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46. How AI Is Changing Contract Law with Dave Hoffman
45:00||Ep. 46Artificial 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-ready” lawyer is harder than it sounds.Topics DiscussedUsing Claude to analyze law journals’ AI policies at scaleHow AI can support judges in interpreting contract languageThe changing value of transactional lawyers in an AI-driven worldHow legal education is adapting to rapid technological changeRethinking legal judgment, training, and professional value
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45. AI Recording Tools and Attorney-Client Privilege in the Age of AI
32:32||Ep. 45AI 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 risksState consent laws and the ethical limits of secret recordingNew York Bar Formal Opinion 2025-6 and deceptive practicesWhether recording changes how clients communicate with their lawyersThe risk of AI-generated summaries misinterpreting legal nuanceA risk-based framework for deciding when (and when not) to recordNew Wharton–Accenture research on how AI is reshaping job skills and compensationAI tools can improve legal work—but only when lawyers understand the boundaries that protect trust, competence, and confidentiality.
44. AI Agents and the Widening Divide in Legal with Zach Abramowitz
34:13||Ep. 44As 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 agentsWhy 2026 is about measuring ROI, not experimentationThe rise of AI-first firms and competitive pressure on traditional modelsVenture capital, private equity, and renewed conversations about external ownershipThe growing mindset divide within the professionAI is no longer a side experiment in legal. It is becoming embedded in strategy, pricing, and firm structure.
43. Claude Code, Vibe Coding, and Creative Lawyers at Work
34:11||Ep. 43What 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 workWhy creative associates are driving real changeVibe coding and lowering the barrier to innovationCultural shifts law firms need to support experimentationWhat this means for junior lawyers and legal training
42. Should Lawyers Trust AI? Inside Harvey and the Future of Legal Work
44:38||Ep. 42Can 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-loop systems shape real trust in legal AI. The conversation also dives into the future of the billable hour, lawyer training, and why AI is best understood as leverage—not labor replacement.In this episode:When lawyers will trust AI systemsHuman-in-the-loop governance and supervisionAI as law firm infrastructure, not just softwareWhy the billable hour isn’t disappearingTraining lawyers faster in an AI-first era
41. Private Equity and the Future of Law Firms: Investing in AI
31:19||Ep. 41Private 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 at stake.The conversation also examines emerging judicial approaches to AI disclosure and what they signal for competence, evidence, and governance as AI becomes foundational to legal practice.
40. Predictions for 2026 in AI and the Law
36:20||Ep. 40What 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 inside law firms. Along the way, they introduce ideas like AI legal twins, AI co-mediators, and opt-in court pilots for low-stakes disputes—and ask what leaders across the justice system should be planning for now.Topics Covered:How Gemini 3 and agentic AI systems move beyond simple chatbotsWhy private equity, MSOs, and ALSPs may “platformize” legal servicesThe new talent equation: from 1Ls to AI leaders in the C-suiteProvocative ideas like AI legal twins and AI co-mediatorsHow courts might experiment with opt-in AI pilots for low-stakes cases