AI and the Future of Law

How is AI changing the work of in-house legal teams? In this episode, Jen Leonard and Bridget McCormack are joined by Nick Fleisher, co-founder and CEO of Sandstone, an AI-native platform built specifically for in-house legal teams. Nick discusses how AI is transforming legal operations by helping legal departments manage intake, triage work, connect business context, and move from reactive servic...

Can law firms redesign themselves for a world shaped by generative AI? In this episode, Jen Leonard and Bridget McCormack are joined by Sharon Crane, president of Practising Law Institute, for a conversation about Jen’s new book, Unprecedented: Designing a Human-Centered Law Firm When Everything Is Changing . Together, they explore why law firm transformation is difficult, how storytelling can mak...

The legal tech market is growing fast—but is it a bubble, or the beginning of a new era for legal services? In this episode, Jen Leonard and Bridget McCormack are joined by Nikki Shaver, co-founder and CEO of Legaltech Hub, to discuss how AI is reshaping law firm strategy, pricing, technology selection, and competition. Nikki explains why firms are moving beyond efficiency as the main measure of A...

What happens when AI agents start making contracts with other AI agents? In this episode, Jen Leonard and Bridget McCormack explore Legal Context Protocol, or LCP, a new open protocol designed to help legal terms become discoverable, verifiable, and connected to agentic transactions. Bridget explains why existing e-commerce legal infrastructure may not translate cleanly to a world where machines n...

Can AI help lawyers learn—or does it weaken the skills legal training is meant to build? In this episode, Jen Leonard and Bridget McCormack are joined by Daniel Schwarcz, Fredrikson & Byron Professor of Law at the University of Minnesota Law School, to discuss new empirical research on artificial intelligence and human legal reasoning. Daniel explains a randomized control trial studying how la...

The latest Am Law 100 power rankings reveal a legal industry undergoing rapid transformation—driven by shifting demand, intensifying competition, and the growing influence of AI. In this episode, Jen Leonard and Bridget McCormack are joined by legal industry analyst Jae Um to break down what’s changing in Big Law. They explore the rise of “apex predator” firms, widening performance gaps, evolving...

Artificial intelligence is moving beyond tools and into systems—reshaping how legal work is performed and delivered. In this episode, Jen Leonard and Bridget McCormack speak with Jason Barnwell, Chief Legal Officer at Agiloft, about the rise of AI agents, contract lifecycle management, and what these shifts mean for legal practice. They explore how some professionals are able to extract exponentia...

Artificial intelligence is beginning to test the boundaries of legal practice itself. In this episode, Jen Leonard and Bridget McCormack examine Nippon Life v. OpenAI , a lawsuit alleging that a chatbot engaged in the unauthorized practice of law by generating legal advice, drafting filings, and influencing litigation strategy. The case raises foundational questions about liability, regulation, an...

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...

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...

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. The...

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 bot...

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...

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,...

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”...

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 bu...

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 lawy...

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 betw...

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 centu...

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 re...

Can state‑court judges safely use generative AI? In this episode, Jen Leonard and Bridget McCormack unpack Pennsylvania’s interim policy for courts—what it allows, what it restricts, and how human review and confidentiality guardrails work in practice. They compare real AI workflows from their own desks—editing a book with Claude and turning a long essay into slides—and dissect the “AI pilots are...

What does it take to modernize a 100-year-old legal institution and prepare lawyers for the AI era? In this episode, Jen Leonard and Bridget McCormack sit down with Jae Um (Lumio) and Ilona Logvinova (Cleary Gottlieb) to explore how legal organizations move from AI experiments to real impact. From acquisitions and change management to digital agents and legal education reform, this conversation br...

Is GPT-5 good enough to practice law? This episode dives into OpenAI’s newest model and its implications for legal practice, including how it compares to previous models and where human oversight remains essential. Jen Leonard and Bridget McCormack also unpack a groundbreaking report from IAALS on regulating AI in legal services, shifting the focus from lawyers to consumers. Episode Highlights: (2...

What happens when a litigator and a quantum physicist build a law firm from the ground up with AI at its core? In this episode, hosts Jen Leonard and Bridget McCormack speak with Phillip Young and Daniel Long of Garfield Law, the UK’s first fully AI-native, regulator-approved law firm. They share how Garfield streamlines small debt claims, navigated unprecedented regulatory scrutiny, and solved AI...

Could AI make you a better advocate than a lawyer? In this episode, Jen Leonard and Bridget McCormack explore real-world stories of self-represented litigants using AI tools to win cases, plus a bold proposal to allow “robot lawyers” in appellate arguments. From century rides powered by ChatGPT to experiments in legal education innovation, this conversation tackles the evolving role of AI in justi...