New Law Order

Big Law has spent decades and a fortune on diversity, and the numbers barely moved at the partnership level. The usual explanation is that somewhere in the building (or somewhere in your head) there's racism and misogyny. David Wilkins, Harvard Law professor and possibly the most important scholar on the legal profession, has a less satisfying answer: you don't need bigots to get this result. You just need busy partners.In this conversation, Wilkins joins Joel and John to explain how a firm full of well-meaning people still produces lopsided results. Partner time is scarce. Partners hand it out on almost no information, so they bet on associates who look like the last associate who made it, and hesitate over the profiles they've watched walk out the door. That partner isn't a villain, Wilkins says. He's just "a person in a competitive market."Wilkins also takes apart Big Law's favorite metaphor — the "tournament" where associates compete and the best rise to partner. Partners aren't neutral umpires with time for all. They're busy people rationing training, and the associate with a sponsor or a feel for the unwritten rules draws the good work while an equally capable one drafts the same motion for the ninth time. Money runs through all of it: who gets to Harvard, who graduates without loans, who can survive a lean year. Wilkins describes a loop where family wealth becomes educational capital, then opportunity, then wealth again.Then there's the post-SFFA landscape, where firms have quietly killed their fellowships and stopped saying the word "diversity" out loud. (Longtime listeners will recall our earlier guest Richard Sander, Episode 10, made the case for the decision.) Wilkins is less impressed with what firms have done since. His point is that the Court reached admissions, not hiring, and much of the retreat traces to political pressure that goes well beyond anything the Court held. The demographics didn't change. Neither did the structural problem.The encouraging part, in Wilkins's telling: a firm that fixes how it hands out training, sponsorship, and real work doesn't just get more diverse. It gets better at finding the talent it's currently wasting.Guest: David B. Wilkins is Vice Dean for Global Initiatives on the Legal Profession and Faculty Director of the Center on the Legal Profession at Harvard Law School. He has written more than 80 articles on how lawyers actually build careers, co-authored The Making of Lawyers' Careers (the twenty-year After the JD study), and his working motto is "great lawyers are made, not born."For more conversations with the titans changing the legal business, subscribe to New Law Order. For a lawyer CLE version of this interview and other legal insights, visit www.talksonlaw.com. For questions or comments about the show email us at [email protected].

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 [email protected].

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. For questions or comments, email [email protected].

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. For questions or comments, email [email protected]. Michael A. Gerstenzang, the longtime managing partner and now senior partner of Cleary Gottlieb Steen & Hamilton, explains how he positioned on

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, search for AI Lawyer wherever you get your podcasts.