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48. Jason Barnwell on AI Agents, Contract Lifecycle Management, and the Future of Legal Work
36:27||Ep. 48Artificial 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
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47. Did AI Just Practice Law? The OpenAI Lawsuit + Legalweek 2026
34:24||Ep. 47Artificial 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-Work46. 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 value45. 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 training42. 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