Mike Gerstenzang (Cleary Gottlieb): AI from the Inside

CJ Mahoney (Meta): Inside Counsel at Scale

In this episode of New Law Order, Joel Cohen and Yale Law Professor John Morley speak with CJ Mahoney, Chief Legal Officer of Meta, about one of the hardest legal questions facing modern technology companies: when a product becomes deeply woven into daily life, how should the law think about harm, responsibility, and regulation? Drawing on a career that has taken him from Williams & Connolly to the Office of the U.S. Trade Representative, Microsoft, and now Meta, Mahoney offers an unusually candid look at what it means to serve as the top lawyer inside a company operating at the center of law, politics, and technological change. A major focus of the conversation is the growing wave of litigation against Meta alleging that its products are addictive and harmful, particularly for younger users. Mahoney explains how Meta sees those cases, why he believes the underlying social and mental-health issues are more complex than the lawsuits suggest, and why he is skeptical that litigation is the best tool for addressing those concerns. The episode explores the tension between genuine public anxiety about screen time, adolescent well-being, and platform design, on the one hand, and the difficulty of translating those concerns into coherent legal standards on the other. The discussion also turns to the broader challenge of regulating a company like Meta. Mahoney reflects on defending Meta’s acquisitions of Instagram and WhatsApp, the problem of assigning legal responsibility in fast-moving technological environments, and the way major platforms increasingly face pressure to answer for social problems that may be real, but are not easily reducible to a single product or defendant. It is a conversation not just about Meta, but about the limits of courts, the ambitions of regulators, and the strain placed on legal doctrine when technology changes faster than consensus can form around it. Finally, the episode turns to AI and the legal profession. Mahoney discusses how Meta’s legal department is already using AI for summarization, drafting, spend management, and workflow support, and why he sees the next phase not as isolated AI tools, but as deeper integration into business processes. He also offers a clear-eyed view of what that means for lawyers and law firms: more pressure on routine work, greater importance for judgment and strategy, and a world in which knowing how to use AI may become part of baseline professional competence. Guest: CJ Mahoney is the Chief Legal Officer of Meta. Previously, he served in senior legal roles at Microsoft and as Deputy United States Trade Representative, where he played a central role in the renegotiation of NAFTA into the USMCA. Earlier in his career, he was a partner at Williams & Connolly, one of the nation’s leading litigation firms. For more conversations with the figures reshaping the legal business, subscribe to New Law Order. For a CLE-eligible version of this interview and more legal analysis, visit www.talksonlaw.com. For questions or comments, email newlaworder@talksonlaw.com.

Richard Sander (UCLA Law): A Mismatch Critique of Affirmative Action

Richard Sander, UCLA law professor and economist, has spent decades advancing one of the most controversial arguments in legal education: that large racial preferences in law school admissions may frequently harm the students they are intended to help. In this episode of New Law Order, Joel Cohen and Yale Law Professor John Morley speak with Sander about affirmative action, the Supreme Court’s decision in Students for Fair Admissions, and what new data may reveal about the future of law school admissions. Sander explains his “mismatch” hypothesis: the claim that students admitted with very large academic preferences may be more likely to struggle academically, land at the bottom of the class, and face lower odds of passing the bar than if they had attended a school where their entering credentials were closer to the median. The discussion is direct, data-heavy, and often uncomfortable, touching on race, merit, institutional secrecy, bar passage, and the incentives that shape elite legal education. Sander also examines what changed after SFFA. He argues that the first post-SFFA admissions cycle produced one of the most dramatic shifts in elite law school admissions in decades, with some schools appearing to reduce racial preferences substantially while others found ways to preserve diversity through different admissions strategies. Joel and John press Sander on the strength of the evidence, the limits of the mismatch theory, and whether the legal academy has been willing to test its own assumptions. The episode then turns from law schools to law firms. If elite employers continue to hire for diversity while drawing heavily from credential-driven pipelines, what obligations do they have to train, support, and retain the lawyers they recruit? Sander argues that real affirmative action cannot stop at admission or hiring; it must include institutional investment after the offer is made. Guest: Richard Sander is a professor at UCLA School of Law and a PhD economist whose work focuses on law, inequality, housing, and affirmative action. He is one of the leading academic critics of racial preferences in higher education and was cited by the Supreme Court in Students for Fair Admissions v. Harvard. For more conversations with the figures reshaping the legal business, subscribe to New Law Order. For a CLE-eligible version of this interview and more legal analysis, visit www.talksonlaw.com [http://www.talksonlaw.com]. For questions or comments, email newlaworder@talksonlaw.com.

Mike Gerstenzang (Cleary Gottlieb): AI from the Inside

Michael A. Gerstenzang, the longtime managing partner and now senior partner of Cleary Gottlieb Steen & Hamilton, explains how he positioned one of the world's most established law firms to lead in AI adoption — not by outsourcing innovation, but by building it from the inside. The conversation traces a series of structural bets that began before generative AI entered the mainstream, starting with ClearyX, a wholly owned technology subsidiary launched in 2021 to reinvent M&A due diligence. Gerstenzang describes the venture's founding provocation — imagine the business that puts Cleary Gottlieb out of business, and build it — and how A/B testing against traditional associate-led diligence demonstrated equal or superior quality at roughly half the cost. The discussion turns to the firm's acquisition of Springbok AI, a legal technology development company whose team now forms Cleary's internal AI acceleration unit, and what that acqui-hire reveals about a deeper challenge confronting every major firm: how to attract and retain elite technologists who would otherwise choose OpenAI or Anthropic over a law firm. Gerstenzang argues that the profession's relationship to technology must shift from infrastructure maintenance to client-facing partnership, and that partners need not master AI themselves but must stop building walls and start supporting those who build windmills. The episode examines the billable hour's structural misalignment with AI-driven efficiency, the emergence of fixed-fee and subscription billing models, and why firms that resist technological adoption will not preserve their margins but simply lose the work to competitors who embrace it. Throughout, Gerstenzang is unsparing about the limitations of the traditional law firm model but remains deeply optimistic about the future of lawyering — practiced increasingly alongside, and powered by, sophisticated technology. For more conversations with the figures reshaping the legal business, subscribe to New Law Order. For a CLE-eligible version of this interview and more legal analysis, visit www.talksonlaw.com [%5C]. For questions or comments, email newlaworder@talksonlaw.com.  Michael A. Gerstenzang, the longtime managing partner and now senior partner of Cleary Gottlieb Steen & Hamilton, explains how he positioned on

Judge Paul Grimm: Deep Fakes in the Courtroom

This week, we’re sharing a timely episode from a related TalksOnLaw podcast, AI Lawyer. In this episode, host Joel Cohen is joined by Judge Paul Grimm for a conversation about one of the most unsettling problems facing the legal system: what happens when audio, video, and other forms of evidence can be generated, manipulated, or challenged by artificial intelligence? Judge Grimm explains how AI is already affecting the justice system long before trial, from predictive policing and facial recognition to risk-assessment tools like COMPAS. The episode explores how these systems can influence investigations, charging decisions, sentencing, and the presentation of evidence in court, often with serious consequences and imperfect transparency. The conversation then turns to deepfakes and synthetic evidence: the growing reality that highly convincing fake audio and video can distort proceedings, while the mere existence of deepfakes makes it easier to deny real evidence too. Joel and Judge Grimm unpack the evidentiary challenges this creates for judges, lawyers, and juries, including questions of authentication, reliability, prejudice, and whether existing evidence rules are equipped to handle these technologies. At bottom, this is a conversation about trust, proof, and the future of adjudication. As courts confront black-box systems and increasingly sophisticated digital deception, Judge Grimm offers a sober but practical look at how judges can use existing legal frameworks while the law struggles to catch up. Guest: Judge Paul Grimm is a former federal district court judge and a professor of law at Duke Law School who has written extensively on evidence, technology, and artificial intelligence. For more conversations with top thinkers at the intersection of law and technology, subscribe to New Law Order. For more legal analysis and CLE-eligible content, visit TalksOnLaw. To listen to more episodes of AI Lawyer [https://podcasts.apple.com/us/podcast/ai-lawyer/id1761909412], search for AI Lawyer wherever you get your podcasts.

Jason Boehmig (Ironclad): The Rise of the Legal Technologist

Artificial intelligence is beginning to change not just how lawyers work, but what parts of the job remain distinctly human. In this episode of New Law Order, we speak with Jason Boehmig, founder and CEO of Ironclad, about how AI and legal technology are reshaping the structure of the legal profession. Boehmig explains to hosts Joel and John that software is increasingly taking over the mechanical work of law—document manipulation, contract routing, approvals, and data extraction—freeing lawyers to focus on judgment, strategy, and legal reasoning. While this promises massive benifits to lawyers and their clients, the shift raises uncomfortable questions: if AI tools can dramatically increase speed and accuracy, at what point does failing to use them begin to look like malpractice? And as contracts and legal documents become structured datasets, where is the line between practicing law and analyzing legal data? Drawing on his experience building technology for legal teams, Boehmig explains why many important innovations in legal tech have emerged outside traditional law firms. When legal work is decoupled from the billable hour—as it is inside corporate legal departments—the incentives shift toward efficiency, automation, and system design. That environment has become a laboratory for new ways of organizing legal work. The conversation also explores what these changes may mean for the profession itself. Boehmig predicts fewer traditional junior lawyers performing repetitive work and the emergence of new roles—“legal engineers,” technologists, and data specialists—working alongside attorneys. Much like finance evolved from human traders to a hybrid world of traders and quantitative engineers, the legal industry may be heading toward a similar transformation. Guest: Jason Boehmig is the founder and CEO of Ironclad, an AI contracting company used by legal teams at many of the world’s leading technology companies. A former lawyer at Fenwick, he founded Ironclad after teaching himself to code and becoming convinced that software could fundamentally reshape the way legal work is performed. For more conversations with the figures reshaping the legal business, subscribe to New Law Order. For a CLE-eligible version of this interview and more legal analysis, visit www.talksonlaw.com [%5C]. For questions or comments, email newlaworder@talksonlaw.com.