In this episode of AI Sidebar, Irene Liu talks with Anna Gorodetsky, a partner at Major, Lindsey & Africa who oversees in-house counsel recruiting, about what law firms and legal departments are looking for in the age of AI. Gorodetsky shares what she is seeing in the market, from new AI innovation roles at law firms to the pressure on in-house teams to do more with technology. Irene and Anna also discuss the practical AI experience employers increasingly expect, what practicing lawyers and law students can do to stand out, and why judgment, communication, trust, and business context remain central to great lawyering.

Link List:

Learn more about the Stanford Law School AI Initiative

Irene Liu, Executive Director of the Stanford Law School AI Initiative

Connect with Anna Gorodetsky

Chapters:

(00:00:00) Introduction

(00:01:03) The Legal Hiring Market in the Age of AI

(00:03:29) Layoffs, Freezes, and Legal Team Restructuring

(00:05:31) Pressure on In-House Teams

(00:07:30) The Rise of the “Lawyer Plus” Profile

(00:08:49) AI Skills and Compensation

(00:11:28) What Have You Built With AI?

(00:14:22) AI in the Interview Process

(00:16:27) How Lawyers Can Stay Competitive

(00:19:48) New AI Roles at Law Firms

(00:21:43) Where Firms Are Finding AI Talent

(00:24:30) What AI Innovation Leaders Need to Succeed

(00:26:59) Preparing Law Students for an AI-Driven Market

(00:29:26) What Makes Top Candidates Stand Out

(00:32:20) How Candidates Can Become More Marketable

(00:34:53) The Future of Legal Hiring

(00:38:08) Conclusion

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In this episode of AI Sidebar, Irene Liu talks with Heather Meeker, an internationally recognized open source software licensing expert, partner at TechLaw Partners, co-founder of Chinstrap Community, and author of Open Source for Business. Meeker explains why open source AI is harder to define than open source software, how open weights differ from truly open models, and why that distinction matters for lawyers advising companies on how these tools can be used. Irene and Heather also explore what legal and business leaders should know as open weight models enter organizations, from licensing and governance to security, transparency, and public trust.

Learn more about the Stanford Law School AI Initiative

Irene Liu, Executive Director of the Stanford Law School AI Initiative

Connect with Heather Meeker

Pre Order your copy of Open Source for Babies

Chapters:

(00:00:00) Introduction

(00:01:14) What Does Open Source AI Mean?

(00:05:52) Open Source vs. Open Weights

(00:07:38) Why Open Source AI Is Having Its Moment

(00:09:44) Are Any AI Models Truly Open Source?

(00:10:25) Chinese Models and the Competitive Landscape

(00:11:49) Governing Open Weights in Organizations

(00:14:08) Compliance Tools and Shadow AI

(00:15:25) How Legal Teams Can Help, Not Block

(00:17:06) Security and Governance for Chinese Models

(00:19:00) Why Legal and IT Need to Work Together

(00:20:24) Sharing AI Best Practices

(00:21:21) The Open Weights Policy Debate

(00:23:15) Are Open Models Riskier?

(00:25:14) Transparency, Safety, and Linus’s Law

(00:27:27) The Regulatory Landscape

(00:30:35) Open Source for Babies

(00:33:11) How Lawyers Can Keep Up

(00:37:21) Conclusion

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In this episode of AI Sidebar, Irene Liu talks with Ryan Daniels, co-founder and CEO of Crosby AI and a Stanford Law School alum, about what he’s learned building an AI-native law firm focused on commercial contracts. Daniels explains what “AI-native” means in practice, how Crosby differs from both a traditional law firm and a legal tech company, and why it remains, at its core, a law firm. Irene and Ryan also explore how AI can take on repetitive legal work, reshape the law firm business model, and make this an especially exciting time for lawyers who want to innovate.

Learn more about the Stanford Law School AI Initiative

Irene Liu, Executive Director of the Stanford Law School AI Initiative

Connect with Ryan Daniels

Learn more about Crosby

Chapters:

(00:00:00) Introduction

(00:00:53) What Is an AI-Native Law Firm?

(00:02:39) Why Build a Law Firm Instead of Legal Tech?

(00:03:33) Why Commercial Contracts?

(00:04:54) Pricing by Deal, Not by Hour

(00:06:34) Measuring Human Review Time

(00:07:46) Designing AI Around Lawyers

(00:10:44) Keeping Lawyers in Control

(00:12:22) Building Empathy Between Engineers and Lawyers

(00:14:53) Lawyers, Engineers, and the Identity of an AI-Native Firm

(00:16:31) Finding Lawyers for a New Model

(00:18:15) Why Great Lawyers May Become More Valuable

(00:19:50) Why Clients Try Crosby

(00:20:53) The Future of AI-Native Law Firms

(00:21:37) Defining Quality in Legal AI

(00:22:30) Why This Is an Exciting Time to Build

(00:23:18) Advice for Lawyers and Law Students

(00:25:05) Conclusion

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Drawing on his experience at Slack and Anthropic, Pike offers a firsthand look at what product counseling requires when legal teams are advising not just on AI, but alongside it. Irene and Mark explore how lawyers can build trust with product and engineering teams, why technical curiosity matters, and how tools like Claude for Legal are reshaping the way legal guidance is created, delivered, and scaled. The conversation also points to a broader question for the profession: whether AI will reduce legal work or expand the universe of legal questions that teams are able to see and address.

Learn more about the Stanford Law School AI Initiative

Irene Liu, Executive Director of the Stanford Law School AI Initiative

Connect with Mark Pike

Explore Claude for Legal on GitHub

Watch Mark's Presentation at Stanford

Chapters:

(00:00:00) Introduction

(00:01:15) How Product Counseling Has Changed

(00:03:17) From Pat Signals to AI Agents

(00:04:38) Product Counseling in the Agentic Era

(00:06:41) The Product Lawyer as Miniature GC

(00:08:09) Getting Closer to the Work

(00:09:39) What Happens When Everyone Is a Builder?

(00:12:51) Guardrails, Automation, and Human Judgment

(00:15:13) Training Product Teams With Better Tools

(00:16:38) Making Legal Training Memorable

(00:19:05) Knowing When to Call in Experts

(00:20:42) Using AI to Understand New Legal Issues

(00:22:23) Working With Outside Counsel in the AI Era

(00:23:27) Technical Fluency for Product Lawyers

(00:25:13) Learning by Building

(00:29:16) Managing AI Agents

(00:31:53) Will AI Create More Legal Work?

(00:33:43) What Comes Next for Claude for Legal

(00:35:06) Conclusion

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In this episode of AI Sidebar, Irene Liu talks with Stanford Law Professor Julian Nyarko, faculty director of liftlab and co-director of Stanford Law’s AI Initiative, about his recent study examining how legal experts evaluate AI-generated work. Nyarko explains what the study reveals, why its findings matter for both legal education and practice, and how rigorous research can help the profession determine when AI performs well, when it falls short, and when it should be trusted. He also discusses how liftlab is evaluating AI across legal services, research, and education, including when AI tutors can support student learning and when they may get in the way.

Together, they explore how this research is shaping Stanford Law’s approach to AI in the classroom, from tutoring tools to simulated negotiations, and what it may mean for the future of legal expertise and education.

Learn more about the Stanford Law School AI Initiative

Irene Liu, Executive Director of the Stanford Law School AI Initiative

Julian Nyarko Stanford Profile

Learn more about liftlab

“Law Professors Prefer AI Over Peer Answers”

Chapters:

(00:00:00) Introduction

(00:00:55) What Is liftlab?

(00:02:41) The Four Core Pillars of liftlab

(00:07:39) The Art of Contracts

(00:10:25) How liftlab uses AI

(00:13:54) The Study: “Law Professors Prefer AI Over Peer Answers”

(00:18:56) AI Tutors in Legal Education

(00:21:52) Potential Applications of the Findings

(00:23:02) Study Modifications

(00:24:43) Classroom Adaptation of the Study

(00:28:33) Underrated & Overhyped Uses of AI in Law

(00:33:15) Judgment, Lawyers, and the Future of AI

(00:34:48) Conclusion

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In this episode, host Irene Liu sits down with Mary O’Carroll, CEO of LegalEng Consulting Group and a longtime leader in legal operations and legal technology, to discuss legal ‘rightsourcing’ in the age of AI. Drawing on her experience across Google, Ironclad, law firms, legal tech companies, and consulting, O’Carroll explains why buying AI tools is only the beginning, and why the real opportunity lies in reimagining legal work itself. Together, they explore the shift from legal operations to legal engineering, the growing demand for legal solutions engineers and forward deployed engineers, and the talent gap facing in-house teams, law firms, and AI legal tech companies as they rethink how legal services are delivered.

Learn more about the Stanford Law School AI Initiative

Irene Liu, Executive Director of the Stanford Law School AI Initiative

Connect with Mary O'Carroll

LegalEng Consulting Group

Chapters:

(00:00:00) Introduction

(00:00:59) The Evolution of Legal Operations

(00:03:12) Why Buying AI Tools Is Only the Beginning

(00:04:03) From Acceleration to Reimagining Work

(00:06:18) Reengineering Legal Workflows

(00:09:42) What Legal Engineering Really Means

(00:12:20) Where Legal Engineers Fit

(00:13:52) The Rise of Forward Deployed Engineers

(00:15:14) The Legal Solutions Engineer

(00:17:00) Preparing the Next Generation of Legal Talent

(00:18:35) Changing How Large Organizations Work

(00:23:04) Practical First Steps for Legal Teams

(00:26:17) Why Alignment Comes Before Automation

(00:28:10) How Law Firms Should Invest in AI

(00:32:45) Where to Invest First

(00:36:16) Conclusion

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In this episode of AI Sidebar, host Irene Liu sits down with April Miller Boise, former executive vice president and chief legal officer of Intel, to discuss how legal leaders can guide their organizations through both AI adoption and broader corporate transformation. Drawing on her experience leading Intel’s legal and corporate functions through a period of major change, Boise explains why CLOs must set the tone from the top, align AI strategy with business priorities, and remap legal work rather than simply layering new tools onto old processes. Together, they explore practical techniques Miller Boise used for leading transformation, from benchmarking legal tech and running AI sprints to training teams, rethinking law firm partnerships, and building the legal department of the future as generative and agentic AI reshape in-house practice.

Learn more about the Stanford Law School AI Initiative

Irene Liu, Executive Director of the Stanford Law School AI Initiative

April Miller Boise, Former Executive Vice President & CLO, Intel

Chapters:

(00:00:00) Introduction

(00:01:06) Leading Intel Through Transformation

(00:03:05) Aligning Legal Teams With Business Strategy

(00:05:20) Strategy on a Page

(00:06:44) Moving From AI Awareness to Experimentation

(00:09:17) Why CLOs Must Lead Strategy Change

(00:12:52) Benchmarking AI Across Legal Departments

(00:16:14) Building an AI Task Force

(00:18:45) Running AI Sprints

(00:21:51) Encouraging Training in AI

(00:24:21) Key Lessons From the AI Survey

(00:25:46) Remapping Legal Work

(00:28:09) The Legal Department of the Future

(00:32:12) Rethinking Law Firm Partnerships

(00:36:18) Advice for New CLOs

(00:39:25) Conclusion

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In the debut episode of AI Sidebar, host Irene Liu sits down with Stanford Law School Dean George Triantis, who lays out Stanford Law’s overall approach to AI: prepare students to use the technology fluently and responsibly, preserve the human judgment at the heart of lawyering, and help legal institutions adapt to a rapidly changing world. From the launch of Stanford Law’s AI Initiative to the rise of AI agents, legal tech tools, and AI-native law firms, Dean Triantis explains why adaptability, ethics, and trust will remain central, even as the tools of the trade change rapidly. Together, they discuss how Stanford Law is preparing students for an AI-enabled profession, why “human in the loop” thinking is essential, and what legal education must get right as AI transforms the practice and purpose of law.

Learn more about the Stanford Law School AI Initiative

George Triantis, Richard E. Lang Professor of Law and Dean of Stanford Law School

Irene Liu, Executive Director of the Stanford Law School AI Initiative

Chapters:

(00:01:10) A Career in Legal Education

(00:04:14) Why AI Matters to Law Schools

(00:06:26) Launching Stanford Law’s AI Initiative

(00:08:45) Preparing Students for an AI-Enabled Profession

(00:14:04) From Westlaw to AI Agents

(00:16:49) Preserving Foundational Legal Skills

(00:20:03) What Will Distinguish Excellent Lawyers

(00:23:02) AI in the Classroom

(00:27:38) What Law Firms and Alumni Are Saying

(00:32:26) Looking Five Years Ahead

(00:34:33) The Future of the AI Initiative

(00:37:38) Conclusion

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From the heart of the Bay Area, where AI is being built, debated, and put to the test, the show cuts through the noise to unpack the biggest developments shaping law, business, society, and all of us. Each episode asks the questions that matter: Who is accountable when AI calls the shots, how should we regulate powerful new tools, and what skills will tomorrow’s lawyers need? AI Sidebar is a clear, timely guide to how AI is reshaping the law and how the law may shape the future of AI.

Join us every other Monday for AI Sidebar, from Stanford Law School, available on all listening platforms. Subscribe, share, and stay informed.

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