Summary
In this episode of 2030 Vision: AI and the Future of Law, Bridget McCormack and Jen Leonard explore how artificial intelligence is reshaping the legal job market and what law firms must do to stay competitive. They dive into the World Economic Forum’s Jobs Report 2025 and the Thomson Reuters & Georgetown Report on the State of the Legal Market, breaking down the key findings and their implications for legal professionals.
From the rise of AI-powered legal roles to the leadership challenges law firms face, the hosts discuss the critical skills lawyers will need, the importance of AI strategies at the C-suite level, and how firms can prepare for the coming transformation. With law firms experiencing record profits yet facing mounting pressure to innovate, this episode highlights why 2025 is a pivotal year for the profession.
Key Takeaways
- AI Aha! Moment: How AI is Transforming Legal Research: The hosts share their AI insights for the week, including how generative AI is being used for legal research, document analysis, and strategic decision-making.
- Defining Persona Prompting & AAA’s AI Innovation Initiative: The hosts explore the concept of persona prompting—how lawyers can use AI to simulate different perspectives, enhance client interactions, and refine legal strategies. They also introduce the American Arbitration Association’s new AI initiative, which focuses on helping legal organizations navigate generative AI, implement change management strategies, and upskill their teams for the future.
- AI and the Future of Legal Jobs: The World Economic Forum’s Jobs Report predicts major shifts in employment, with legal roles evolving due to AI automation and the demand for new skill sets.
- Law Firm Strategy in 2025: The Thomson Reuters & Georgetown Report highlights that while law firms had a strong financial year, only half have begun integrating AI strategy at the leadership level—creating a growing divide in the market.
- Upskilling and Adaptation: With nearly 40% of workers’ core skills expected to change by 2030, legal professionals must embrace analytical thinking, emotional intelligence, and AI literacy to remain competitive.
- The Innovator’s Dilemma in Law: Law firms face the challenge of balancing immediate financial success with long-term strategic innovation—risking stagnation if they fail to invest in AI-driven transformation.
- AI as a Competitive Advantage: Forward-thinking firms are leveraging AI to enhance client services, streamline legal research, and improve operational efficiency—while those lagging behind may struggle to attract top talent.
- Leadership in the AI Era: Effective law firm leaders will need curiosity, courage, and humility to guide their firms through the rapid changes ahead. Successful firms will foster collaboration across legal, tech, and business professionals to shape the future of legal services.
- The Global AI Push: Governments and corporations are investing billions into AI education and infrastructure, signaling a major shift that will impact all industries—including law.
Transcript
Jen Leonard: Hello everyone, and welcome to the newest episode. I'm your co-host, Jen Leonard, founder of Creative Lawyers—here in three dimensions with the amazing Bridget McCormack, President and CEO of the American Arbitration Association. Bridget, we're in person!
Bridget McCormack: It's so exciting to do this in person for the very first time and to be in Philadelphia, which I adore.
Jen Leonard: And we also had a chance to meet our wonderful producer, Aaron Tran, who's here in person. He’s the best.
So today, we're really excited because a few reports have come out recently—reports on the state of the jobs landscape generally, and then an interesting report about legal in particular. And because both of us are really, really interested in how AI will impact jobs and the future of the legal profession, we thought this would be a great episode to host in person.
Jen Leonard: And as always, we continue our format of starting with our AI Aha! – the things that we have used AI for that are magical since our last recording – then sharing a definition in this interesting new world of AI (something that people might want to familiarize themselves with), and then we'll jump into the main topic today, which is covering the World Economic Forum’s jobs report for 2025 and the Thomson Reuters/Georgetown Center for Ethics in the Legal Profession report on the state of the legal market for 2025.
AI Aha! Moments: How AI is Transforming Legal Research
Jen Leonard: So, Bridget, I'll turn it to you to kick us off with the AI Ahas. You always have really interesting ways that you're using AI. Can you share something you've used it for?
Bridget McCormack: One of the reasons I'm here in Philadelphia this week is the American Law Institute Council meeting, which is the governing board of the ALI. It meets here in Philadelphia on Thursday and Friday, and I was elected to the Council last May. I've been a member of the ALI since 2012. The ALI, of course, is the organization that tries to bring some clarity and transparency to different legal areas. They issue these Restatements of Law, which courts, scholars, and lawyers rely on to understand what the legal principles are in a particular area. Apparently, at the Council meeting we will be discussing many drafts of restatements. And I get to give a little intro speech to the Council as to who I am and why I'm here—which is a good question, honestly.
I decided to brainstorm a little bit with my friends—well, actually a couple of my friends. I did it with Claude and with ChatGPT—about the history of the ALI and what the founding members of the ALI were concerned about. It feels to me that right now my main familiarity is with the Restatements. And when I was a judge, I did rely on them quite a bit; they're very helpful resources to understand, especially a new area of law where you don't have any background. But they're very dense, and they get denser every year, right? Because there are so many different common law jurisdictions that take the law in different directions.
The ALI does a really nice job keeping track of all that, but it's no longer, in my view—I don't know if it ever was—a resource that anyone other than smart lawyers and judges can get a lot out of. It seems to me that there might be some opportunities with generative AI tools to think about ways the ALI could update some of its services and offerings, consistent with its founding mission, by using generative AI.
You would not be surprised to know that Claude and ChatGPT had lots of great ideas, and they think it's a very exciting project to think about the ways that the ALI might use generative AI with its resources to bring even more clarity, transparency, and information about legal rights and responsibilities to people who are not lawyers. So I have a bunch of those ideas. I'm going to try them out and see how they go; I'll let you know.
Jen Leonard: Yeah! That's so cool. Do you have any one of those ideas that you'd be willing to share?
Bridget McCormack: There are a couple of ways in which, if the ALI wanted to, the technology could clearly be used to simplify what the Restatements now do—in plain language, in any language. So you could imagine producing resources that were basically Restatements for non-lawyers that would be very simple, and the chatbots have lots of creative names for these.
If the goal was to make sure you're bringing clarity and transparency to what the rule of law is—what it requires of you, what it provides for you—it's a great technology for doing that. I guess I'll have to learn a little bit about the funding model and how much they count on their Restatements for income, but still... I mean, when it (the ALI) was founded here at the University of Pennsylvania, foundations funded the project, and the founders were like, "We have law just going all over the place out there in all these states, and we really need to bring some clarity.”
And it was a pro bono effort, really. It wasn't like a money-making effort, and it's still a nonprofit. So I don't mean to be hung up on the funding model, but obviously we'd have to figure that out.
Jen Leonard: That period about 100 years ago is so fascinating. I know that the AAA emerged 100 years ago, the ALI, the Practicing Law Institute—it was this whole era of such complexity and also such entrepreneurial spirit among lawyers…
Bridget McCormack: And collaboration. The ALI was actually a collaboration between academics, judges, and practicing lawyers. It was the first time there was that kind of overlapping stakeholder collaboration around something where everybody was like, "We have to do something about this. We can't just have different rules of law growing up all around the country. We need to bring some clarity and have some understanding of what the basics are." And so that collaborative piece is a good model for what's possible right now.
Jen Leonard: I was just going to say, I feel like you work on a lot of different projects around leveraging AI. I'm involved in some projects too. Do you envision that this era of the profession will have some sort of lasting collaborative efforts emerge?
Bridget McCormack: I feel like it certainly could, and it's my hope that it will. You hear me talk about stakeholder silos and how they really don't serve us, and I think they have disserved us in solving a lot of our big problems in the profession. And I think they will really disserve us if we want to figure out how to make sure that AI transforms the legal profession for the better—and the practice of law for the better—not just for lawyers, but for the people we serve. And I don't think we're going to get there without breaking down those silos. I have big hopes that maybe, on this 100-year anniversary of all that collaborative innovation, we can do it again. Now's the time.
Jen Leonard: That's very cool. And the other group that emerged during that same period (that we'll talk about today) are law firms. Their modern form developed in response to all of this complexity as well, and they’re serving their clients in really interesting and dynamic ways right now too. It's very interesting—it's like an echo through time, 100 years later. Yeah. That's a very cool use case.
Bridget McCormack: It's another one of those creative partner scenarios. We got into some deep rabbit holes—I was like, "Wait a minute, why wouldn't the ALI be exactly the right leader to...?" It was fun. I like the thought-partner aspect of these tools.
Jen Leonard: That's very cool. Mine's so boring in comparison! And (as we talked about before hitting record) I'm going to work on saving my most creative use cases because I forget about them by the time we get here. But since I was cramming and trying to prepare for today, I ended up using the same use case that I'm using for today's episode, which was Google's DeepResearch tool (which I love) to prep for this conversation. The World Economic Forum report in particular was lengthy, and we really wanted to do a high-level summary.
So I asked Google’s Gemini Deep Research to surface the report and any surrounding editorials about it—particularly any weaknesses in the report that I was interested in—and it did the whole thing where it generated its research plan. Then I made some edits to it. I think it's just a very cool use case for anybody.
Bridget McCormack: It's incredible. I mean, I've used that tool a few times a week for the last couple of weeks. It's really a great tool.
Definitions: Persona Prompting & AAA’s Vision for the Future
Bridget McCormack: I thought I could ask you the definition question. Persona prompting. What is persona prompting? What do we mean by that?
Jen Leonard: So, persona prompting—and I know you have done this in very interesting ways, including (this is a slightly deeper version of persona prompting) when you actually created a custom GPT of Frances Kellor, the founder of the AAA, and engaged in conversation with her. But persona prompting, as I understand it, really refers to asking the AI to adopt a persona and then interacting with the persona that you've asked it to adopt. So it's really helpful in getting different perspectives.
I think it's helpful for lawyers in preparing for things like oral argument. I did a workshop with a group of lawyers where they were analyzing a hypothetical RFP from a corporate client and had them do persona prompting and say, "I'm a GC of a higher-ed institution. Here's what's in the four corners of the document. But what are things that I might not have put in here that a modern-day GC of a big university would be thinking about?"
And that led the lawyers to think more deeply about different services they could offer that go beyond the scope of the RFP, but really show how empathetic and intuitive they can be in understanding the client.
I love persona prompting—I use it all the time and definitely encourage others to use it. But the reason I picked this definition this week is because I was with you and many of your team last week filming a project that you and your team have built together. And your colleague Jason Cabrera, who's your AI Enablement Professional, was talking about persona prompting during the project. So I also thought today's topic lends itself nicely to sharing a little bit about that project. So, if you would be open to sharing what you're building…
Legal Course Teaser
Bridget McCormack: We're pretty excited about it. We've been diving into how generative AI is going to affect our core business as well as our operations for almost two years now. And I've said many times: I'm lucky that I inherited a team and a program that already had a structured innovation program. So we had a great place to build out some of what that change management looked like, even though nobody really knew what it was gonna mean for all of us when we started.
We just started a number of different work streams and processes, then put some governance around it and built out what, in retrospect, looks like a pretty great way to approach change management for a legacy legal organization trying to figure out what generative AI is gonna mean for your business. And we think it's now pretty useful for other legal organizations—law firms in particular, but probably also in-house departments, in-house teams, and even law schools. I've been asked to talk to enough law firms (often with you) and in-house legal teams about what we're doing. And many of them have said, "Can you put that together in a course and come teach us how you did it?"
And finally, after enough of them said that, I was like, "Well, maybe we can." We have a line of education products and services, and we do education around alternative dispute resolution. Why not around this particular kind of change management for legal organizations approaching generative AI and what that means for their business? And I'm excited about it. Jason is featured, but so are a lot of my other team members, all of whom have been great sports along for a really interesting ride. We're pretty proud of what we've built and excited to talk about it. We're gonna announce it during Legal Week in New York at the end of March, so I'm very excited to talk more about it as we release it.
Jen Leonard: You should be so proud and so excited. You were so early to jump on this. And as you said, you have an incredible team and an incredible structure that lent itself to really moving quickly. Now that you're two years in—and we'll talk today about law firms and their challenges for 2025, and just to spoil it a little bit: only about half of firms have started to elevate their gen AI strategy to the C-suite or leadership level—I know that a lot of people out there in our industry will be looking for guidance like the guidance your team has created.
Main Topic: The 2025 Legal Jobs Report: Key Findings
Jen Leonard: So maybe we can jump in and talk generally about the challenge around upskilling, the challenges ahead in the jobs market, the opportunities. And helpfully, the World Economic Forum recently created a really detailed report about what it sees as the future of the jobs market. So, Bridget, would you be open to walking us through a couple of the key findings?
Bridget McCormack: Absolutely. I'm excited to talk about this report. In some ways, I don't think it's surprising—and probably won't be surprising for most of our listeners. In fact, maybe they've already heard about it or seen it in their social media feeds. But the World Economic Forum report drew on the perspectives of over a thousand leading global employers that represent more than 14 million workers across 55 economies and 22 industry clusters.
A very large group of employers contributed to the findings and the trends. And the trends are what you might expect if you've been following the news or reading anything in the last couple of years. The rapid advancements in AI and technology in general are transforming industries at a pace that nobody really saw coming, and it's creating both lots of new jobs and displacing others. Interestingly, they forecast more jobs being created than displaced.
Which doesn't mean there aren't significant change-management issues for those of us who want to make sure that we can upskill or reskill (or co-skill) our awesome staffs. There is a lot of work ahead, but I think it makes it more exciting and it underscores something that I think you say a lot in presentations: that the only bad thing to do right now is nothing. If you're a leader of an organization, this change... it's a cacophony at this point and you can't ignore it. And so the only mistake you can make is to just think you can keep ignoring it. And I think that this report, because of its breadth and depth, makes that really clear.
I will say that our friend on the Marketing AI podcast, Paul Roetzer, made a really good point: the people responding to this survey (or however they gathered the information) probably don't even fully understand how quickly things are changing. They're likely not super-users of the technology or super followers of the leaders in the space—you know, they're not trying to interpret Sam Altman's 3 a.m. tweets.
So if anything, the responses might not be urgent enough or might not fully appreciate how quickly things are changing. But with that in mind, some of it I think is not surprising. The report predicts an increase of 78 million jobs globally by 2030, with 170 million new roles created and 92 million roles displaced. That, to me, seems like good news. I know it's scary news with all the change management, but overall it's good news. There is a lot of work to do and there's gonna need to be a lot of education to get people ready for those new jobs.
The roles that companies are going to need include AI specialists, machine learning specialists, data specialists, engineers, and business intelligence analysts. These might not be traditional jobs that many people have trained for, but they're trainable jobs. And the kinds of jobs that are probably going to go away are clerical roles in all different kinds of industries, including legal. In this report they listed "legal officers" as one of the jobs on the chopping block. I'm not sure what that means, but it sounds like judges—or maybe lawyers. I don't know. Lawyers are officers of the court...Judges are kind of officers of the law…I don't know. It sounds like legal jobs are potentially impacted, and I think that's of course right—they're clearly going to be impacted. But I think, like the rest of the industries, there will be more work created; there's going to be plenty of work to do. It's the getting from here to there—which is what we've been talking about for many months now and will have to keep talking about—that's the challenge. But I think everybody else should be talking about it at this point as well.
One of the other interesting things about the report (and this is something I love listening to you present on) is the kinds of skills that are going to matter for the future. If you're thinking about what your workers' core skills need to be by 2030—because you want to figure out how to upskill or reskill or co-skill—what are the skills that you want to be training people to do? What are the human skills that are going to matter in the coming years?
And again, I don't think this is happening tomorrow. I mean, I've said this before: it took people 10 years to get on the elevator after it was built. But, you know, the elevator makers didn't go away in those 10 years. They hung in there. And they're doing okay now. So, what are the human skills that people should be thinking about?
Jen Leonard: Yeah, and you mentioned how long the lag time can be between a technology emerging and the adoption of that technology. But in the report it says that just under 40% of workers' core skills are expected to change by 2030. So we're at 2025 now... I mean, that's nearly half of the skills that workers bring to the table in the next five years. It seems like such an enormous change.
And like you, I'm really excited about all the opportunities it creates—particularly to do things that are much more interesting and creative than things we've done in the past. But I also think that it requires real leadership at the educational level and at the organizational level. And I think it's too easy right now to put your head in the sand and still be maybe not skeptical—like, maybe deep down you believe it—but just not sure what to do or not interested in doing it.
And so, I'm also going to echo Paul Roetzer, who (for the first time, I think, in his last podcast episode) said that he recognizes how hard it is to change jobs, but if you're working in an organization that has no AI strategy, you should really consider moving to a company that does. And I think for the second part of our conversation today—focused on law firms—one of the biggest things on the horizon is a bifurcated landscape where some firms are addressing AI and actively talking about it versus the other half that aren't (at least not yet).
If I'm someone graduating from law school, I can see all around me what the future is. I'm not going to be interested in going to a firm that has no AI strategy in place. So in addition to the AI strategy and all the tech skills that will be required in understanding data and privacy and cloud computing and all of those things, I think the really exciting thing—and the thing I know we both share an affinity for—is humans and the skills that they bring to the table.
The report really highlights that these skills will continue to be important: analytical thinking and innovation, complex problem solving, creativity, originality, and initiative, active learning and learning strategies (which I also love). I just think metacognition and understanding how to become a lifelong learner are things we're relatively late to, as a profession, in terms of our skill set.
Not necessarily in terms of understanding the law—we constantly follow legal developments—but in terms of our business models and the way we bring ourselves to our work. And the social-emotional skills will be even more important, like leadership and social influence. (We'll talk a little bit about this later, when we discuss what we see in leadership in law firms and legal organizations.) I love resilience and stress tolerance and flexibility. And I'll again cite Larry Richard's research about lawyers' low sociability and low resilience and low tolerance for change, and how much of a challenge that will be—and the need for emotional intelligence.
So I think the exciting news is that those attributes become even more important if we can leverage skills that allow us to understand how technology augments—and I know you talk about this all the time—how it augments and does not replace human beings.
Bridget McCormack: It's gonna be an interesting period. I think there are actually a lot of lawyers who have these skills or have them but maybe didn't get to build that muscle as much during law school or even after, and it should be exciting. I know a lot of these people—I know them in law firms; you know, they're my friends—and I think this is their moment. It's gonna be a fun transition, I promise.
Jen Leonard: Totally, totally. And all those innovators who have felt sort of constrained—shut down, asked to move toward the exit—because, to be fair to firms and other organizations, there really was not an imperative to be innovative, and innovation could have been a risk to your firm. And I think we're now entering an era where it's a risk not to be innovative. And I think that's very cool.
Main Topic: Thomson Reuters & Georgetown Report: The State of Law Firms in 2025
Jen Leonard: So maybe we can dive into the 2025 Thomson Reuters and Georgetown Center on Ethics in the Legal Profession report on the state of the legal market. I will just start by noting that this is Jim Jones’s final report. He sadly passed unexpectedly in December, and he was such a wonderful leader in the profession and chair of the Pro Bono Institute. I looked forward to reading this report every year when I first started teaching the Legal Profession.
Bridget McCormack: It was a resource that you relied on.
Jen Leonard: Yeah. And you know my co-teacher for that class very well, Mariel Stashefsky (who will be cringing that I said her name out loud). She and I co-taught Law Firm Business Models, and I was brand new. She sent me the Georgetown State of the Legal Market report, and we invited Jim Jones to come to our class. I really did not know who he was, because I was not from this world. And I remember Mariel introducing him to the students and going over his very impressive background.
And he was so humble and understated, and she would say, "You guys, this is a really big deal that Jim Jones is here." And she was so right. Every year, he would build the whole presentation from scratch for us, would stay after and answer every student's question, and was just a wonderful writer.
So we're very sad at his passing, but it was really interesting to read this report—which, as you said about the World Economic Forum report, is probably not unexpected in its predictions (its main prediction being that technology will come to define the legal market over the next five to ten years). But what's interesting to me about the report is some of its findings around what 2024 looked like for law firms. And, long story short, it looked very, very rosy for law firms across almost every practice area. Higher billing rates and higher realization rates (which is not always the case), and practices that included transactional practices that dominated the 2010s, but also success in countercyclical practices like litigation, bankruptcy, and labor and employment.
And you frequently see those as a seesaw, right? But they're all active and successful at the moment. I think changing geopolitics means that they will become even more active on both fronts. Just following how the banks did in Q4 of 2024, and all of what seems to be pent-up energy around M&A, I think the kinds of things that businesses need law firms to do, and people need law firms to do, are only going up and to the right. I think that's also going to be true for disputes.
I mean, we keep meaning to get to this episode where we're going to talk about the ways in which the barriers to filing lawsuits or filing demands for arbitration are falling away given technology. So I think the kinds of things people need lawyers for are just going to keep growing. I mean, the animal spirits are back in the market and lawyers are going to be off to the races.
It's how they do what they do that probably has to change in the meantime. I think it's a tough scenario for any law firm leader (or legal organization leader) who is grappling with the innovator's dilemma, right? Because the work is just everywhere, and what you've done historically has always worked. And it'll probably work this year; it'll probably work fine in 2025, maybe 2026. I don't know if it's going to work in 2028 if, you know, legal tech has grown to a point where new models now work, right?
Jen Leonard: No, I totally agree. And speaking of the innovator's dilemma—and being structured around what made you innovative in the first place—to our earlier point, these firms emerged 100 years ago, and the leveraged labor model they created to respond to all of that complexity was their innovation. And then, in the intervening decades, the billable hour emerged as the primary way of charging for services.
And they're structured as partnerships, which is super rare in a world where organizations are no longer a dozen partners who've known one another their entire lives and can have handshake deals. Now you have thousands of people—many of whom you'll never meet—in other countries all around the globe, and you're essentially acting as solo practices under the shared brand of your firm.
But the other challenge that that creates is that it's a short-sighted model for how you distribute profits, because everybody looks to profits per equity partner at the end of the year. And it's very hard for leaders to convince their partners that they should take some of the bounty they've accumulated over the past year and invest it in an unknown future—especially because there's so much lateral movement now.
And if you do that, and you take... (I don't even know how much money some of these people make, so I'm not even going to try to guess because it'll make me sad.) ...a lot. So if you're going to convince an equity partner to take some of their haul and invest it in the future, I can understand why that partner would say, "You know what? This is the same as practicing with another firm that's not asking me to give up part of my distribution to do this."
Bridget McCormack: Especially since they have sort of limited time. Most law firms give you an incentive to move out when you're 65 at the latest—that's how the model works. And so you're probably earning your peak partnership share around then. So the incentives don't always align with solving the innovator's dilemma. It's really complicated, I think.
Jen Leonard: If you had a design challenge to work against solving the innovator's dilemma, a law firm would be exactly what you would construct. You hear this all the time—at any reception after a presentation at a law firm, the most senior partners will say, "I'm so happy that I'm not going to be part of this and have to worry." My in-laws, many of whom work in law firms, say this to me all the time, because I corner them at family events and talk about this and terrify them.
Bridget McCormack: And they mostly try to run away from you now? Because it's all you talk about? (laughs) I know the feeling.
Jen Leonard: And so, the leadership challenge here is huge. And then you have these mid-sized firms, many of which are merging. One of the other trends in the report is the reliance so many GCs have on returning to firms they are used to, but also their increasing need for global footprints and global expertise. So you have smaller firms that have a cultural advantage in figuring this out, but the economics mean they're forced to merge with a totally different group—and all those integration challenges that go with it. So that's a challenge.
And another thing I thought was interesting in the report is how COVID sort of shook up a longstanding budgetary framework that law firms use, much of which was allocated to traveling to see clients, to wining and dining.
I know on-campus interviews are no longer in person—they're all over Zoom now—and that was an expense. During COVID, spending started to shift away from those three-dimensional human investments and into technology. And tech investment has increasingly outpaced inflation in law firms. So the report says that trend will continue and that there'll be a new need for investment in strategic leadership of gen AI strategies and in upskilling the people at your law firm. A lot to think about—none of which is really surprising, I think, but all of which is not easy to solve for.
Bridget McCormack: Leaders who get excited by these kinds of challenges should be waking up excited with their brains exploding every single day—especially given the position they're in, with how well they've done the last year or two, and then all of the incoming work.
They have the resources right now, if they want to, to really build a team to figure out this transformation, right? You know me—I'm a believer in actually building a separate team to lead a transformation. Nothing kills innovation like success, right? If you do one thing really successfully, it's really hard to figure out why you would not do that same thing tomorrow.
They're in a great position to do it. And so I hope there are enough leaders out there in the legal profession who wake up excited every day thinking about what this will look like. Because I do think we come out of it with a much better profession—a profession that people will really love going into and staying in for their whole careers, and telling their kids to go into. I mean, I think there's good news ahead if we manage it.
Jen Leonard: Yeah, I think if you're a law firm leader, you couldn't ask to be in a better position during this moment, to have just come off of a hugely successful year where, according to the report, every practice area you have is doing well and your partners should be pretty happy with their results. And you have indicators in our industry that I think other industries don't have—things like the size of your summer associate class and those of peer firms, as harbingers of things to come.
We’ve talked about this in presentations: we will be somewhat slower in adapting than other industries, for lots of good reasons. But you have the total opportunity, like you said, to define a vision for what you want the future of your firm to be, to leverage those powers of persuasion that you have as a top-notch lawyer, and to chart a vision and ask people to come with you. What other attributes do you think a leader needs to have? And conversely, which types of leaders from the past who were very successful at the top of these organizations do you think might be on their way out or not as sought after?
Bridget McCormack: Yeah, you know, I think some of the skills that leaders need right now to manage the change that's ahead are things like curiosity and courage. I mean, I can't tell you how many times you will say to talented senior people that you work with that we're doing this crazy thing—we're going to figure out how this new technology is going to transform our business—and people will look at you like you're nuts. And so you have to have some courage in your convictions.
I think emotional intelligence and the ability to manage people in new roles. How can you see how your team might look in the organization of your future? And those are not necessarily the kinds of skills that maybe leaders of legal organizations were recruited for historically, but I think they're going to be critical. There’s probably others…
Jen Leonard: The only one that I would add—and it's really hard for lawyers (and they make it harder than it needs to be)—is humility. I think law firm partners are accustomed to being the subject matter experts, and they're sought after because they know everything about a given area. For many, I think this is uncomfortable because there's no clear answer as to what happens next.
I think that's liberating. Being able to say, “I don’t know what happens next, but I know that what happens next is going to be different than what happened before.” And here are the things that we can do as a community to learn together…
Bridget McCormack: So that we're ready for when it happens. Like, we're prepared.
Jen Leonard: Exactly. And I think that should be a relatively easy case for a talented leader of a law firm to make. But it does seem to be something that’s uncomfortable. And also, reaching out to clients and saying—I think this window is rapidly shutting—but saying, “We don’t know exactly what’s going to happen, but we believe the future will be different and we want to co-design it with you.”
We’ve talked about this in other contexts, but I think right now there are opportunities for these firms that have really strong innovation programs and GenAI leadership to be offering some of that as a service to their clients—many of whom have small legal teams and don’t have the ability to think through what all of this means.
Bridget McCormack: They don't have the time or the resources, but they know they need to do it.
Jen Leonard: And imagine having a firm that reaches out and says, “We’ve developed this AI academy,” or “We’re workshopping different pilot projects, and we’d love you to come in and send some of your team to give us feedback—and also to learn with us.” I think that would be really well received.
But I think, to the point about the innovator’s dilemma, people are so focused on what they need to do today—it’s really hard to find the bandwidth to make that happen.
Bridget McCormack: Yeah, I think it’s very hard for lawyers to blue-sky anything for really, I think, good reasons—cultural and legal reasons. We are so wedded to what’s happened before that it is very hard to say, “What if we weren’t bound by any of that? What could it look like?”
For me, one of the ways that helps is to talk to people on my team who are not lawyers. Also, not always comfortable for lawyers—to have non-lawyers who are equal partners in designing their future together. But, I mean, you’ve talked to Diana from my team, who’s not a lawyer, but she’s a brilliant thinker. I mean, she runs our engineering department, so she’s a talented technologist, but she’s much more than a technologist, right? She’s a strategist. She’s an amazing thought partner with me in a way that I worry, you know, if I didn’t have a Diana—if I was only talking to lawyers all the time—would it be harder to see what a blue-sky future looks like, right?
Jen Leonard: Yeah, I think people who have an entrepreneurial mindset right now are super excited. Like you—I wake up every morning and it's like, “I wish I could use AI to clone myself so that I could look at ten different things all day long and figure out what they mean.”
And in my life, I went from spending 20 years surrounded by lawyers and professors and judges to being a small business owner and going to events for entrepreneurs. And it is fascinating. Oh my gosh—everything is possibility.
And I think that the blend of the two—blue-sky thinking that is deliberative and involves critical thought—is the unlock here. And to your point, it’s a cultural change for lawyers to recognize that they’re not the only ones that bring value to the table.
Bridget McCormack: And I think the ones that realize that will have a leg up. You need people other than lawyers at your strategy table. You really do.
Jen Leonard: Definitely. And we’ll just end by saying that if law needs some evidence that they should take this seriously—this upskilling and leadership—we have some statistics here from Microsoft. Brad Smith from Microsoft wrote a really interesting piece called The Golden Opportunity for American AI. And in it, he talks about how Microsoft alone, in 2025 alone, has pledged to train 2.5 million American students, workers, and community members with AI skills—for new jobs, pursuing new careers, and building new businesses.
And there are lots of other statistics about investments from companies like Amazon and all the other big tech companies. And I always look to them—not necessarily to emulate them—but as a signal as to where we’re headed in the jobs landscape. So I thought that was really interesting.
And my big takeaway from all of this is that 2025, like you said, it might not look that different in terms of the data that we see next year, and it might not feel that different to a lawyer day-to-day—but to me, it feels like a pivotal year. A year where leaders in firms, in corporate legal—everywhere—have to make a choice as to whether they’re going to try to adhere to the old world and hope that they make it to retirement, I guess…Or they’re going to read the writing on the wall and develop a strong strategy and guide their firm into the future—which sounds like a lot more fun to me. What do you think?
Bridget McCormack: Yeah, I mean The New York Times broke this afternoon that the president is going to be announcing a $100 billion investment—and I guess it’s mostly AI infrastructure. But that kind of investment, to make sure America maintains its lead in this general-purpose technology that’s going to change the world—together with the kinds of announcements like the one from Brad Smith—and I feel like we heard another one from OpenAI as well about just investment in general education around AI literacy.
The rest of the world is going to figure it all out. You know, I guess maybe they’ll stay away from the law books—but, you know, those Meta glasses? Like, you can go in the library and just take pictures of all the laws. So I’d rather have the lawyers leading what this looks like in legal.
And so I’m excited for what happens in legal and strategy and thinking about what might be possible in 2025. I do think we’ll see some big changes.
Bridget McCormack: Same. This was such a fun conversation.
Jen Leonard: And thanks to everybody out there for listening. We look forward to seeing you on the next episode of 2030 Vision: AI and the Future of Law. Take care!