Q&A: Jen Leonard on Unprecedented and the Future of Law

At a recent Practising Law Institute event celebrating the publication of her book, Unprecedented, Jen Leonard sat down for a Q&A to discuss the challenges and opportunities reshaping the legal profession. Leonard, Chair of PLI’s Innovation Council, explored how law firms can respond to AI, evolving client expectations, and talent development challenges. The following edited Q&A highlights key insights from their conversation.

What led you to write Unprecedented, and why did you choose to tell it as a story rather than a traditional business book?

At first, I tried to write a very straightforward business book about the changes in the profession, the history of legal practice, and frameworks for innovation. But when I read it, I thought, “I wouldn’t even want to read this.” It was too dry. Then I tried a version focused on AI and existential change, with a metaphor about a comet coming toward Earth and dinosaurs not seeing it coming. That was too weird.

The breakthrough came when I realized I could tell the story of a law firm going through a five-day retreat. At first, I thought no law firm would ever take that much time away. But then I needed an inciting event that would make such a retreat believable. With so much consolidation happening in the legal industry, I imagined a culture-driven firm under pressure to be absorbed by a much larger firm with a very different identity. That gave the story urgency.

The book includes a number of fictional characters. Were they inspired by people you have encountered in your work with law firms?

Definitely. The characters are composites of people we meet all the time in our work with law firms.

One of my favorite characters is Robert Kim, a senior partner who has spent his entire career at the firm. He is practical, logical, and very heads down. Over the course of the retreat, he begins to realize that when people are talking about succession planning and the future of the firm, he may not really be part of that future. He was inspired by a partner I met at a law firm retreat who was preparing to retire and told me he could not imagine what he would do with his life because he had been practicing law for 45 years.

I wanted to contrast Robert with William Klept, the rainmaker partner who is doing very well in the current system and does not really want to change. He represents the people who have been successful under the existing model and understandably question why the firm should disrupt it.

The junior associates were also important. Alex is tech-forward, enthusiastic, entrepreneurial, and eager to use new tools. But he is surrounded by other junior associates who are anxious about what technology means for their jobs, their development, and their critical thinking.

What makes this moment different from earlier periods of change in the legal profession?

After the 2008 financial crisis, the relationship between law firms and clients changed. Clients demanded more for less, legal operations grew inside corporate law departments, and technology became more sophisticated, especially in litigation. There was innovation, but often it did not really touch the core business model.

Generative AI changes that. It accelerates all the underlying dynamics and makes them much more real. It intersects with regulatory reform, pricing pressure, talent development, hybrid work, and client expectations.

At the same time, hybrid work has made mentoring junior associates more difficult. Add AI to that, and firms are asking how they will develop judgment, critical thinking, and professional identity in lawyers who may be doing less of the traditional junior-level work. What feels different now is that top leadership is engaged. Chairs and managing partners are saying, “We need to figure this out.”

A major framework in the book is design thinking. How does that apply to law firms?

Traditionally, experts design systems for the people they serve without really consulting those people. Design thinking asks us to begin by understanding the human beings on the receiving end. That might be a client, an associate, a self-represented litigant, or even another department inside the firm.

The goal is to move beyond assumptions. Lawyers are comfortable delivering memos, advice, and hourly services in familiar ways. But did the client ask for that format? Or are we just repeating what the system taught us?

Design thinking helps firms define problems differently, generate more creative solutions, and build services around the people they are trying to serve.

You describe the future law firm as “human-centered.” What does that mean?

A human-centered law firm confronts major changes, including AI, regulatory reform, new business models, and multigenerational workforces, while keeping human beings at the center.

If firms look at technology only as a way to replace people, reduce headcount, or save costs, they risk damaging their cultures. The better question is how technology can augment human skills.

A human-centered firm asks: What do our clients need from us as people? What do our associates need to develop? How do we use technology to strengthen the best human parts of our work, rather than erode them?

What do you hope changes in legal education and lawyer development over the next decade?

I hope we are forced to solve a problem that has existed for a long time. Law firms have historically relied on clients to subsidize the learning process for junior lawyers. But if AI changes the economics of entry-level work, firms will no longer be able to bill for learning in the same way.

That means we need to rethink how lawyers are trained before they arrive at firms and after they get there. My hope is that new models emerge. Maybe third parties help firms build better training systems. Maybe new career paths open up for law graduates who want to use different skills. Most of all, I hope the profession becomes healthier.

We have had a crisis in lawyer well-being for a long time. We have lost too many talented people because of the conditions in which lawyers work. If new models allow people to spend more time mentoring, using judgment, and doing meaningful human work, then maybe we can create a profession where more people can thrive.

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For more information about Jen Leonard’s new book, ‘Unprecedented: Designing a Human-Centered Law Firm When Everything Is Changing,’ please see here.

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[ This is a sponsored book promotion by PLI for Artificial Lawyer. ]