Jen Leonard: A Journey Through Innovation, AI, and Education

In this episode of This Legal Life, host Ben Chiriboga engages with Jen Leonard, founder of Creative Lawyers and former Chief Innovation Officer at Penn Carey Law. The conversation spans Jen’s dynamic career journey, from her roots as a litigator to her current role driving change in the legal profession through innovation and education. Jen shares insights on the transformative potential of generative AI, the importance of diverse professional networks, and how design thinking can reshape the future of legal services. This episode is a masterclass in resilience, creativity, and embracing change in an evolving industry.

Guest Bio:

Jen Leonard is the Founder of Creative Lawyers, a company dedicated to supporting law firms, corporate legal departments, and courts that understand the urgency to modernize practice and services. Jen works with leaders to cultivate innovative cultures, build nimble strategies to navigate a volatile environment, and promote mindsets that drive change. She leads design thinking workshops, facilitates innovation challenges, delivers retreat keynotes, provides ongoing strategic support, designs educational Generative AI content, and offers structured events that help lawyers reflect on their careers as they build the next stage in their journey.

Before launching her company, Jen was the first Chief Innovation Officer and Executive Director of the Future of the Profession Initiative at Penn Carey Law. She practiced law for ten years after graduating from Penn Carey Law in 2004 and before returning to build the Law School’s Center on Professionalism, which became a nationally-recognized law student professional development program.

At Penn, she teaches Generative AI in Law Practice, Design Thinking for Lawyers, Modern Law Firm Business and Innovation Strategy, and Attorney Well-Being as Ethical Obligation. She has also taught design thinking and ideation techniques to industry leaders in Wharton’s Executive MBA program and Penn Nursing’s Summer Innovation Institute.

Jen is a Fellow of the College of Law Practice Management, a member of Penn’s Inn of Court, served on NALP’s Driving Inclusion Task Force, and received Penn’s Beverly Edwards Award for Exceptional Leadership. The American Bar Association honored Jen in its 2024 list of Women in Legal Tech. She also serves on the Board of Pro Bono Institute.

Jen hosts several podcasts about the legal profession, including 2030 Vision: AI and the Future of Law (co-hosted with the President & CEO of the American Arbitration Association, Bridget McCormack), Law 2030, Future-Proofed (co-hosted with Kirkland’s Chief Innovation Officer, Rachel Dooley), and Practising Law Institute’s Fast-Tracked: Emergent Issues in the Legal Profession. She writes and speaks frequently about innovation and the legal industry’s future.

Links:

http://www.creativelawyers.net/

https://www.youtube.com/@2030VisionPodcast