Can Law Firms Redesign Themselves for AI? Jen Leonard on "Unprecedented"

In this episode of AI and the Future of Law, Jen Leonard and Bridget McCormack are joined by Sharon Crane, president of Practising Law Institute, for a conversation about Jen’s new book, Unprecedented: Designing a Human-Centered Law Firm When Everything Is Changing. Together, they explore why law firm transformation is difficult, how storytelling can make change feel more accessible, and why collaboration, human-centered design, and practical experimentation matter in the AI era. 

The conversation also covers PLI’s AI competency framework, the value of business fables, the history of the Cravath system and the billable hour, how Jen used AI as a writing partner, and what the future of junior lawyer training might look like. 

Key Takeaways 

• Law firm change requires human buy-in. AI can generate plans, but people still have to align, lead, and execute them. 

• Storytelling can make transformation more usable. Jen’s book uses a fictional law firm retreat to help leaders see the human realities of change. 

• The current legal model is not inevitable. The Cravath system and billable hour emerged in specific historical moments and can evolve again. 

• AI can be a co-intelligence, not a shortcut. Jen explains how she used AI for research, feedback, ideation, and reverse interviewing while keeping the core drafting her own. 

• Junior lawyer training needs new models. As AI changes entry-level legal work, law schools, firms, and education organizations may need to collaborate on more flexible, experiential training. 

Final Thoughts 

This episode is a conversation about redesigning legal organizations for a world where everything is changing at once. Jen, Bridget, and Sharon make the case that law firms do not need to abandon what makes them valuable—but they do need to build new ways of learning, collaborating, and leading before disruption forces the issue. 

Transcript 

Intro + AI Aha! 

Jen Leonard: Hi, everyone, and welcome to the next episode of AI and the Future of Law. I'm your co-host, Jen Leonard, founder of Creative Lawyers, joined as always by the wonderful Bridget McCormack, president and CEO of the American Arbitration Association. 

And Bridget and I are really excited today. We frequently have guests that we don't know very well, and we get to know more about them. But today we have a guest that we know very well, and who is part of our collaborative effort to transform the legal profession, and also a partner in the success of our podcast: Sharon Crane, who is president of Practising Law Institute, which distributes our podcast and many other programs that we deliver. 

We adore Sharon. And just to give you a little bit of background on her wonderful credentials and experiences, as I mentioned, she's the president, currently, of Practising Law Institute, or PLI, which is a legendary nonprofit that's been keeping lawyers at the top of their game since 1933. She took the helm of PLI in 2020, and she joined from Davis Polk & Wardwell, and is only the second woman ever to lead PLI. 

She's a Columbia Law grad with an undergrad degree in psychology from Georgetown, a corporate lawyer turned executive who spent her career thinking about how the profession learns and adapts. And under her leadership, PLI has certainly leaned hard into the future. They have launched an industry-first AI competency framework and a new Innovation Council that I get the opportunity to chair, and I'm really grateful for that opportunity. 

And she's also the reason this conversation today is a bit of a family affair, because we are going to talk about an upcoming book that I had the chance to author in collaboration with PLI’s fantastic publishing team. 

So we're thrilled to have you here, Sharon. Finally, welcome. 

Sharon Crane: Well, thank you. I am so excited. I get to be a guest and not just a listener. This is the one podcast that I never miss, so I'm so excited to be here. 

Jen Leonard: Thank you so much for being here. And as you know, because you listen to the podcast all the time, we start with an AI Aha! from our guests — something you're using AI for that you think is particularly interesting. And we would love to hear yours, Sharon. 

Sharon Crane: So this is definitely — I was a little nervous about this because your guests, I think, have easily leaned much more heavily into tech and have some really cool ones. But for the average person, I'm going to give you the two that I just started using. 

One is that recently, for a presentation, actually for our competency framework, we wanted to let the organization know a little bit about the framework that we released out into the legal industry. And we actually used NotebookLM. We put the framework in there and asked it to produce a short video to explain the basic tenets. And it did a fabulous job. 

It was a four-minute video, and it went through the basic tenets of the competency framework very clearly, concisely, and with accompanying video and illustrations. And I think it actually went over way better than it would have if we were just describing it ourselves. So that is an interesting use case that I will use maybe for other presentations that we have. 

And on a personal note, I've been using ChatGPT to be my health coach, counselor, and much more. I basically write in what I've eaten in the day, what exercise I've done, and I have it suggest what I should do, let's say, for lunch or for dinner. And then when I slip up, which I often do, it is there to say, “Don't worry, one day doesn't move the scale too much. Try this next tomorrow.” 

So it's been both like a coach and motivator. It’s very easy because I just type it in very quickly. So, a professional one and a personal one. 

Jen Leonard: Love that. And we love NotebookLM. 

Bridget McCormack: Yeah, NotebookLM has been really amazing. If you're working on something and you want it to really put it together either in a deck or in a video, it's a pretty amazing tool. It feels to me like it gets better and better all the time. So that's a great use case. 

And the personal fitness coach or personal nutrition coach, or all of the above — as Jen knows, I've been doing that forever with these tools, and I kind of use them all. And lately, I'm really into Gemini for this. Adding sleep to the mix and other sort of metrics that I think contribute, that are all kind of interconnected. 

And then I'll ask it at the end of the week to give me a review of where it thinks I might want to focus next week. It always puts it in a really positive way. It's not like, “Wow, you were a hot mess with your French fries this week.” But, you know, I find it pretty useful. And you could just talk to it as something happens. So it's a great use case. 

Jen’s Book, Collaboration, and Building New Superpowers 

Bridget McCormack: Jen does not like to be the center of attention, but she has written a fantastic book, and I'm really excited that PLI has published it, and that so many people across our profession are going to get to benefit from it. The title is Unprecedented: Designing a Human-Centered Law Firm When Everything Is Changing. 

The book tackles the question every legal team leader I meet is struggling with right now, which is: how do we take what we've done well for a very long time and reinvent it when generative AI is shifting what our stakeholders care about, what our clients care about, what our partners care about, how work happens, and all of the economic models that have worked for the last couple of hundred years? And all at once, we're supposed to figure this out. 

And it's kind of overwhelming, especially on top of running a successful business to begin with. Right? That's overwhelming enough. So it's an awful lot. 

And I can't tell you how many legal leaders I've talked to who said, “Look, I just haven't figured out what to do about it. I care. I know it matters. I know it's important. But with everything else going on, I don't know. I just haven't had the time to devote to it.” 

And so we have a great answer for them now: this amazing new book. 

And what's cool about the book — there are many cool things, and we're going to talk about those — but what makes it different is also the way it approaches this set of hard questions. 

Instead of your typical management text, it's told through a story, which is Jen's superpower. Well, she has a lot of superpowers, but one of them is definitely figuring out how to tell a story that holds a lesson and impacts the reader in a way it would have been hard to do if you just read the lesson itself. 

And the story is a fictional week-long retreat that a law firm is having. It has amazing characters, and it brings the human realities of change right to light on the page. There's a lot of uncertainty and resistance, and the courage it takes to build something together. 

And it's genuinely usable. Jen weaves in practical tools like reflection questions, frameworks, and agendas. There are all kinds of use cases built into an actual blueprint — not just inspiration. 

Sharon Crane: So this is one of those stories where it's always helpful, if you're a networker, to keep in touch with people. 

I actually met Jen maybe 10 or 15 years ago, when I had stopped practicing law and I was the head of recruiting at a law firm. She invited me to come speak to her class at Penn Law about hiring and, actually, the law firm business model. That was 10 or 15 years ago. 

And then we reconnected when I came to PLI. Through Jen and her ventures with Creative Lawyers, she has introduced me to some amazing people, like you, Bridget, and others. 

And what's been great about our collaborations, particularly in the age of AI, is that we are all learning, and things are moving faster than any one person or any one organization can possibly stay on top of. 

So I was really pleased to be able to work with Bridget and the AAA as another nonprofit organization, and to find a like-minded CEO who was willing to experiment and break things. And it's easier to do it with company. 

So I think, in this world, it's so much easier to collaborate and learn from each other's successes and failures, and help each other get to the point, because it's moving too quickly for any one person or organization to handle. 

When we first linked up, I think AAA had already been building, with Jen, the Law Firm AI Strategy Program. And when I heard about it, I said, “Oh my God, this is fantastic. Our members would love this. Can we somehow collaborate or license this from all of you?” 

And in the spirit of collaboration, you both said, “Yes, that would be great.” And so we released that, I believe, last year. 

And because of that, and its interest and success, we're looking to have another program that hopefully will come out later this fall. We'll start working on it this fall. 

It's just one of those things where you start to talk to like-minded people, get to meet other people who have similar ideas, and you can just expand from there. So it's been a great collaboration, and I’m happy that we were able to reconnect, Jen, and that you were able to connect me to other people as well. 

Jen Leonard: Well, I know one of our frequent guests, Jae, has told me that her favorite word in the English language is “encourage,” to literally give courage to other people. And I love what you just said, Sharon, about it being easier to try to drive change when there are other people in their own organizations trying to drive change, because it can be a lonely experience. 

But also, for me, I'm in a very different kind of organization from both of you. But you have both encouraged me to really build something unique that aligns with my values and the things that I want to build. And so I'm grateful to both of you for the encouragement, and I'm so excited about all the different projects we get to align around. It's really great. 

Bridget McCormack: In some ways, Sharon and I are both leading these very storied nonprofits that have been around for a long time, and we have big teams and we're in place. And you and your team operate like a startup. Right? 

And so I think it’s pretty exciting for us to have you and Marielle and your team involved in some of these projects that we're doing together. I do think it makes us all better to have a bit of a mix of contributors. 

Jen Leonard: It was really kind of you to say that my superpower is storytelling. I'm happy to have an actual legit superpower, because I used to say that my superpowers were parallel parking. Like, I could parallel park a car into any parking spot as long as it will actually fit. 

This feels like growth, that I have something that might actually help people a little bit more. 

Bridget McCormack: I mean, I don't know. The parallel parking skill is pretty legit. That's pretty badass, I have to say. 

Sharon Crane: But I will say — and I'm going to connect that to AI a little bit — I just did an excellent parallel park the other day, and people were around watching, because people always get freaked out, like, “I don’t want to parallel park where people are watching.” And there were people on the sidewalk, and it was perfect, I have to say. 

But I was like, this is a skill that's not going to matter anymore, because with Waymo and self-driving cars, in the future people will probably not be having to parallel park. So I'm glad you have another superpower, Jen, because mine may be going the way of the dodo bird. 

Jen Leonard: And isn't this the lesson? We have to be building new superpowers, or we could be obsolete. 

Bridget McCormack: I mean, we just wrapped the podcast. That's it. That's a wrap. Right? 

Sharon Crane: I mean, that was the moral of the story. 

Jen Leonard: Yeah. Disrupt yourself before you’re disrupted. 

Bridget McCormack: Great to see you guys. Have a good rest of your Monday. 

Bridget McCormack: I want to talk about your book, Jen, because it's amazing. It's a really important contribution. I think so many people are going to buy it and use it because it's so useful. 

Sharon and I have lots of questions for you, but I'm sure this will turn into more of a conversation. 

Why the Book Is a Business Fable 

Bridget McCormack: Let me start with the way you put it together as fiction — this made-up firm. I assume it's made up. You can tell me if it's based on a real-life firm. But unlike a traditional business book, it's just more fun to read. 

By setting it up as fiction, I have a sense that your characters allow the reader to be pulled in and learn in a way that's harder with a straight how-to prose. 

Jen Leonard: Yeah. So this was actually the third structure of the book that I landed on. 

The first was a very traditional business book. I was going to lay out the issues in the legal profession and then introduce different frameworks that law firms could use to respond. So it would be design thinking and innovation tournaments, and then some ones that I wanted to learn more about, like blue ocean theory and nondestructive creation. 

And I just started writing it, and I thought a couple things. One was, why would anybody want to read something like this? Even though I love these things, even my eyes were glazing over. 

And then for some of the models that I didn't know as well, I just didn't feel like I could authentically convey how best to use those structures in a straight business format. 

So then I shifted, and it was going to be this weird analogy to the dinosaurs becoming extinct. It was going to be much more sci-fi oriented, like every part of the firm would be a comparison to dinosaurs on their way out. But that felt bleak and also just strange. 

And so in the end, I had a conversation with David Eckert, who has written his own book, and I couldn't figure out how to resolve these two things. I wanted to write a story, a business fable about this law firm, but I couldn't figure out how to make it realistic that any firm would take five days off, with all of its leadership off-site, to do something like this. 

So I was struggling, and I talked to David Eckert, and he said, “You need an inciting event to get everybody together, and it has to be so urgent that they would do this.” 

And so the inciting event that I came up with was that this midsize firm that has this really deep culture that it values and cares about deeply was about to be absorbed by a really big global firm and didn't want to be. But they also saw the writing on the wall with their financials and with the feedback they were getting from clients. 

And so the managing partner makes the decision with the chief innovation officer to pull everybody out of their work for a week and go through all of these different frameworks together, and educate them about the profession and legal education along the way. 

So it felt like somebody could read this and feel like, this is exactly what's happening at our firm. And I recognize these different characters, and this is a usable format to me. 

I also will shout out Sharon's colleague, Alexa Robertson. We did a workshop together with PLI using How Stella Saved the Farm, which was another business fable. And at the end, speaking of encouragement, Alexa came up to me and she said, “Have you ever thought about writing a book like this for the legal profession?” 

And I said, “No, I don't write books. It's not something I could do.” And she said, “I think it would be really good if you came up with a format like this for legal.” And then I remembered that conversation. 

Sharon Crane: It's funny. Did you get the dinosaur idea from How Stella Saved the Farm, which — I think I'm glad we landed on not that idea. Were you thinking about the animals in the book? How did that come about? That’s so interesting. 

Jen Leonard: No, I was just thinking of another era where something was disrupted massively. And it didn't make any sense. I mean, it really was. But the themes of the chapters — one was like “frozen in amber,” and it was legal education or whatever I picked for that chapter. 

And then, you know, birds are the only ones that survived. And so it was focused on why the birds survived and nobody else. It was just going into really weird places, so I scrapped that. 

But around the same time, Marielle and I were working on a proposal for a midsize firm for a multi-day retreat, and so we were sort of structuring this already. And it was funny because it was more time than we've ever had with a leadership team to do this. 

But we just kept saying, we're leaving so much on the editing room floor. It would be great to have a law firm for a week to do all of these different things. So it all came together at the same time. 

Sharon Crane: Well, I love — like I say, I'm biased since we published it — but I read it in two days. It's such a quick, easy read, and it's so fantastic. 

But what I think is so unique and useful about it is the different use cases. I can think of ten different people at law firms that can use this. 

So I'm curious. You do say in the beginning of the book that there are different ways you can use this book. You don't have to read it from cover to cover. But can you outline a little bit who the audience for this book is and how they can use it, other than just reading it as a straight business book? 

Jen Leonard: Yeah. The way I designed the book is that anybody who is trying to lead change in a law firm can use it as a guide and a resource, whether that's somebody who is at a departmental level and they're trying to guide their team through change in their function, or in a practice group, and they're working with lawyers who have specific personalities and trying to lead change. 

And they don't need a huge budget to be able to do that. They can use the exercises in the book to guide them through. 

But I think the biggest audience and the most impact is really if firm leaders are able to use this resource across their leadership team. And that is why so much of the book focuses on Julien, who is the managing partner, and Lucy, who's the chief innovation officer. Also, the names of my kids. So they're named after my kids. 

But so much of it is focused on what they're going through as leaders and how they structure opportunities for their colleagues to come together. They equip them with these frameworks, but they make very clear — Julien makes very clear in his opening keynote — that he doesn't have the answers to this. 

Change and transformation are not about one person knowing how to do everything. It's about that person setting the vision for their time together, and then creating environments where everybody gets to contribute to change. 

And so I think firm leaders are probably the best positioned to really use this to impact. 

Sharon Crane: And if I can just shout out that the other firm leader — and this was my previous role as an executive director — I think managing partners, people in the management committee, the chief innovation or knowledge officers, or the executive directors or COOs who really touch all parts of the organization, from associate development and retention to finances to innovation and pieces like that. 

I think it's really a useful book to do even over, like you suggest, a book club. Give it to everybody on the management team or the chiefs in a law firm and have everyone read it and talk about it over a series of lunches, or do a full retreat. So I think there are so many different uses for the book. 

Jen Leonard: Yeah. And you mentioned chief talent officers, too. I think on both sides of the employment relationship, people in law schools who want to empathize more with what's happening inside their employers and design programming that's either more collaborative directly with them or preparing their students to enter environments undergoing change. 

Sharon Crane: I will just say on the use case, too. I think with the way it's structured, it's helpful because if you are the chief talent officer and your real focus is on professional development, you can go to those parts. You don't have to read the book cover to cover. 

You can go to the part that's focused on your area, read that, and have the key takeaways. And in the back, you have a great appendix that gives the whole view of the retreat. 

But if you want to just duck in to get something that's specific to your area of focus, you can do that very easily without losing anything. 

Bridget McCormack: Yeah. No, I think that's one of the best parts about it as well. I’ve said this to both of you many times, but we present a lot to legal teams, law firms, in-house teams. And when people are struggling, sometimes a bite-sized, dip-your-toe-in-the-water approach is the best way to get started. 

And I feel like there are lots of ways to do that with this resource. I think it's going to have a tremendous impact. And I don't know of anything else like it on the market. So it's really such an important contribution. And thanks to PLI for publishing it, and to you, Jen, for writing it. 

Characters, Skeptics, and the Reality of Change 

Bridget McCormack: But the characters feel very real. I know they have your kids’ names, so I know they're actually fictional. But how much of them are drawn from people you've come in contact with in your consulting practice? Because, in fact, you do law firm retreats. 

Jen Leonard: Definitely inspired by all the many people I get to meet in our work. And a lot of the characters are composites of people that we meet in our travels. 

Some of the junior associate characters are inspired by students that I've worked with who are now junior and mid-level associates, and I hear from them what their perspective is like working inside of a law firm. 

But the one character that I loved the most was the Robert Kim character, who is old school. He's a senior partner. I think he's the oldest in the firm. He hasn't really had a chance to pick up his head during his career to really see what's happening around him, and he has this chance to understand how he can contribute to the junior generation in a mentorship role. 

And then there's the skeptic, who wants nothing to do with this because they're very successful in the world that exists today. And that is certainly understandable and common. 

I would say that most firms that do hire us to come in to work with them have leaders like Julien and Lucy, who understand that the world is changing, and they don't know exactly what to do about it. But they are true leaders and care deeply about their organizations. 

And then in the middle layer, you've got the partners who have recently become partners, are actively trying to build their books, are caretakers of parents and children, and expected to mentor down and also help the generation above them think about succession planning. 

And so those characters — I have a lot of empathy for them because they're struggling with so many different things and don't have a great way to contribute to transformation because they don't have the time and energy. 

So they were all fleshed out from all different groups that we've seen, and individuals, for sure. 

Sharon Crane: For most of the characters, I could see people who I've worked with before. 

But also, I'm one of those people who — I don't like sad endings, but I like realistic endings for movies, for example. You don't always get the girl. You don't always get to go off into the sunset. So I like realistic endings. 

And from the very beginning, there's somebody who's just like, “This is ridiculous. I'm out. I'm going to get through this, and then this is over. I'm done.” And that is definitely going to be a reaction of some who are very happy with the status quo. 

So I'm glad that you put that person in there. And also, without giving away too much, there's not an easy resolution, I would say. And that's also realistic for people to know that this is actually a continuous process. 

So I think it's realistic in that way. In addition to the portraits you paint, I think the whole exercise is realistic because there isn't a nice, easy way to wrap this up in a bow. 

Jen Leonard: I loved William. He was like the typical lawyer personality, I feel like. And I actually scrapped, Sharon — you would have liked it — I had a couple of scenes in the original draft where would go home to his wife, Margaret, and he would be complaining to her about all these exercises they made him do. And he’s away from his billable hours, and this is all nonsense. And she counsels him to just go through it, because these things never take hold. Nobody's really going to do these things. 

And so you see that — I don't want to spoil it — but at the end, that's sort of what he did in the second half of the book. He kind of stayed quiet, and then he encouraged the ideas because he was encouraged by his wife to think that they weren't going to happen. And then when they actually did, he was not pleased. 

But also to your point, innovation, change management, and transformation happen continuously and forever. I think sometimes when we meet with different people, it's like, “Let's bring somebody in for a month and do some workshops, and then we've checked our innovation box.” 

And I really wanted to make it clear that it is messy, and you're losing people along the way, and it doesn't feel good while you're in the process. And that's how it should be. 

Sharon Crane: I also thought it was interesting about the skeptical opinion or approach, because as I'm reading this, too, I'm thinking there are some people who just find workshops and development things like this — it's not their thing, and they dismiss it all. 

But what I think is important is, like with anything, you take the nuggets that make sense to you and work for you. Each of the chapters has a key takeaway. And even for the person who is a rainmaker and is currently benefiting from, let's say, the status quo or how things are, the questions about how you can better understand your client and how you can workshop with other partners or even your team to provide better client service — and you’ll have all these “how might we” statements and things like that — if you're a good rainmaker, you're probably doing that anyway. 

But I think it helps reinforce some of the things that you can take, even on an individual level, to help yourself or your enterprise. 

So I was reading some things, and I could see people rolling their eyes, like, “We would never do this.” But taking it away from the retreat and the actual workshops, again, I think there are key takeaways that, as an individual, you might say, “Actually, this would be useful for my department or my key client,” that people should try out. 

Jen Leonard: Yeah. And also, as you know, Sharon, when you're rising through a law firm, you're rewarded for certain valuable activities years one to five. And then almost overnight, the firm expects you to develop a totally different skill set to work toward partnership. 

And I think the design thinking methodology introduces that group to the concept of empathy. When you've been in a law firm, you are sort of siloed, and you have a law firm perspective of the relationship. 

And like you said, hopefully this offers people who are either in that role or ascending to it the chance to think outside. And that's why we had, in the book, the outside general counsel who come in, and they are interviewed about the things that frustrate them and delight them about their firms. 

Sharon Crane: And, you know, it's interesting because that does happen in law firms, for sure. 

And I would say you gave away a lot of secrets in this book because at the very end, there are basically a couple of literal ideas that law firms could consider if they're not already doing it, and implementation plans of how you could do it with tweaks. 

You look at your own space and you say, “I love this idea, and this won't work for that reason.” But you literally lay out almost a blueprint of how you could incorporate some of the ideas that meet the most challenging issues that we've mentioned — intergenerational conflict, AI, and all those types of things. 

So there's a real blueprint here. So thank you for sharing your secrets. 

Jen Leonard: Yeah. And I think the point of the blueprint is it's not uncomfortable to give away ideas and implementation plans because it takes the human beings actually executing them. 

Our podcast is all about AI, and AI can generate all sorts of plans for you and things you could do. But unless you have human buy-in and human engagement, none of it actually works in the end. And the implementation is the hardest part. 

AI as a Writing Partner 

Bridget McCormack: You actually have a note at the end of the book about using AI as a partner in writing the book. Can you talk a little bit about that and what that was like? 

Jen Leonard: Yeah. So that was one of the more interesting parts of this, because of course, any other time I would have thought about writing a book, these tools were not available to do it. 

So approaching something as enormous as a book project and knowing that I could amplify it and augment it and make it sharper was also confidence-building. 

But the way that I thought about using AI is the same way that we teach our law firm clients and others to use AI. I think when people think of people using AI for writing, they think of somebody just putting a prompt into ChatGPT and taking whatever they get out and editing it. And that's not at all how I worked with AI. 

I thought about the spectrum of human-machine collaboration and what things I really wanted to keep mine alone. And for me, that was the drafting part. I wanted to draft this book and then work on it and refine it. 

At the other end of the spectrum was research. Although actually, I have a great researcher, Genevieve Tung, who did early research for the book and also read early drafts and could tell you for sure that this was a human draft because they were early. And she provided amazing feedback. 

But I used Perplexity a lot. If I was working in the book and there were things like numbers, or I wanted to make sure that I was saying something factually accurate, I would quickly run a search in Perplexity, which of course gives you the underlying resources themselves, and take those and make sure that I did it as a sort of fact-checking or deepening of some of the things I was exploring. 

And then there's everything in between. Right? So it definitely gave me lots of feedback when I was drafting or editing, like, “This works well. This doesn't work well.” And across different parts of the book, “This doesn't map to this.” 

And then, of course, I had your exceptional team and Lori reviewing everything as well. 

There was one part in the book where I did use AI for its ideas, and I thought a lot about that. And the reason I decided to do it is because it was in the ideation section, Sharon, where they were coming up with all new ideas. 

And the whole point of ideation activity is you have lots of different people coming up with lots of different ideas. And I felt that if I were the only one to put my ideas in the book, it wouldn't help the reader see the point of divergent thinking and voluminous thinking. So I did work with AI to come up with different ideas that I used in the book to show that part of it. 

But it was a really interesting experience, and I know I have writer friends who feel very strongly about not using AI at all in writing. But my goal was really to inform the reader and equip them with the best possible knowledge and frameworks that I could. And that's how I thought about it: centering the reader. 

If I were going to submit something for the Booker Prize or something like that, I would take a totally different approach, I think. But I'm not doing that. 

I don't know what you guys think about that. I feel like it's an emerging area of collaboration. 

Bridget McCormack: I mean, I use it as a co-intelligence all the time, not only for ideas, but for more. I have a lot of ongoing projects that are set up in Claude as artifacts, and I'm working on them in an ongoing way. And I can't imagine not having it as a co-intelligence. 

I haven't given the latest — what is it, 4.8 that came out last week — model, I haven't really kicked the tires of it yet. But I hear a lot of people say it's a little bit better at pushing back on your ideas, which is a good thing. 

I want more of that. I don't want to be told all of my ideas are brilliant, because I know they're not all brilliant. That's the point. I have lots of them. I want you to help me think through which ones actually have legs. 

But it's hard to imagine, from now on, not using it as a co-intelligence. And I thought the way you talked about it is a great roadmap, actually, for folks who are just starting to think about how to incorporate it into a lot of the things they do. 

Legal History, the Billable Hour, and the Future of Lawyer Training 

Bridget McCormack: Just about every profession is trying to figure out how to make this transition we're all making with how to fit this co-intelligence into what we do. 

And we all have our own constraints. The constraints in the legal profession have some historical precedent. And you have a history lesson in the book as well, which it seemed to me was kind of important for lawyers who are focused on how change management is going to work within our profession. 

You trace it back to the Cravath system and the billable hour. Can you say a little bit more about that and why you think it's important for lawyers to know that history, which many don't? Why does it matter? 

Jen Leonard: Yeah. And before I jump into that question, one more thing I wanted to add about the AI collaboration, the co-intelligence collaboration. 

Another thing that I did, which we teach our clients how to do, is used it to reverse interview, and so it helped me stimulate my own thinking about the contents of the book. And as you both know, I think right now it works best for subject matter experts. 

So where it would give me ideas where I knew, you know, a law firm environment would never support that, I was working alongside it, but in control of it the whole time. And I love reverse interviewing for stimulating thought. 

But to get back to the question about the history lesson, I think it's important because I, like many other lawyers, have never known another private sector legal model. 

So when I started in a law firm, I just accepted it almost as biblical that this is how these places run, and they're designed perfectly well, and who am I to question anything? 

And the more time I spent, especially when I was at Penn, learning more about the history of the legal profession, I realized that the system, which emerged in the early 20th century, was a really great example of well-designed businesses. It really met the moment. 

It allowed people to develop — well, men to develop — at the right pace for them in ways that cultivated relationships with their clients. And that world is really gone for lots of reasons. 

And then the rise of the billable hour was really not to benefit the firms. It was actually the outcome of a consumer lawsuit against law firms for the lack of clarity in the way that they would bill their services. And it unintentionally gave rise to this system that slowly moved lawyers away from people and toward corporate clients. 

But it was an effort after that ruling to give more transparency around what they were actually doing. And so the point is that none of this is how it has to be. And in fact, in a lot of cases, it's not, in my opinion, how it should be in a modern business. 

But I think it's important to just highlight that for people who might not know the history. And then I mention in the book that the billable hour’s high watermark, in terms of numbers of hours across the Am Law 200, was really back in 2003, and it's been steadily declining ever since. 

We're blind to that because the rates have gone up so much that it's remained a healthy business model. But to me, it shows how much under the surface has already changed and will be accelerated by AI and other forces. 

Sharon Crane: I think the history is so important because it shows that, as you said, it met the moment at the time. 

So there has been innovation in legal services. That's how we got some of these things that we have now. So it is possible to do it. We just haven't done it on a large scale in a while. 

So I think it's important to remind people that things have evolved because they were trying to be more transparent and trying to be more helpful to clients. And now what clients want is something different. 

One of the other things that you mentioned — and you mentioned earlier on as we were talking about law schools and how they can use it — is the model of training, from theory in law school to practice under the Cravath model, with apprenticeship and clients subsidizing that training by paying for first and second years. 

That has long been of concern, because if you come out of law school, you don't feel particularly prepared. And the apprenticeship model, as leverage has gotten to be very important, has kind of fallen away from what it used to be: one-on-one partners and an associate learning from that person. 

So where do you think training goes now? Where should that be? 

And as a legal education organization focusing on preparing lawyers for the future and for their current practice, it's really important for us to provide programming that's helpful and also partner with law schools and law firms to make sure people are ready. 

But how do you see that changing, or what do you think would be useful in that regard to get current lawyers prepared for what's to come? 

Jen Leonard: Well, it's one of the reasons I love working with you and your colleagues, Sharon, because I think PLI has such an important role to play. 

There is such a gap, especially in the handoff between schools and employers, and especially because of the confusion that AI has created across those groups, that we really need new models — and models that are capable of being flexible. 

I was talking to a firm leader last week who was grappling with this idea, and we were talking about how the law schools just are not fast enough to keep pace. 

And I said, for the next couple of years, it may be the case that you almost have to build an internal version of a law school to upskill your new associates sufficiently so that they're contributing value in the way that you expect them to. And that's not anything that any law firm, A, is set up to do, nor is financially incentivized to do.  

So I think, to the earlier point of partnerships and collaborations that are unusual and unorthodox, this is the moment for that. Because that handoff point, in my opinion, has been messy for a long time. And now it is — not to overuse this word — but about to be disrupted, I think, in many ways, in terms of what they need and what they actually are equipped with going in. 

Sharon Crane: And that's why it's fun to do the experiments — to see exactly all of us collaborating with different groups, whether it's consultants or law schools or pretty innovative law firms, to figure out how we all help. 

Because it's going to benefit all of us if we have lawyers who are ready to meet the new moment with AI in training. And it's super tricky. 

I think we're going to see, obviously, more, and we're looking to do some more experimental and experiential and simulated learning so that people can do more practice. 

Everyone's concerned about the current work being given to AI, as it probably should be. But then, as everyone's talked about, how do you gain the skills and the judgment to really supervise the output? 

So that's something I think we're still going to have to wrestle with a little bit. And I think, to your point, it's probably a partnership across all of the areas that we talked about. It's law schools and consultants and organizations like ours and the AAA and law firms and in-house counsel, to be honest. 

Bridget and I talk about this a lot: what needs to happen in the future to upskill teams and get them ready. 

And I don't know, Bridget, if you have other thoughts to add. 

Bridget McCormack: Yeah. I mean, I'm ultimately pretty optimistic. 

I think the answer is coming from two different places. One is, I'm not sure that doing grunt work really was what created great judgment to begin with. I think we're flattering ourselves if we think that that training program was excellent. 

Sometimes individual new lawyers got excellent training because they had an individual partner who really took an interest in them, and others had significantly less excellent experiences. It was not excellent across the board. 

So I think the opportunity to rethink how we do that is a great one for the profession, because it's going to let us step back and create something significantly better. 

There's also going to be all kinds of new legal needs. Jen knows I'm an optimist kind of across the board. I think lawyers are going to have more to do, and the opportunity to figure out how we build senior lawyers in the profession with new ways of training them feels like good news to me. 

There are lots of other professions where they don't train people by just having them do the work that people at the top of the profession think is boring. 

Astronauts — they don't send them to clean the rocket ship, or even just go do a training mission and see how it goes. Like, go see what's out there in space and tell us. 

But I do think that the one place — and this might be a good final question for you, Jen — builds on Sharon’s flag, which is an important flag. 

I don't think we've worked it out yet. Just because I'm optimistic that we will work it out and it will make it better isn't a good answer to what it is going to look like necessarily. 

And the folks that I want to have the best answer for are the new lawyers, right? The lawyers just coming out of law school. 

In your book, the junior associate, who is quite self-aware, is worried about how she's not going to learn what she feels like she wants to learn if she can outsource her thinking to AI. And that's the shortcut that the pressure of the business is going to require her to take. 

It's really going to get in the way of her becoming the seasoned senior lawyer that her clients need. Do you feel like you have good news for that group in particular about where we are or where we're headed, at least maybe after we get through the messy middle? 

Good News for Junior Lawyers and Closing 

Jen Leonard: I really do. I think we're going to retain a lot more lawyers in the profession. 

I know I left because I didn't want to sit and sift through bankers’ boxes and mark relevant and not relevant. I didn't really understand why I was doing that with my intelligence, and I wanted to do something different. 

So I think if they are able to engage in some simulated education that helps them get up to speed more quickly, I am very optimistic about that, actually. 

And I had two junior associate characters: Priya, who is the self-aware one who's worried about the loss of her critical thinking skills, and Alex, who is all speed ahead with technology. And it reflects the associate groups that we see in our work. 

They are very much at the ends of different spectrums, and I don't see a whole lot of gray area there. So I wanted to show how the two of them and their personalities, if they learn from one another — and they had table conversations in the book together — can meet in the middle. 

One can moderate the one who is just like, “Let's let it all loose.” And the other one could learn from the one who is worried about these things as they grapple with it together. 

But overall, I'm very optimistic that if we do this right, the life of a junior lawyer will be much better than it has been in the past. 

And I want to thank you both. I know we're at time. It was so generous of you to give me this time to talk about the project. 

And Sharon, it’s so amazing, your team, all the work that they do to bring different authors’ ideas to life. And I'm privileged to be counted as one. 

Sharon Crane: Oh, thank you. I mean, we love working with both of you. 

And again, thank you for having me on. I will go back to being a listener and let the professionals — you two — be podcast hosts. So I appreciate it. Thank you so much.