Advertise on podcast: Pearls On, Gloves Off: The Legal Innovation Podcast

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

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

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

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

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

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

In today's episode, Mary sits down with Aine Lyons, Senior Vice President & Deputy General Counsel and Chief Strategy Officer at Workday, to talk about what it actually takes to build a modern legal department. They cover why Aine deliberately designed Workday's function without a traditional legal ops silo, what it means to reskill every lawyer in the department, and why guardrails and governance matter just as much as the agents you're building on top of them. This episode is presented by Workday ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Brightflag ~~~ Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

In today's episode, Mary sits down with Michael Pierson and Joel Ferdinand, Co-Chairmen of Pierson Ferdinand, and Christina Wojcik, their Chief Innovation Officer. Together, they break down what it actually takes to build the law firm of the future and why buying AI tools without rethinking your structure, culture, and compensation model is the wrong place to start. This episode is presented by Workday ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Brightflag ~~~ Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

In today's episode, Mary sits down with Winston Weinberg, CEO and Co-Founder of Harvey.ai, to talk about what it actually takes to transform legal - and why buying AI tools without rethinking how your entire organization operates is the wrong place to start. This episode is presented by Workday. ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Brightflag ~~~ Support the show! Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

In today's episode, Mary sits down with Virginia Briggs, CEO and Managing Partner of MinterEllison, to talk about what real AI transformation actually looks like inside a law firm. This episode is presented by Workday. ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Kodex Brightflag ~~~ Support the show! Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

When Ross McNairn realized his legal career meant reviewing 15,000 documents by hand, he didn't just question the system - he rewrote it. Literally. In this episode, Mary sits down with the Wordsmith ai founder to unpack what happens when a former lawyer turned engineer takes on legal's biggest inefficiencies and why AI is about to redraw the boundaries between in-house teams and law firms. From exploding startup valuations to the rise of "shadow legal," Ross brings a builder's lens to a profession in flux. The result is a candid, sometimes uncomfortable look at where legal work is actually headed, and who stands to win. This episode of Pearls On, Gloves Off is powered by Workday. Learn more at workday.com. In this episode: The Breaking Point: Ross shares the exact moment he realized private practice incentives reward inefficiency, and why that pushed him to build instead of bill. AI's Real Impact on Legal Spend: Why in-house teams are poised to cut 70–80% of external counsel costs, and why no GC is asking for more law firm dependency. The Two-Sided Market Problem: Can one product truly serve both law firms and in-house teams when their incentives are fundamentally opposed? The Founder Reality Check: Behind the hype of legal AI startups - what building a company actually feels like, and why most won't survive the next wave. The Rise of Legal Engineering: The emerging role that blends law, systems thinking, and AI - and why it may become the most in-demand job in legal. Who Wins Next: Ross's prediction that up to 80% of current legal tech players won't survive the coming platform shift. If you're trying to make sense of legal AI beyond the hype, this conversation delivers a clear-eyed view of what's changing, what's breaking, and what's being built next. Thank you to our sponsors for making this show possible. Wordsmith.ai Kodex Brightflag ~~~ Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts