Jen examines accelerating trends reshaping the legal profession, leads the development of related thought leadership projects, and teaches developing lawyers how to adopt a mindset that embraces ambiguity, innovation, and creativity. She teaches Modern Law Firm Business Strategy and Design Thinking for Lawyers at Penn Law and speaks, writes, and teaches to promote diversity, inclusion, and well-being in the profession. Jen's previous roles include Penn Law's Associate Dean for Professional Engagement, Director of its Center on Professionalism, and ten years in private-sector and government legal practice.
We recently spoke with Jennifer Leonard, chief innovation officer at the University of Pennsylvania Carey Law School and executive director of the school’s Future of the Profession Initiative to discuss innovation in the law. Jennifer sat down with Rachel Dooley, interim managing counsel for McKinsey Digital to talk about the efforts Jennifer’s using to help transform how legal services are delivered—starting at the law-school level—and why she’s excited about changes ahead. Read the full interview below.
Rachel: Jennifer, I’m thrilled to talk to you today! A mutual friend put us in touch and we instantly connected on the promise of what the legal profession could be and become, and how great it could be to be a lawyer.
Is there anything that excites you in seeing what’s happening in the industry—like how lawyers practice at McKinsey or elsewhere—where creativity and innovation is headlining?
Jennifer: I love how McKinsey thinks about trust between lawyers and clients as developing “connective tissue” that promotes partnership across the life of a project rather than what happens so frequently: lawyers coming in only at the end of an endeavor.
In that scenario, the lawyer is sometimes forced to counsel the client to alter the project because of legal issues that a more connected, ongoing partnership would have unearthed earlier. This can frustrate the client and contributes to the general counsel’s reputation as being the “no” department. What McKinsey does through things like tech trust teams is be explicit about shifting the mindset of attorneys and clients so they work collaboratively. This approach can strengthen firm projects, use resources more efficiently, and clarify the value in working as a team for both lawyers and clients.
Rachel: Can you tell us about your role at Penn Law?
Jennifer: In my opinion, I have the coolest job of any law school in the country. My main responsibilities are to develop a deep understanding of the many changes affecting the legal profession; cultivate a community of people interested in solving the problems facing the legal industry in new ways; teach courses that prepare students and graduates to thrive in an ambiguous future full of opportunity; and launch thought-leadership projects that demonstrate Penn Law’s eagerness to contribute to the reshaping of the next chapter of legal services. My colleagues and I advocate for change, teach developing lawyers, and lead conversations that amplify new voices from the profession to transform the way we deliver legal services.
Rachel: So, you help mold the next generation of lawyers—why are you drawn to that work?
Jennifer: Because of what I see in so many of the students we serve: bright young people who want to make the world better by leveraging the power of a law degree. In practice, so many lawyers find themselves burned out, frustrated, and working on tasks that are misaligned with the things that light them up and drew them to law in the first place. That was certainly the case for me. If our systems worked perfectly, I would say those unhappy lawyers were simply in the wrong line of work, but that’s not the case. So many things in our profession demand a reboot. I’m so thrilled to help a generation of talented professionals on the rise who aren’t yet indoctrinated into doing things “the way they’ve always been done” develop new solutions to make our society healthier, promote confidence in the rule of law, and allow our graduates to express their full humanity in practice and life. And the great news is they are about a million times savvier and smarter than I was when I arrived at law school; they are eager to respond to the challenges ahead.
Rachel: What excites you about the future of the legal profession? What do you think still needs to change?
Jennifer: I’m excited that we’re finally having conversations that are long overdue, like: Why can’t lawyers be professionally satisfied and have time for family, friends, and hobbies? Why are legal services inaccessible to the people and small businesses that need them? Why isn’t the legal profession more representative of the diverse society it is supposed to serve? And finally, why are lawyers consistently portrayed as antiquated naysayers rather than the sophisticated and talented problem solvers they’re perfectly poised to be? Now, not a day goes by when the major legal publications aren’t laser-focused on these issues, and that excites me.
I’m also excited that different generations of lawyers are eager to reshape the legal-services landscape. If it were just law students demanding innovation and progress, I would worry that the generations ahead of them might dilute their passion and enthusiasm and risk losing their skills, intelligence, and creativity. But so many people—from lawyers who occupy the most important positions in the profession to people sitting down to take the LSAT—want to be part of generational change. This cross-generational drive for change creates the perfect conditions for innovation and progress.
Rachel: You have spoken about mental health in the profession. What do you see coming next with regards to mental health? Why is it important?
Jennifer: I struggled a great deal with depression and anxiety in law school and my early years of practice. I was ashamed of how inept I thought I was, and I carried that shame and anxiety around for too long. But it turns out I wasn’t incompetent—I was simply inexperienced.
Maybe more than any other topic, I’m excited that the lawyer well-being movement has really taken hold since the Hazelden-Betty Ford study in 2016 and the National Task Force Report that followed. Our profession needlessly hemorrhages talent at every opportunity. What if we instead nurtured that talent and put it to work to solve the many problems we face?
With respect to what’s next, I share my students’ hope that we move beyond thinking about how individuals respond to unhealthy stressors. I want to see us move into a conversation about how to transform toxic environments so lawyers can spend less time arming themselves with defensive techniques and more time contributing to solving problems.
Rachel: In your experience, what gets students in law school / lawyers in the making most excited about practice?
Jennifer: They want to be part of an inclusive industry that brings all its talent to bear, and they will accept nothing less. And that shift is what will strengthen our ability to innovate and better serve our clients and the broader world, so I encourage them to keep pushing.
By and large, they are a generation that has come of age in a time of social tumult and accelerating technology. They also aren’t afraid to experiment and learn. I always tell my students they’re the first generation of living lawyers who can’t look to the lawyers that came before them for a roadmap to success. They will need to chart a new path, both individually and as a group. They don’t find this idea troubling; instead, they are excited to modernize the practice and make real strides in the reputation of the legal profession and the service it provides to clients.
Rachel: What does innovation mean to you, and how does it play a role in your work?
Jennifer: Innovation to me simply means finding new ways to solve problems that create value. The value can be financial, psychological, social—but there must be some “value add.” I love innovation because it’s not a buzzword or something only a few natural creatives among us can achieve. We can teach, nurture, measure, and improve the process of innovation to bring great ideas forward. It also isn’t limited to technology, though most of the ink spilled focuses on technology. Innovation can also be very low tech, featuring small changes that add value.
And innovation in legal requires unlikely sources to inspire lawyers. Now that I have learned about the process of innovation from some of the leaders in the field at Wharton, I see inspiration everywhere. What if litigants in a courthouse saw a screen that listed the estimated start time and location of their matters like an airport arrivals and departures window? What if a new class of paraprofessionals could provide legal service for lower-complexity matters? What if the profession could serve more people, like in the healthcare industry? What if legal became more like the field of psychology, expanding access to counseling through virtual consultations and third-party funders? I mean, the sky really is the limit, and it takes so little to get the creative juices flowing.
Rachel: What does creativity mean to you, and how does it play a role in your work?
Jennifer: Creativity is probably what most excites me about the future of legal because, as a profession, we have neglected it for so long. I believe it’s the key to our industry’s future. When we think of creativity in lawyering, we think of making novel arguments about the law itself. Important, but not what excites me. Creativity means unleashing different parts of our minds, thinking in nonlinear ways, generating many wild ideas to find one breakthrough innovation that changes everything…
And, in addition to unlocking solutions to the many increasingly urgent problems that face this profession, creativity contributes to well-being and connection with others. I was responding to a journal prompt recently that asked, “What three things you would do if you retired tomorrow?” All my answers related to creativity: start a new business, sign up for a tap-dancing class, shadow a celebrated interior designer. Am I a brilliant creative? No, but all the things that gave me that elusive state of flow growing up were creative. As we get older and more serious, we let go and think of them as childish pursuits. But what if the parts of our brains we force to be dormant as serious lawyers are the very parts we most need to solve the problems we face? That is exciting!
Rachel: What are your three “best evers?”
Jennifer: Best bite of food ever: When I was in fourth grade, we went to the Delaware shore. I was assigned to deliver an instructional presentation for my class. Much like me as a parent, my parents forgot about the assignment until we were leaving, so they bought a bushel of Maryland crabs and taught me how to clean them, which is the presentation I delivered to my classmates. To this day, my hands-down favorite meal is a bushel of fat, hot Maryland crabs prepared with Old Bay seasoning, drawn butter, and plenty of lemon, rolled out on brown paper and paired with an ice-cold beer—which I clearly didn’t feature in my classroom presentation! Is there anything better?
Best sound or song ever: ELO’s Mr. Blue Sky is my favorite song. I can’t help but smile when I hear it even if I’m in a rotten mood. Plus, it offers so many great air drumming opportunities.
Best visual or color that never fails to bring you joy: During the pandemic, I’ve been able to pick my son up from first grade each day and take him to the playground after school. I am fascinated watching him play with his friends and grateful to have the chance to see him grow. Kids are completely free. They never think about what they’re supposed to be doing (sometimes to my extreme frustration). They just experiment with each other—walking up slides backward, hanging from tree limbs, making up games on the fly, talking in funny voices. Their happiness and full-contact engagement is stunning, and it makes me deeply sad that over time, we abandon the very traits that could make us highly engaged, fulfilled, and productive adults. My goal is to bring some of that joy, flow, creativity, and full-bodied, full-throated passion to a profession in need of new solutions.