AI is fundamentally reshaping how lawyers work—and how we should be training them to work. These aren’t separate challenges. The lawyers best equipped to leverage AI tools effectively are those who understand what skills remain distinctly human, what tasks should be delegated, and how to maintain quality and judgment in an AI-assisted practice.
This session brings together practitioners and platform builders who are working on these questions daily. We’ll begin with lightning talks—brief, focused insights from key players who will share one concrete lesson they’ve learned about training legal professionals to use AI effectively or rethinking legal education for the post-AI era. No lengthy pitches, just the hard-won lessons from the field.
Following the lightning round, our expert panel will dig deeper into the most pressing questions: What does effective AI training actually look like? How do we measure whether lawyers are using these tools well? What skills become more important, not less, in an AI-augmented practice? And how should law schools and firms rethink their training programs to prepare lawyers for this shift?
You’ll leave with practical frameworks, honest assessments of what’s working (and what isn’t), and connections to others navigating the same transformation.
Event Timeline
- 6:00 p.m. – Networking over food and drink
- 🎉 Our networking hour will serve as cross-over reception with the Legal Innovators conference taking place at Latham earlier that day.
- 7:00 p.m. – Introductory remarks and community intros
- 7:15 p.m. – “Lessons Learned” lightning talks from builders in the thick of it, including:
- Abdi Shayesteh, AltaClaro
- Tony Capecci, Haynes & Boone
- Adam Stofsky, Briefly
- Christian Lang, Lega
- 7:30 p.m. – “Rethinking Legal Training in the Age of AI” panel (see below)
- 8:30 p.m. – Wrap-up; continued networking
Panelists

Matthew McConnell
Associate Director of Artificial Intelligence - Practice Innovation, Latham
Matthew McConnell is the Associate Director of Artificial Intelligence and Legal Innovation at Latham & Watkins, where he leads the Platforms & Operations function and guides the firm’s integration of generative AI and leading legal-tech into everyday practice. Prior to joining Latham, Matthew led global innovation programs at White & Case.

Heidi Brown
Associate Dean for Upper Level Writing, New York Law School
Professor Heidi K. Brown is a graduate of the University of Virginia School of Law, Associate Dean for Upper Level Writing at New York Law School, and a former litigator in the construction industry. She has been a professional legal writer for 31 years. Heidi is the author of a three-volume legal writing textbook series called The Mindful Legal Writer. Since 2023, Heidi has designed courses, workshops, webinars, and CLEs on Generative AI literacy, “prompt engineering,” and the ethical and responsible incorporation of GenAI tools into the legal research and writing workflow. Heidi is also the author of three books about well-being for law students and lawyers–The Introverted Lawyer, Untangling Fear in Lawyering, and The Flourishing Lawyer–and a new travel memoir called The Map I Draw: A Memoir of Travel as a Passport to Self.

Felicity Levey
Director of Practice Innovation, Cooley
Felicity leads various innovation initiatives at Cooley as the director of practice innovation. In this role, she partners with attorneys to explore and implement emerging technologies – especially artificial intelligence (AI) – to transform how legal services are delivered and elevate the attorney and client experience. Her work focuses on incubating new tools, driving adoption and building the next generation of legal practice at the firm.
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