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 systems
• Why some professionals get exponentially more value from AI
• Contract lifecycle management and the rise of contract data as infrastructure
• The changing role of lawyers from executors to system architects
• Legal education, training models, and new career pathways

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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. OpenAI
• Unauthorized practice of law vs. product liability frameworks
• The limits of regulating AI through court decisions
• Legalweek 2026: ROI pressure and adoption trends
• Practical AI workflows using Claude Co-Work

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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-ready” lawyer is harder than it sounds.

Topics Discussed

• Using Claude to analyze law journals’ AI policies at scale
• How AI can support judges in interpreting contract language
• The changing value of transactional lawyers in an AI-driven world
• How legal education is adapting to rapid technological change
• Rethinking legal judgment, training, and professional value

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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 2025-6 and deceptive practices
• Whether recording changes how clients communicate with their lawyers
• The risk of AI-generated summaries misinterpreting legal nuance
• A risk-based framework for deciding when (and when not) to record
• New Wharton–Accenture research on how AI is reshaping job skills and compensation

AI tools can improve legal work—but only when lawyers understand the boundaries that protect trust, competence, and confidentiality.

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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 experimentation
• The rise of AI-first firms and competitive pressure on traditional models
• Venture capital, private equity, and renewed conversations about external ownership
• The growing mindset divide within the profession

AI is no longer a side experiment in legal. It is becoming embedded in strategy, pricing, and firm structure.

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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 creative associates are driving real change
• Vibe coding and lowering the barrier to innovation
• Cultural shifts law firms need to support experimentation
• What this means for junior lawyers and legal training

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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-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 systems
• Human-in-the-loop governance and supervision
• AI as law firm infrastructure, not just software
• Why the billable hour isn’t disappearing
• Training lawyers faster in an AI-first era

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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 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.

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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 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 chatbots
• Why private equity, MSOs, and ALSPs may “platformize” legal services
• The new talent equation: from 1Ls to AI leaders in the C-suite
• Provocative ideas like AI legal twins and AI co-mediators
• How courts might experiment with opt-in AI pilots for low-stakes cases

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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 justice.” What emerges is a compelling vision for AI as a bridge—not a barrier—to legal help.

Topics:

• How AI is transforming access to justice

• Why the legal system leaves most people without help

• The creation of Depositron and LawAnswers AI

• “Second-tier justice” vs. real-world legal outcomes

• Moonshot visions for AI-enabled legal service delivery

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