

Pearls On, Gloves Off
Mary O'Carroll
Smooth operations keep businesses afloat – but what makes them successful? "Pearls On, Gloves Off" is a new podcast where Legal Ops legend Mary O'Carroll and a motley crew of guests share their insider knowledge from running high-performing businesses. Join us for insightful conversations with some of today's most respected leaders and luminaries.
Episodes
Mentioned books

Dec 23, 2025 • 44min
#84 - Resetting the Relationship with Outside Counsel
Mary O'Carroll welcomes Stephanie Hamon (Global Head of Legal External Engagement, HSBC) to explore how in‑house legal teams are rethinking their relationships with law firms, vendors, and the broader legal ecosystem. With experience spanning Barclays, Norton Rose Fulbright, and now HSBC, Stephanie brings a uniquely global and pragmatic perspective to legal transformation - from process redesign to AI's impact on delivery models. In this episode: The new panel model: Stephanie explains how HSBC is moving beyond transactional vendor management toward deeper, collaborative partnerships with firms and providers. Legal ops as a mindset: It's not just a function. Stephanie shares why ops is about how you think, not just who you hire. People, process, then tech: Before chasing the next tool, Stephanie urges legal teams to address foundational issues in process and data. Why consulting helps (at first): For legal departments overwhelmed by where to start, Stephanie outlines how consultants can build clarity and roadmaps before you hire in‑house. The death of the billable hour?: As AI and internal tooling reshape what gets sent outside, pricing models need to shift from time to value. Joint talent development: Stephanie makes a strong case for collaborative training between firms, clients, and academia to fix the broken legal talent pipeline. Three reasons we go external: Capacity, capability, and strategic insurance - and why each is evolving. Law firms under pressure: How client-side innovation is forcing firms to rethink delivery, pricing, and partnership structures. If you've been trying to future‑proof your outside counsel strategy - or are wondering how AI is reshaping legal budgets, this conversation is a clear-eyed, practical guide to what's next. Follow Mary on LinkedIn Rate and review on Apple Podcasts

Dec 9, 2025 • 40min
#83 - Recruiting Gen Z Lawyers in a Broken System
Genevieve Riccardelli and Jennifer Soltau, legal recruiters at Goodwin, discuss the evolving landscape of law-firm hiring. They reveal that traditional recruiting practices are fracturing, with firms locking in talent years ahead of actual needs. A growing number of Gen Z candidates prioritize in-house roles and diverse career paths, reshaping firm expectations. The guests emphasize the necessity for firms to engage with candidates and design programs that align with their desires, plus the increasing importance of tech fluency in future hires.

11 snips
Nov 25, 2025 • 49min
#82 - Deloitte Prices for Outcomes. Law Firms Will Too.
Ben Campbell, General Counsel at Deloitte and former DOJ prosecutor, shares insights on transforming law firms. He discusses the shift from traditional hourly billing to outcome-based pricing, aligning incentives with clients. Governance at Deloitte features a unique partnership model that enhances collaboration. Ben emphasizes the importance of flexible career paths to retain talent and addresses the impact of AI on the legal profession, suggesting law firms adopt more dynamic structures and modern pricing models before falling behind.

6 snips
Nov 11, 2025 • 41min
#81 - The New Structure of AI Powered Law Firms
David Duncan, a seasoned author and advisor on disruptive innovation, and Tyler Anderson, CEO of Disruptive Edge specializing in AI strategy, dive into how AI is radically transforming law and consulting firms. They discuss the shift from traditional staffing models to an 'obelisk' structure and the need for firms to adopt AI at their core rather than as an add-on. The duo also tackles the challenges of pricing, talent development, and the advantages nimble AI-first firms have over legacy systems, urging a proactive opportunity mindset towards AI.

11 snips
Oct 28, 2025 • 41min
#80 - Harvey AI's GC: Lawyers Are 20x More Efficient... Now What?
In this discussion, John LaBarre, General Counsel at Harvey with notable experience at Google and Snowflake, dives into how generative AI is revolutionizing the legal industry. He highlights the profession's vast data and repetitive tasks as prime for AI integration. John emphasizes the need for lawyers to adapt to AI as a collaborative tool rather than expecting perfect answers. He shares real-world examples of time savings and explores the future, including automating NDAs. The conversation also touches on rethinking the billable hour and the transformative potential of AI in legal workflows.

Oct 14, 2025 • 41min
#79 - In House Career Growth: Being a Great Lawyer Isn't Enough
In this episode, Mary O'Carroll sits down with Rachel St. Peter, General Counsel at Nestlé Health Sciences US, to unpack a bold career move: stepping into legal ops mid-career to grow beyond the "good lawyer" baseline. From leading global transformation out of Switzerland to reshaping her executive presence and business fluency, Rachel explains how ops experience changed her leadership—and her trajectory. They also dig into the future of in-house legal: AI realities, law firm pricing shakeups, and what the next generation of GCs must bring to the table. In this episode: Why being a great lawyer isn't enough—and what Rachel did about it How a legal ops role built her executive presence and changed her leadership style What she's doing differently as GC—from tech tips in team meetings to smarter firm scoping The shift from client-service thinking to true cross-functional business partnership How law firm billing must evolve alongside AI adoption—and what real transparency looks like Advice for anyone considering a strategic detour: when to take the lateral move and why If you're thinking about how to future-proof your legal career—or how to lead with more impact—this episode will challenge the way you think about roles, risk, and reinvention. Follow Mary on LinkedIn Rate and review on Apple Podcasts

Sep 30, 2025 • 48min
#78 - The Joyful Legal Team
In this episode of Pearls On, Gloves Off, Mary sits down with Jacqueline Lee, Senior Vice President and General Counsel at Flynn Group, to unpack what it takes to lead legal, compliance, and risk functions at scale. Flynn is the parent company behind brands like Panera, Taco Bell, Wendy's, Planet Fitness, and more, with 75,000+ employees across the U.S., Australia, and New Zealand. Jacqueline shares her journey from big law to being unexpectedly tapped for a GC role just a year into her in-house life. Along the way, she reveals what's really changed (and what hasn't) in that transition — especially around how legal advice must shift to be more strategic, practical, and business-aligned. In this conversation, you'll learn: How to translate your legal skills for non-lawyer clients. Jacqueline stresses the importance of tailoring advice to how business leaders think and act — not how lawyers talk. Why "perfect information" is a myth in-house. You'll hear how GCs must balance risk, ambiguity, and the need to move fast. How to lead through crisis and uncertainty. Jacqueline's leadership during the pandemic reveals lessons in transparency, empathy, and restoring a feeling of control. How to demonstrate real value to the business. She explains her shift from narrative legal reports to visual dashboards, metrics tied to core business KPIs, and proactive reporting. The case for in-house litigation. Flynn handles much of its litigation internally; Jacqueline explains how they pick which matters to pursue internally vs. outsource — and why she still loves law. How to recruit, grow, and scale a legal team. We dig into her hiring philosophy, aligning on values, and the challenges of hybrid teams. Pricing and partnership with outside counsel. Jacqueline critiques the inefficiencies of hourly billing and shares how value-based arrangements can align incentives and build trust. If you're an aspirational in-house counsel or a legal leader grappling with how to prove impact, this episode is packed with insights you can start applying now. Follow Mary on LinkedIn Rate and review on Apple Podcasts

Sep 16, 2025 • 50min
#77 - Do Law Firms Actually Want Innovation?
Eddie Hartman has been disrupting legal long before it was fashionable. As Co-Founder of LegalZoom and now a Partner & Board Member at Simon-Kucher, he's worked with everyone from startups to AM Law 100 firms on pricing, innovation, and tech strategy. In this episode, Mary sits down with Eddie to talk about the legal industry's industry's uneasy relationship with change. From AI hype to the stubborn grip of the billable hour, they unpack why so many "innovations" fail, what clients actually mean when they ask about tech, and how law firms can evolve without losing their identity. In this episode: LegalZoom's Early Lessons: Why paralegals—not lawyers—were the first adopters, and what that reveals about confidence, adoption, and who really drives change. AI's False Start: The real reason 95% of AI initiatives fail—and why law firms may never fully embrace the efficiency it offers. Innovation vs Incentives: How law firms unintentionally kneecap their own innovation efforts—and what spinning off "tech incubators" says about the business model. What Pricing Really Signals: Why clients don't necessarily want cheaper—they want predictable, credible, and justified. And how fees send louder messages than firms realize. The Human Roadblock: From cultural protectionism to career incentives, why most resistance to change isn't technological—it's personal. If you're tired of the hype cycle and looking for a sharp, grounded view of where legal innovation actually stands, this conversation delivers. Follow Mary on LinkedIn Rate and review on Apple Podcasts

Sep 2, 2025 • 1h 2min
#76 - Why "Brilliance" Doesn't Sell: Rainmaker Strategies for 2025
When it comes to business development in professional services, Matt Dixon has spent decades decoding what actually works—and what doesn't. As a bestselling author and Founding Partner at DCM Insights, he's reshaped how companies think about sales. Now, with his new book The Activator Advantage, Matt turns his focus to the world of law, consulting, and other relationship-driven fields, where selling is often taboo—but still essential. In this episode, Mary sits down with Matt to unpack what top-performing partners do differently—and why it has nothing to do with cocktail parties or golf outings. Based on a global study of 3,500 partners, his research reveals a powerful new playbook for growing client relationships that's grounded in thoughtfulness, generosity, and strategic action. In this episode: The Five Partner Personas: From the Expert to the Confidant to the Activator, why most partners fall into outdated models—and what separates top performers. Why "Sales" Is a Dirty Word: Matt shares his story of getting cut off mid-presentation by a managing partner—and what it taught him about the legal mindset. What Clients Really Want: A direct line from clients themselves—what they wish partners would do more often, and why "waiting for the phone to ring" doesn't cut it anymore. The Power of Proactive Help: Why offering value before the invoice makes Activators so successful—and how it builds lasting loyalty. It's Not About Personality: Whether you're introverted or hate networking, this isn't about becoming someone else—it's about small shifts that make a big difference. The Role of the Firm: How BD and marketing teams can become activator enablers—and why leadership buy-in is key to scaling the model. If you've ever felt allergic to the idea of selling—or struggled to connect with clients beyond the brief—this episode offers a fresh, practical, and inspiring blueprint for doing BD differently. Get exclusive legal insights on healthcare's latest – only with Goodwin at HLTH. Follow Mary on LinkedIn Rate and review on Apple Podcasts

Aug 19, 2025 • 49min
#75 - Owning the AI Narrative (Before Someone Else Does)
When it comes to legal innovation, Jim Delkousis doesn't just have a front-row seat—he's one of the architects of change. As Founder and CEO of PERSUIT, Jim has spent almost a decade transforming how legal departments buy outside counsel services. With billions in legal work processed through the platform, he offers a rare, data-rich perspective on the shift from opaque hourly billing to value-driven, transparent legal spend. In this episode, Mary reconnects with Jim for a wide-ranging and insightful conversation about what's changing in legal procurement, why, and what it means for firms and clients alike. In this episode: The Death of the Billable Hour? How AI and data are eroding time as the currency of legal value—and what might replace it. The Power of Price Transparency: Why over 80% of matters on PERSUIT now use alternative fee arrangements, and what that says about the future of legal pricing. Reverse Auctions, Explained: The most controversial feature in PERSUIT—and why it's not necessarily a race to the bottom. When the Lowest Bid Doesn't Win: Jim shares the data behind client decision-making A GC's New Mandate: From cost center to value driver, what legal leaders need to prove to their CEOs—and how tech is helping them do it. If you've ever questioned the logic of hourly billing—or wondered how to move beyond it—this episode will challenge your assumptions and offer a roadmap forward. Follow Mary on LinkedIn Rate and review on Apple Podcasts


