Episodes

Justice Jerod Tufte on AI in the courts, judicial workflows, access to justice, and why human judgment must remain central.

Jen Leonard and Bridget McCormack on Big Law’s shift from AI adoption to AI building, junior attorney development, and why AI strategy has to match firm strategy.

Farrah Pepper and Kirsten Talmage on PLI’s AI competency framework, legal training, professional development, and the skills lawyers need in the AI era.

John Nay on agentic law, AI-native legal services, AI agents, outcome-based pricing, and the future of legal work.

Nick Fleisher on AI-native legal infrastructure, legal operations, agentic workflows, and the future of in-house legal teams.

Sharon Crane joins Jen Leonard and Bridget McCormack to discuss Unprecedented, law firm transformation, AI, legal education, and designing human-centered legal organizations.

Nikki Shaver on legal tech growth, AI-native firms, agentic AI, and how law firms are rethinking value, pricing, and strategy.

Bridget McCormack on Legal Context Protocol, agentic commerce, and why AI agents need legal infrastructure.

Daniel Schwarcz on new research into AI, legal reasoning, and how lawyers learn.

What the latest Am Law 100 power rankings reveal about competition, client demand, and the future structure of Big Law.

How AI agents, contract data, and system design are reshaping legal work and the role of the lawyer.

When AI-generated legal advice triggers a lawsuit—and what Legalweek reveals about ROI, adoption, and governance.

Artificial intelligence is beginning to reshape one of the most foundational areas of legal practice: contract law.

In this episode, Jen Leonard and Bridget McCormack are joined by Professor Dave Hoffman (University of Pennsylvania Law School) to explore how tools like Claude are influencing contract interpretation, legal research, and legal education. They discuss how AI can help judges interpret ambiguous language, what it means for the value of transactional lawyers, and why defining an “AI-...

AI recording tools can make lawyers more efficient—but what are the risks to confidentiality?

In this episode, Jen Leonard and Bridget McCormack examine how AI recording tools intersect with attorney–client privilege, professional responsibility rules, and the evolving skill demands of an AI-driven workforce.

Topics discussed include:
How AI recording platforms may introduce third-party privilege risks

State consent laws and the ethical limits of secret recording

New York Bar Formal Opinion ...

As the legal profession enters 2026, the conversation about AI is shifting. It is no longer about awareness or early adoption. It is about measurable impact.

In this episode of AI and the Future of Law, Jen Leonard and Bridget McCormack are joined by Zach Abramowitz for a legal market check-in on AI agents, ROI, competitive pressure, and the widening divide between AI superusers and skeptics.

They discuss:

The shift from AI assistants to AI agents

Why 2026 is about measuring ROI, not experim...

What happens when lawyers stop waiting for permission and start building with AI? Jen and Bridget explore the rise of creative associates and what tools like Claude Code reveal about the future of legal work. From agentic AI systems that refactor how coding gets done to junior lawyers who “vibe-code” solutions to everyday firm problems, this conversation looks at how innovation is increasingly bottom-up in law firms.

Topics covered include:

Claude Code and agentic AI for knowledge work

Why cr...

Can lawyers really trust AI—and what does “trust” mean in modern legal practice?

In this episode of AI and the Future of Law, hosts Jen Leonard and Bridget McCormack are joined by Gabe Pereyra, President and Co-Founder of Harvey AI, to explore how generative AI is moving from a productivity tool to core infrastructure for law firms.

Gabe explains how leading firms are deploying AI at scale, why hallucinations are no longer the central concern, and how governance, auditability, and human-in-the...

Private equity interest in U.S. law firms is accelerating, and AI is a major reason why. In this Season 3 kickoff, Jen Leonard and Bridget McCormack explore how ethics rules collide with the capital demands of AI, and why the real story isn’t short-term profits but long-term investment in legal infrastructure. They unpack Rule 5.4, the rise of the MSO model as a workaround for outside investment, and what “ownership” really means when control over data, technology, and professional judgment is a...

What will AI actually change in law by 2026—and how should firms, courts, and legal institutions prepare? In this season two finale of AI and the Future of Law, hosts Jen Leonard and Bridget McCormack step back from the hype cycle to offer grounded, practical predictions about the next few years.

They explore Google’s Gemini 3 and the shift from chatbots to agentic systems, the “platformization” of legal services driven by MSOs, ALSPs, and private equity, and the new talent demands this creates...

How can AI expand access to justice for the millions who can’t afford a lawyer? In this episode, hosts Jen Leonard and Bridget McCormack speak with Sateesh Nori and Tom Martin about AI tools reshaping legal help, including Depositron for security deposit disputes and Law Answers AI for jurisdiction-specific guidance.

They discuss Sateesh’s journey from housing court to AI innovation, Tom’s work building scalable solutions for the public, and the profession’s ongoing debate over “second-tier jus...

Is AI making legal writing too easy—and too cheap? In this episode, Jen Leonard and Bridget McCormack explore how generative AI tools are reshaping writing as a professional skill. They discuss the paper “Making Talk Cheap,” which argues that when anyone can generate polished text, writing loses its value as a signal of skill, effort, or merit. What does this mean for hiring, advancement, and lawyering in the AI era? Plus, they unpack a new Wharton study showing how enterprise AI use is soaring—...

Can AI make the nation’s largest trial court more accessible, trusted, and just? In this episode, LA Superior Court CEO, David Slayton joins hosts Jen Leonard and Bridget Mary McCormack to unpack how generative AI is already reshaping court services—and why “effective” beats “efficient.”

We explore Court Help on LACourt.gov, change-management tactics that stick, and the delicate balance between moving too slowly (and getting overwhelmed) and too fast (and losing public trust). Practical, candid...

Can an AI fairly decide a dispute—and win party trust? Recorded live at MAICON 2025, this episode dives into the American Arbitration Association’s first AI arbitrator, a documents-only two-party workflow designed for construction cases with a human in the loop. AAA President Bridget McCormack explains the multi-agent architecture, why procedural fairness matters, and how the tool reflects a century of arbitration expertise. We also unpack OpenAI’s Sora 2 rollout, likeness/IP controversies, and ...

How should law schools teach judgment, writing, and readiness in the age of AI? Georgetown’s Jonah Perlin and Suffolk’s Dyane O’Leary join hosts Jen Leonard and Bridget McCormack to explore how generative AI is reshaping legal education—from 1L writing and grading to ethics, policy, and professional judgment.

They share real classroom experiments that reveal how professors are using AI to teach reasoning and curiosity, and how schools are balancing innovation with integrity through redesigned a...