AI and the Future of Law

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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