationships, problem-solving, bringing together different types of people. And by types of people, I mean people on the client side, people on the legal side, having more collaborative conversations, and figuring out what the client’s goal actually was and how we could get them there.
And we weren’t really teaching much of that content and those skills in law schools. And all the way back to 1992, there was the famous MacCrate Report from the ABA advocating that schools be teaching more of these skills. And to its credit, Penn built this program, and I had the great fortune of leading it and thinking about what do new law students need to compliment their doctrinal skills and what they’re learning in their legal research and writing courses.
So I got to build programs around executive communication, certainly around some of the well-being things that grew over time, but how do you manage yourself? How do you manage a project? How do you manage your time? How do you build relationships with clients? How do you navigate inner office dynamics and politics? How do you grow your career? So all of the things that are really the more human elements of becoming a lawyer that are not explicitly taught is the first program I built with others.
And in that time, I also was able to start teaching in law school, which for me was very funny, because I just felt like I was such an inept law student, that the idea of me teaching law students was so disorienting to me. But I’m from a family of educators. Actually, my dad was a Philadelphia public school teacher for 40 years. Yes. My husband is a public school teacher, so yeah.
Julie:
In which district?
Jen:
Philly, my husband is, yeah.
Julie:
Oh, is he?
Jen:
Uh-huh.
Julie:
We’ll have to talk more about that. That’s amazing.
Jen:
And that I think, I don’t have a lawyer’s brain, but I think I have an educator’s brain. And I think that I really love trying to come up with different ways to help people understand how to grow, and nurture their own minds, and learn content of course, but also learn skills that will help them become lifelong learners.
And I started teaching a law firm, business strategy class, actually. And I started teaching in 2013. So this was right on the heels of the great recession. And we would have guests come in and they were all fantastic, but they would constantly talk about how this was this inflection point in legal, and law firms were really good at change because corporate counsel was pressuring them.
And after I taught the course for about four years, it just sounded like the same thing over and over again. And I wasn’t seeing significant transformative change in the way that law firms worked. And then at the same time, I was becoming more educated about the civil justice crisis, and how lawyer-centric legal systems are, and how they are not designed really for the average person to navigate, even though the average person is navigating them entirely on their own.
And so that combined with my personal experience in emerging research on the lawyer well-being front made me really feel compelled to think about how we could redesign everything that we do, from the first days of law school to the way that we deliver legal services, to the way that we leverage technology, to the way that we take care of ourselves and others around us. And the way that we welcome other disciplines into our conversations, which is something structurally we’re really not set up to do.
So in 2018, our dean asked me if I would lead a working group to think about what innovation in a leading law school would look like. And all of that work, which was a phenomenal collaborative experience in and of itself, ultimately led to the creation of the Future of the Profession Initiative, which I had the great honor of leading for the last four years. And that was focused on teaching students about a changing profession, leading new conversations with people who are out in the profession so that there’s a deeper connection between us and the people who employ our graduates, and then building transformative projects to try to change legal systems to be more human-centric. So that was a lot, I know. But that’s essentially the shape that my work took over the 10 years that I had the great opportunity to spend at Penn Carey Law.
Julie:
Wow. Can you tell us about one of the projects that you were working on towards the end there?
Jen:
Sure. So another class that I started teaching, because I learned about this framework from my good friend Mary Ann Leary, who leads the innovation work over at Penn Nursing, is design thinking and human-centered design. And I got really excited about design thinking, because it’s not the way that we’ve designed our systems, and it starts with the people that we’re trying to serve, and then works from there to develop ways to do that.
And so I started teaching a course on human-centered design, and that course sort of became connected with a Future of the Profession Lab, which we launched last year, which my fantastic colleague Jim Sandman leads. He is president emeritus of Legal Services Corporation and a staunch advocate for reform of legal systems to respond to civil justice crisis.
But that lab really draws from the class and connects to the class in its focus on human centricity. So last semester, we worked with Judge Matthew Wolf of Philadelphia’s municipal court in having our students go and visit municipal court and see what the experience was like. Not for the lawyers in the court, but for a person who has been summoned to court because they’re in debt, either consumer debt or medical debt. And they’re navigating this system all on their own. And municipal court is supposed to be the people’s court, so it’s supposed to be self-navigable, but our students spend time there. And they looked at some of the ways that environmentally, people who are self-represented already feel outmatched when they get there, because they see lawyers and judges at the front, and they’re in suits, and they’re talking to one another, and it’s a fraternity. And you already feel like you’ve lost the second you walk in.
And so having the students interview litigants, interview attorneys from Community Legal Services, interview the judge, and then think about what could this courtroom look like, and what could this experience look like if we stopped looking at the legal participants, the legal professionals, and started by looking at the self-represented litigants? So that work is underway, and Jim and our other colleagues are continuing to build projects to be more human-centric in self-represented litigate situations.
Julie:
Wow. Yeah. Wow, that’s awesome. Yeah. So part of my legal work was I worked at Catholic Social Services representing immigrants before law school, and then I did a lot of immigration law in my career.
So add to whatever challenges there are, language differences, cultural barriers, not having legal status in this country. And of course, there’s no right to an attorney in immigration court, which is civil proceedings. So I really see the need for that, making things more human-centric, and just think it’s awesome.
Jen:
Yeah. And I mean, if you think about your experience at law school and the introduction to the profession, I know my colleagues and I, my peers and I, we used to love learning Latin, and having all sorts of fun with puns, and all the different concepts that we were learning. But when I look back on it, what you’re really doing is you really are being enculturated into a fraternity of people who know the lingo, and they know the jargon, and they’re having fun learning it.
But what is the outcome of that? It’s we’re becoming more and more separate from the rest of society, very much intentionally so, whether we think about it that way or not. And on another podcast, we could unpack whether there should be two sets of civil procedure or two sets of rules of professional conduct. One to govern the really sophisticated corporate clients that large law firms serve, and another to govern the rest, because the level of sophistication and the level of knowledge is obviously very different. But the entire profession really is governed by one set of rules.
So helping students at the outset understand that, it is challenging too, right? Because they’re trying to learn all the other things that they need to learn in law school. And so then trying to have them think about systems redesign is challenging, but I think they are the most primed to think differently because they don’t know anything else at that point.
Julie:
Yeah. They haven’t been indoctrinated yet.
Jen:
That’s right. That’s right.
Julie:
And I’m wondering, just as we’re talking, if there’s a place for law schools and CLEs, dare I say it, to help bring this conversation to people that are already practicing. Because I feel like in law school, you’re just trying to get a foundation. But then once you’re out there it’s like, “I really wish I’d learned some of these things about running a business.” It’s like you don’t know what you don’t know until you’re there. And then once you are there, I don’t know what your experience with CLE has been, but mine is very mixed. I don’t know. It would be great to have CLEs that really bring these things to people who are practicing. Maybe they’re out there and I just haven’t found them. I don’t know.
Jen:
I think there probably are some. I think the challenge with CLE is it’s so self-directed, and it’s frequently something that we squeeze in when we can. And you get close to your deadline, so you’re just looking for something to fulfill your credits. But I think you’re totally right.
And the place where I’ve seen this in the most pronounced way is with the wellbeing content. We’ve done content for our students as well as our alumni. And frequently, the alumni receive the content in a more advanced way, I think because they have context around what we’re talking about. When you’re talking with students, they also receive it well because they’re in law school, but they haven’t yet practiced. So some of the things we’re introducing them to are not familiar to them yet.
So I think you’re right in the same way that trying to describe to law students how the systems are not well-designed, they don’t really know yet. But if you went in I would imagine to a group of lawyers… I actually find lawyers, even though there’s all sorts of research on how skeptical they are, and how reliant we are on precedent, and small C conservative, I think most lawyers recognize that the system is not well-designed for most people. But there’s no stakeholder really responsible for redesigning everything or looking at it differently. And I think if you compare legal with the healthcare industry, for example… And my colleagues on the healthcare side of campus would say that that is a deeply flawed system. But the involvement of third-party payers for medical services has led to some innovation and some efficiencies. In legal, we don’t have a driver forcing us to really be thinking differently.
And there’s not an awareness among the general public about the lack of access to legal services. So there’s a lack of outreach and a consumer movement around expanding access to legal services. There’s a lot of education and awareness raising, and then you need some incentives to actually drive change.
Julie:
Right. I love this, thinking about the big picture. Okay, so now let’s move the journey along a little bit. So you had this awesome, it sounds like a really good experience at Penn Law, Penn Carey Law. And tell me how that turned into this new venture that you’re embarking on.
Jen:
So for added context to the work I’ve done over the last few years, of course, we were doing all of this work during a pandemic where we were really disconnected from each other. Our project launched February 28th of 2020, so we were ready to hit the ground running. We were ready to do all this fantastic stuff on campus. And then two weeks later, we were just in the murky mess of Covid, and just trying to figure out what we could possibly do on Zoom to build a whole project.
And it was very frustrating and very difficult because of the constraints. But, one thing I’ve learned from my colleagues in the different parts of campus and innovation is that constraints really can drive strong innovation. And I found myself during the pandemic working with my colleagues, at the law school, working with my team, but also being introduced to all these people all around the world that I otherwise would never have met.
And I made fantastic friends with people like Rachel Dooley, who’s now the chief innovation officer at Goodwin. She and I bonded over creativity and the need for more of it in legal. And because we were sort of stuck in our houses, we had the luxury of sitting on Zoom calls and thinking about what that could look like over time.
And I was talking with corporate GCs, and law firm managing partners, and judges, and just this hugely diverse group of stakeholders. And because the profession has been so slow to change and because it was disrupted so abruptly, people didn’t know what to do or how to think about innovation.
And so I got more and more incoming inquiries from places that really wanted help with educational content and workshops, and some keynote presentations. And I loved working with individual firms and individual GCs offices to help them think through and do podcast recordings like this and talk about the issues. And one of my board members joked that in the role that I had at the law school, I started getting introduced to more innovators and entrepreneurs, which made me realize that I wanted to be more entrepreneurial and innovative.
And so like everybody else, I was doing a lot of introspection during the pandemic, and what do I want my life to look like on the other side? And what I really wanted was the freedom to be really creative, to build something… I like building is another thing I’ve learned from the professionalism program to innovation. And I wanted to build this new thing, this new venture that was entirely of my creation, and focused on all the things I care about in the legal profession, and expanding my ability to reach clients and reach everybody, and help work on custom tailored programs that would educate, inspire, get people thinking in new ways, and bring all of this great stuff that I’ve learned at Penn to the broader profession.
So I would’ve never thought of myself as an entrepreneur. I am the classic lawyer, conservative, risk-averse, rules-following people pleaser. But I don’t know, I felt like if I were on my deathbed and I didn’t try this, that it would be probably the biggest regret of my life. So as scary as it is, now that I’m doing it, it feels like the right thing to do. And I also feel like it might fail massively. And unlike in 2019, I’m okay with that in 2023. And I think that’s another change the pandemic created in me at least.
Julie:
Yeah. Well, I’m excited, really. Yeah, I’m inspired. I’m feeling really excited about this for you and for the profession. And let’s see, I did… There was something else. Two more things I wanted to ask about. One, which might be a little faster. I saw that you’re going to be offering or maybe are offering pause retreats for women lawyers, and I’m very interested in hearing more about that. Can you tell us about that?
Jen:
Yeah, absolutely. This I would say is my biggest passion project, and I’m going to start with a pilot version in early 2024 with people I know who are women lawyers who are mid to senior level. And I’m so fortunate to have amazing women lawyers in my life.
And what I really realized during the pandemic, I started this monthly group on Zoom called the lean in, lean out, lie down circle. And I stole it from Ali Wong, the comedian, because she has this whole thing. She doesn’t want to lean in, she just wants to lie down.
And I was talking with all these women in my life on Zoom, or over drinks, or when we were allowed out of the house. And everybody seemed to be saying the same thing. We’re basically in our forties now. Some people have kids, some don’t, but everybody was sort of like, “What does this all mean and what do I want to be doing with my life?” And then on other days they’d be like, “I’m just too tired to even think about what I want to do with my life. I just want to hang out and have fun.”
So I started bringing everybody together monthly, and there were about 10 of us. And we would talk about everything. I mean ranging from, “I need to update my resume, can somebody coach me on salary negotiations?” To, “I got this great coupon for discount wine and you guys should go get some.” I mean, anything that we could do to support each other during this weird time, we did.
But that sparked an idea in me that lawyers in particular, I think two things happen. I think one is you start down a very specific, well-defined path. And most of your peers also are headed down that path. And that path, the second piece of it is that path, especially if you’re in private practice… But that’s not entirely true. It’s in all legal practice, requires that you contribute all of your energy and time to practice, to your clients.
And that’s fantastic for everybody else. But what that means for us sometimes is that we don’t get a chance to hit pause, and we don’t get a chance to reflect on what we actually enjoy and what we don’t want to do anymore of.
And so I want to sort of blend those two experiences and knowledge, what I saw during the pandemic with what I know about the profession, and give people a chance to have two days even disconnected, not building time, to sit with other people and think about, “Where do I want to go for the next 20 years of my career?”
And maybe that’s building on what you’re already doing, or maybe I want to pivot to something totally different, because this is not what I want to be doing forever. And so I am really excited about that project in particular, and I could see it being relevant for law firm women’s committees. You could create curriculum that is designed for people who are staying within a firm and looking for leadership opportunities. And we know there are huge attrition problems for women in law firms. Or it could be a collection of individual lawyers who are looking to make a change or looking to be introspective.
So I’m really excited about that. I think in January, I’m going to recruit some very close friends to give me intense feedback on the experience so that we can make it stronger and then start offering it to the profession at large.
So any thoughts you have, if you want to be part of the pilot, you are welcome, Julie. I would love that. That would be amazing, amazing. I’m writing your name down now. You’re on the list. But what do you think? I mean, what excites you about that?
Julie:
Let’s see. I mean, a lot of things. I’m in a similar age. It’s part of my career as what you’re describing, and just the idea of, I mean, on a larger scale, what we’re doing now is taking the camera back to look at a bigger picture.
I think a lot of us, and I put myself in this group, have a lot of interests, and a lot of gifts, and a lot of skills. And you spend some time building, you get on a path and you stay on that path. And then at middle age, which I guess is where I am, you just start thinking about, “Okay, I’ve done all these things and they’ve been good, or bad, or whatever. And do I want to stay on this path or is it time to make a change?” And I think those questions have just been present for me for a while also. So I love the idea of gathering with other women in a similar state of mind, similar position, and just making some space for it. I think that’s a great idea.
Jen:
Same. And the thing that excites me when I talk with my women friends in particular… And maybe down the road if this becomes a thing, it wouldn’t just be women, because I certainly know all lawyers sort of have these questions, but my circle happens to be women at the moment. But what I find interesting is I have a good friend, and she’s highly successful corporate attorney in-house. She is moving her way through the ranks. She has no interest in leaving. She wants to put the pedal to the metal, metal to the pedal. She wants to keep driving forward.
And she’s equally interested in this work as my friends who are sort of like, “I don’t want to practice at all anymore. I want to become a novelist, I want to go back to school to become a teacher.” And that to me feels like, to the extent that I’ve learned anything about entrepreneurial mindset yet, it’s like you’re seeing this commonality across people who they do have a shared educational background, shared career background. But there are differences in what they want to do. But they all are craving the chance to get together with other supportive professionals and just to have time, like you’re saying, to explore their own interests.
And whether you have kids or not, but especially if you have kids. I mean, I think that that can fall by the wayside. And just like I hate to see my really enthusiastic, eager students show up on campus in August of their L1 year and feel really badly about themselves because they got a bad grade when they come to see me in January. In the same way, I don’t want to see my friends who are 45 and have two small kids, and they’re like, “I wish I could think of something different to do. I just can’t find the time,” not live up to the things that they’re capable of doing and are gifted to do.
At heart, I think what I want out of our profession is for people to have lives that are more aligned with the things that light them up over time, and not get to retirement and feel like, “It was okay, but I wish I had done something different.”
Julie:
Yeah. Well, I love it. I’m in.
Jen:
Yay. I’m excited. Tell your friends, send me names.
Julie:
I will.
Jen:
Please do.
Julie:
Okay. I’m looking at our time. I don’t want to take too much more of your time, but I do just want to make a little space to hear about generative A.I. because I think this is on lots of people’s radar, most people radar. And I know this is something you’re passionate about. So I guess just to focus us a little, if you could just tell people who may not know, what is generative A.I.? And what do you see as the opportunities and potential problems for the legal profession?
Jen:
Yeah. So I will start by saying I’m not an expert on generative A.I. I think very few people I know are. I will say I’ve spent the last nine months absorbing every bit of information I can to educate myself about it.
Generative A.I. is a subset of A.I. generally. And we all are used to A.I. in our lives, whether we know it or not. A.I. proposes shows that we watch on Netflix based on things that we’ve watched before. A.I. tells us how to get to the supermarket when we put it into our GPS in our cars. A.I. is everywhere in our lives. It’s infused all over, or auto-complete when you’re drafting an email.
Generative A.I. is different in nature and in scale. But in nature, it’s different because it’s not looking for patterns in existing data or existing behavior like Amazon guessing what you might buy next based on what you’ve bought before. It’s actually taking the information that it has, learning from it. And in response to human prompts, generating entirely new content, versus looking for patterns and proposing things from preexisting content.
And so for lawyers, as I’m sure everybody knows at this point, but for lawyers, generative A.I. really has the capacity to have profound impact on the profession. Because what we do is generate content based on legal research, based on the way that we write, based on putting together facts and combining those facts with the existing law, and generating opinions, or generating briefs or memos, or generating new transactional documents based on inputs.
And the reason I think generative A.I. has such capacity to impact the work we do is because our information, legal information is so perfectly primed because it’s organized, it’s written in a very uniform fashion, and it’s designed to be reused over time. It’s not proprietary. It belongs to everybody.
If you’re talking about in a law firm, you even have a further degree of susceptibility to impact because you have a document management system that has 20 years of the repository of all of your attorney’s work product.
So if I’m at the firm Smith and Reynolds, which I just need up, maybe there’s a firm out there, Smith and Reynolds. But I can search for all of the motions to dismiss that my lawyers have ever drafted, and I can train in A.I. on just my firm’s content.
So a lot of the concerns about the garbage in, garbage out, mixed quality of information goes away when you know that that information was created by your lawyers. And you combine that with trustworthy publications like West, and the Federal Reporters, and all the statutory documents that we have.
Those are two really trustworthy sources of information. And again, they’re uniform in the way that they’re written, by and large. So the combination of those two I think is really powerful.
In terms of the opportunities, I see so many different opportunities. We talked a little bit about the DE&I opportunities for training new lawyers, for training new associates. I think there’s a real chance that we could expand the pricing portfolio for legal services so that billable time becomes part of the portfolio, but not the only part.
And there’s so much fear right now in law firms around gen A.I.. But I think if we can get past this first chapter of it, we can see that the way that we’ve been working applies so many limitations on our ability to serve more clients, on our ability to lead lives of balance. What if we could do work more efficiently, do more of it for more clients, generate more revenue, and live better lives?
And then of course, in the access to justice space, I think there are huge opportunities because people no longer will need lawyers’ permission to access information. And we have been the gatekeepers for a lot of that. I would say we have not necessarily lived up to our obligation to society in a lot of respects there. And this is a game changer when everybody who has a cell phone can access their own information. And we want to be a part of that as lawyers, but I don’t think we want to be an impediment to people having greater access. There are certainly risks around all of it.
The thing that I think the most about is, how do we adjust the way new lawyers are formed? If the work that you and I trained on, which was boring, and laborious, and rote in many cases, but ultimately contributed to our understanding of a legal representation. If some of that goes away or a lot of it goes away, and if students are able to access GPT-enabled technology to help them write briefs and memos, and they’re no longer developing their skills in the same way, who’s responsible for finding out where the gaps are, finding out how to fill them? And who will pay for that training at the junior levels of practice? Because right now, the corporate clients pay for it in the private sector. And I think that will change very quickly.
And so that’s the tranche of the legal profession I’m most concerned about, most focused on, think the most about, and I’m trying to work through my company now to help firms and law schools think through what that means for them, and how we can get our arms around it and respond thoughtfully without fear.
Julie:
And I was thinking today that when I went to law school… And I don’t know if law schools still do this, you would know. We still learned on the books. We still went to the physical books in the library and had to look at… Oh my gosh, I’m blanking. What’s the word for checking citations?
Jen:
The shepardizing?
Julie:
Yeah. We did that in books, even though the technology was already there, but they wanted us to know how to do it. And I was thinking today how that seems absurd to me now. I don’t know if we still teach students how to do that. But the idea that you would go through all of that when you could just push a button, just helped me kind of think about what some possibilities might be. Because that might’ve been scary to generations before us. But knowing how much better that has made more efficient, who would ever want to spend the hours doing that anymore? Nobody. So if I can think about it that way, maybe I can be a little bit more positive and open-minded, instead of scared about the robots coming for our jobs.
Jen:
Totally. And I think that’s a helpful analogy, right? Any lawyer who’s a partner now has probably lived through some version of what you’re describing and the fear associated with it. Or if you go further back, email. Or I guess it’s around the same time, but how could we possibly put confidential client information over this system that we don’t know and we don’t trust? And of course, that’s how everybody does everything now.
Again, I think the nature and the scale of this is different, and I think it’s going to be messy for a little while. And one thing I think will change, at least in the short term, is that law school education, by and large, no matter which law school you’re recruiting a student from or going to, is pretty uniform. You know what to expect. And as an employer, you know what they’ve learned. And I think now, you’re going to see schools take very different approaches to how they integrate this content into their curriculum. And I think you’re frankly, going to see different levels of talent within law schools capable of keeping up with this in real time, capable of teaching it.
They’re already trying to teach so many complex things as it is, and you’re going to be competing as a law school against law firms who will be able to pay many multiples what law schools can pay their professors, to teach their associates the same things.
And so I think one downside of that or one challenge is there will be a whole new world of legal employers having to become more intimately familiar with the curriculum at each school that they’re hiring from, and going under the hood and seeing what they’re actually teaching.
On the flip side, I think to the point of the earlier DE&I conversation, it creates real opportunities for schools that maybe haven’t had the access to on-campus interviewing and the prime jobs in the market, because they’ve been boxed out. But what if they become the leaders in developing new curricular approaches that integrate this?
And Suffolk Law School is the prime example of this. Dean Andy Perlman at Suffolk has been leading the charge for at least a decade in integrating technology into legal education, and all of that work has built a muscle with his faculty around how you do that. And I could see that being a real advantage to Suffolk and schools like it who are able to respond to this more quickly than schools that haven’t had that component to their curriculum.
Julie:
Wow. So much to think about. Oh my gosh, I could talk to you for hours easily about this.
Jen:
We will at our retreat.
Julie:
Yeah, seriously. I hope I am on that list because I want to come. All right. Well, thank you so much, Jen, really for your time and for the work you’re doing. I find it interesting and inspiring. And I’m really looking forward to learning more. So let my listeners know, how can people find you if they want to learn more?
Jen:
Yeah, absolutely. Well, I’m on LinkedIn and I’m pretty active on LinkedIn. So please look me up and connect with me. You can also learn more about my company Creative Lawyers at creativelawyers.net, and my email address is just Jen, J-E-N@creativelawyers.net. So you can reach me through any one of those avenues, and I hope that you will. And I hope this conversation has been helpful for your audience, and I’m excited to really dig into the work of Creative Lawyers and help the profession transform in the years ahead. It’s really, really exciting times, I think.
Julie:
That’s awesome. Thank you so much, Jen. It’s been awesome talking to you.
Jen:
Same to you, Julie. Thank you so much for having me.
Julie:
Yeah, okay. Take care. Bye-Bye.
Jen:
Bye.
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