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Pearls On, Gloves Off: The Legal Innovation Podcast
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Pearls On, Gloves Off: The Legal Innovation Podcast

Author: Mary O'Carroll

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Join Mary O'Carroll as she sits down with General Counsel, Chief Legal Officers, and industry pioneers to tackle the debates reshaping legal services and technology. Presented by Workday.
105 Episodes
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Mary sits down with Stanford Law's Adam Sterling and Irene Liu to unpack the school's new Legal Engineering Academy. They dig into what a legal engineer actually is, why the legal apprenticeship model has been broken for years, how AI-powered 'flight simulators' could compress a decade of experience into months, why AI may be pushing demand for young lawyers up rather than down, and what the legal talent ecosystem could look like ten years from now. This episode is presented by Workday. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts  
Mary sits down with Dr. Larry Richard, psychologist, former lawyer, and the foremost researcher on lawyer personality, for a return visit that goes even deeper than their first conversation. They dig into the seven personality traits that make lawyers uniquely wired for the law and uniquely challenged by everything else, why nine out of ten lawyers are thin-skinned, why empathy has dropped 50% in the last twelve years, what that means for legal leadership in an AI-driven world, and what the science actually says about how to change any of it. This episode is presented by Workday. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts  
Mary sits down with Ryan Daniels, Co-Founder and CEO of Crosby, for a rare look inside one of legal tech's most talked-about AI native law firms. They dig into why Ryan built a law firm instead of a legal tech company, how fixed fee pricing completely changes the unit economics of legal services, why Crosby lawyers are evaluated on speed not hours, how they're building a data moat from every contract they touch, and what it actually looks like when a law firm is designed from day one to hand work off to agents. This episode is presented by Workday. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts
Mary sits down with Darth Vaughn, Associate General Counsel and Managing Director of Policy and Legal Ops at Ford Motor Company, for a candid conversation about what it actually looks like when one of the world's largest legal departments stops waiting and starts building. They dig into why the billable hour model is structurally broken, what Ford actually expects from its outside counsel, why AI native firms still have a trust problem, and what the legal department of the future really needs to look like - from someone already living it. This episode is presented by Workday. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts
Mary sits down with Eric Greenberg, EVP, Chief Legal Officer, and Corporate Secretary at Cox Media Group, for a milestone 100th episode conversation about what it actually takes to lead a legal department through transformation. They dig into why AI governance is really an anthropology problem, why buying software is the beginning not the end, the future of big law and outside counsel relationships, and why the most important leadership skill right now is making it okay to be wrong. This episode is presented by Workday. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts
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