Pearls On, Gloves Off: The Legal Innovation Podcast

Hosted by Mary O'Carroll

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106

Latest episode

Oct 2026

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About the show

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 Practicing Law Institute.

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60 recent

October 13, 2026Episode 1051 hr 4 min

#105 - Disrupt Yourself First: How Redgrave Is Rebuilding the Law Firm Model

Mary sits down with Erica Zolner, Britney Colton, and Ray Mangum of Redgrave LLP, an information law firm that runs nothing like a traditional firm. They dig into what happens when lawyers and technologists work side by side, how AI turned 600,000 contract PDFs into a risk picture in five days, why disrupting yourself beats waiting to be disrupted, why clients still hold on to the billable hour, and how real-time feedback shapes how the firm rewards its people. This episode is presented by PLI. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

September 29, 2026Episode 10455 min

#104 - Flight Simulators for Lawyers: The Rise of the Legal Engineer and How the Profession Learns

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

September 15, 2026Episode 1031 hr 15 min

#103 - The Lawyer Personality Unpacked: What the Data Says After 32 Years of Research

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

September 1, 2026Episode 10257 min

#102 - Inside Crosby: The AI Law Firm Rethinking How Legal Work Gets Done

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

August 18, 2026Episode 10151 min

#101 - Ford's Warning Shot: Adapt or Get Left Behind

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

August 4, 2026Episode 10058 min

#100 - The Future of Legal Is Already Here - A Conversation with CLO Eric Greenberg

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

July 21, 2026Episode 9954 min

#99 - Who Is Sandstone? Inside Legal Tech's Most Talked-About Company

Mary sits down with Nick Fleisher, Co-Founder and CEO of Sandstone, to pull back the curtain on legal tech's fastest-rising company. They dig into why great software still matters in the age of AI, how Sandstone is solving the permissions and context problem that's plagued in-house legal for years, why law firms will never out-build tech companies, and how an AI-native team is redefining what it means to build lean. This episode is presented by Workday. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

July 7, 2026Episode 9851 min

#98 - Anna Richards

Mary sits down with Anna Richards, Head of Community at Brightflag, to catch up on what's actually happening on the ground in legal ops right now. They dig into the shifting skill sets legal ops leaders need, how to think about building a tech stack from scratch, and why the job keeps getting harder even as expectations keep climbing. This episode is presented by Workday. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts ~~~ Thank you to our sponsors for making this show possible. Kodex

June 23, 2026Episode 9752 min

#97 - The Senior Talent Problem Nobody Wants to Talk About

In today's episode, Mary sits down with James O'Dowd, CEO and founder of Patrick Morgan, to explore what legal can learn from the PE and AI disruption already reshaping accounting and consulting. James breaks down why governance is the real unlock private equity brings, how compensation models are shifting away from legacy profit-sharing, and why cultural buy-in ultimately determines whether any of it sticks. On AI, James unpacks the concept of "talent debt" and closes with a bold prediction: a major technology player acquiring a large professional services firm may not be as far off as it sounds. This episode is presented by Workday. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts ~~~ Thank you to our sponsors for making this show possible. Kodex

June 9, 2026Episode 9653 min

#96 - Curating AI Tools for a Global Law Firm

In today's episode, Mary sits down with Ilona Logvinova, Chief AI Officer at HSF Kramer, to talk about what it actually takes to turn a global law firm into an AI native organization. They cover why the Chief AI Officer title means something different from innovation, what it takes to build a forward deployed legal engineering function, and why the real edge isn't buying technology - it's the people and incentives behind it. This episode is presented by Workday ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Kodex ~~~ Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts