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AI agents are moving beyond answering questions to taking action. But what happens when AI can make decisions, complete tasks, and interact with other systems on its own? And what does that mean for lawyers? In this episode of AI and the Future of Law, Jen Leonard and Bridget McCormack explore the rise of agentic AI and its implications for legal practice. They share their experiences using Instinct, a personal AI assistant, discuss JEV and the possibility of AI verifying other AI systems, and examine how autonomous technology is changing the way lawyers work. From supervising AI agents like junior associates to managing AI training fatigue, Jen and Bridget consider the opportunities, challenges, and professional responsibilities emerging as AI becomes more autonomous. Key Discussion Points How AI agents differ from traditional chatbotsPersonal AI assistants and AI verification toolsSupervising AI agents and managing their actionsAI adoption, training fatigue, and law firm leadershipProfessional competence, ethics, and accountabilityAI and the Future of Law is hosted by Jen Leonard and Bridget McCormack. A Creative Lawyers Podcast, sponsored by Clio. https://www.aiandthefutureoflaw.com/ Hosted on Acast. See acast.com/privacy for more information.

Season 4 of AI and the Future of Law begins with one of the most unsettling AI stories of the year: the Hugging Face incident, involving reports that OpenAI agents escaped a training sandbox, coordinated with one another, and accessed external systems. In this episode, Jen Leonard and Bridget McCormack unpack what happened, why it captured so much attention, and what it reveals about the next phase of AI safety, cybersecurity, and governance. They discuss how autonomous agents can create new risks for courts, law firms, legal departments, and the clients lawyers advise. The conversation also explores why AI governance cannot be treated like a one-time software approval. As frontier models become more capable, legal institutions will need ongoing oversight, stronger vendor diligence, better documentation, and practical systems for managing risk. Key topics include: The Hugging Face incident and why it mattersAutonomous AI agents and cyber riskAI governance beyond one-time approvalWhat courts and law firms should be watchingVendor diligence, documentation, and accountabilityWhy lawyers have a role in shaping AI oversightThroughout the episode, Jen and Bridget move beyond the headlines to focus on what lawyers should be thinking about now: accountability, cyber risk, regulation, courts, governance, and the legal work ahead. Hosted on Acast. See acast.com/privacy for more information.

Season 3 of AI and the Future of Law explored a legal profession moving quickly from AI experimentation to real transformation. In this special recap episode, we revisit some of the season’s most memorable conversations about legal AI, agentic systems, law firm strategy, AI-native business models, professional competency, and the role human judgment will continue to play as the technology advances. Thank you to everyone who listened, followed, shared, and joined us throughout Season 3. AI and the Future of Law will return in October with Season 4 and more conversations about how artificial intelligence is reshaping the legal profession and the world around it. Subscribe on YouTube, follow the show on your favorite podcast platform, and leave a review if the conversations have been helpful to you. Hosted on Acast. See acast.com/privacy for more information.

How can judges use AI without delegating the human judgment at the center of their role? In this episode, Jen Leonard and Bridget McCormack are joined by Justice Jerod Tufte of the North Dakota Supreme Court for a conversation about AI, judicial workflows, public legal data, access to justice, and the future of courts. In this episode: How judges can use AI while preserving human judgmentWhy AI should support, not decide, judicial workHow AI can assist with records, citations, and bench memosWhy courts need guardrails for AI useHow AI may increase litigation volumeWhy public law should be accessible and AI-ready Hosted on Acast. See acast.com/privacy for more information.

What does Kirkland & Ellis’ $500 million AI bet mean for Big Law — and for junior lawyers? In this episode, Jen Leonard and Bridget McCormack discuss Kirkland’s reported investment in building its own proprietary AI platform and what it signals about the legal industry’s shift from AI adoption to AI building. They explain why Kirkland’s strategy may make sense for Kirkland, but why other firms should be careful not to copy it without considering their own strengths, clients, culture, and market position. Jen and Bridget also explore growing concerns about junior attorney development as AI takes on more entry-level legal work. If junior lawyers are no longer learning through the same kinds of assignments, how will firms help them build judgment, confidence, and expertise? And what new training models might emerge? The episode also includes an AI Aha! segment on practical AI use cases in everyday life and a What Just Happened discussion on Anthropic, model risk, and emerging government oversight of frontier AI systems. In this episode: Kirkland’s $500 million AI announcementBig Law’s shift from AI adoption to AI buildingWhy AI strategy should match firm strategyWhat AI means for junior associate developmentWhy learning by doing does not happen automaticallyHow firms might rethink legal trainingWhat Anthropic’s model-risk episode means for lawyers and clients Hosted on Acast. See acast.com/privacy for more information.

What does it mean to be an AI-ready lawyer? In this episode, Jen Leonard and Bridget McCormack are joined by Farrah Pepper, legal innovation partner at Harvey, and Kirsten Talmage, chief strategy officer at Practising Law Institute, to discuss The AI-Ready Lawyer: A Competency Framework for the AI Era. Farrah and Kirsten explain why the legal profession needs a shared language for AI competency, how the framework can help law firms, legal departments, law schools, and individual lawyers, and why AI training should focus on durable professional skills rather than any single tool. The conversation also explores new legal career paths, the importance of oversight and judgment, and how organizations can use the framework to assess training gaps and build AI fluency responsibly. In this episode: What it means to be an AI-ready lawyerWhy the legal profession needs a shared AI competency frameworkHow AI fluency differs from tool-specific trainingWhy human judgment, oversight, and ethics remain centralHow firms and legal departments can use the frameworkWhy smaller teams may benefit from AI training even moreHow law students can assess AI readiness in schools and employersLearn more about PLI’s AI-Ready Lawyer framework: [PLI AI-Ready Lawyer Framework] Hosted on Acast. See acast.com/privacy for more information.

What is an AI-native law firm? In this episode, Jen Leonard and Bridget McCormack are joined by John Nay, founder and CEO of Norm AI and Norm Law, for a conversation about agentic law, AI-native legal services, and what it means to build legal work around agents rather than copilots. John explains how legal and regulatory reasoning can be embedded into AI agents, allowing them to perform first-pass work, learn from prior matters, and create compounding value over time. The conversation also explores how Norm Law combines attorneys, legal engineers, software engineers, and AI engineers; why client-specific knowledge can become persistent; and how outcome-based pricing may change the business model of legal services. The episode also examines client trust, human supervision, experienced legal talent, and the Legal AGI Lab’s research into how AI agents may be evaluated, benchmarked, and governed by law. Learn more about the Legal AGI Lab: https://lab.norm.ai In this episode: What agentic law meansHow AI agents differ from copilotsWhat an AI-native law firm looks likeThe role of legal engineers and AI engineersOutcome-based pricing and client trustHuman supervision in AI-native legal workLegal AGI and the governance of AI agents Hosted on Acast. See acast.com/privacy for more information.

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 service providers to proactive strategic partners. The conversation explores why successful legal AI depends on data and context rather than simply deploying another chatbot, how AI systems can learn legal judgment over time, what lawyers should automate first, and why human oversight remains essential as agentic workflows become more common. Nick also shares why corporate legal departments are under increasing pressure as AI accelerates work across the business, and what that means for the future of legal teams. In this episode: Why in-house legal teams are adopting AI differently than law firmsBuilding AI-native legal infrastructureWhy legal AI is fundamentally a data and context problemHow AI can help legal teams become more proactiveWhat AI can—and can't—learn from lawyersUnderstanding agentic workflows and human oversightWhy implementation is the key to successful AI adoption Hosted on Acast. See acast.com/privacy for more information.

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 make change feel more accessible, and why collaboration, human-centered design, and practical experimentation matter in the AI era. The conversation also covers PLI’s AI competency framework, the value of business fables, the history of the Cravath system and the billable hour, how Jen used AI as a writing partner, and what the future of junior lawyer training might look like. Learn more about Unprecedented: Designing a Human-Centered Law Firm When Everything Is Changing: https://www.pli.edu/catalog/publications/treatise/unprecedented-designing-a-human-centered-law-firm-when-everything-is-changing/447974 In this episode: Why law firm change requires human buy-inHow storytelling can make transformation more usableWhy the current legal business model is not inevitableHow AI can act as a co-intelligence, not a shortcutWhat junior lawyer training might look like in the AI era Hosted on Acast. See acast.com/privacy for more information.

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 AI value, how AI-native firms may challenge incumbents, and why agentic AI creates new governance and security questions for legal organizations. In this episode: How legal tech adoption has shifted since ChatGPTWhy AI value is moving from efficiency to qualityWhat AI-native firms mean for incumbent law firmsHow law firms should evaluate legal tech startupsWhy agentic AI raises new governance risksWhat Nikki expects next for the legal tech marketKeywords: legal tech, legal technology, AI in law, legal AI, law firm strategy, Nikki Shaver, Legaltech Hub, agentic AI, AI-native firms, law firm innovation, legal innovation, GenAI, legal tech bubble, future of law Hosted on Acast. See acast.com/privacy for more information.

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 negotiate, accept terms, and complete transactions on behalf of people and businesses. In this episode: What Legal Context Protocol is designed to solveWhy agentic commerce creates new contract and ratification issuesHow legal terms can become discoverable, verifiable, and connected to transactionsWhy AI risk and legal-context risk should be separatedWhat general counsel and law firm partners should do now Hosted on Acast. See acast.com/privacy for more information.

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 law students used AI to synthesize legal materials, apply legal rules, and revise legal analysis—and why some results surprised even the researchers. In this episode: Why legal training may prepare lawyers to use AI wellWhat the University of Minnesota study tested about AI and legal reasoningWhy AI-assisted students performed better than expectedThe risks of using AI for revision under time pressureWhat law schools and law firms should take away from the research Hosted on Acast. See acast.com/privacy for more information.

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 AI strategies, and early signs of client-side disruption. In this episode: Am Law 100 power rankings and market concentrationThe rise of “apex predator” firmsAI strategy and firm-level competitionShifting client demand and pricing pressureThe future structure of Big Law Hosted on Acast. See acast.com/privacy for more information.

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 exponentially more value from AI than others, the growing importance of structuring legal knowledge into reusable protocols, and how contract data is becoming a strategic asset inside organizations. The conversation also examines shifting incentives, emerging career paths, and how legal education and training may need to evolve in response. Topics discussed include: AI agents and the shift from tools to systemsWhy some professionals get exponentially more value from AIContract lifecycle management and the rise of contract data as infrastructureThe changing role of lawyers from executors to system architectsLegal education, training models, and new career pathways Hosted on Acast. See acast.com/privacy for more information.

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, and whether existing legal frameworks can meaningfully apply to AI systems. They also explore practical AI use cases and key takeaways from Legalweek 2026, including rising pressure to demonstrate ROI, rapid enterprise adoption, and the shift toward more advanced systems. Topics discussed include: The facts and legal theories in Nippon Life v. OpenAIUnauthorized practice of law vs. product liability frameworksThe limits of regulating AI through court decisionsLegalweek 2026: ROI pressure and adoption trendsPractical AI workflows using Claude Co-Work Hosted on Acast. See acast.com/privacy for more information.