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

Pearls On, Gloves Off: The Legal Innovation Podcast

Mary O'Carroll
Legal Operations
Artificial Intelligence
Legal Technology
Law Firms
General Counsel
Change Management
Generative AI
Transformation
Ironclad
Goodwin
M&A
Legal Recruiting
Mentorship
Billable Hour
Legal Ops
Venture Capital
Leadership
Workday
Legal Innovation
Contracts Lifecycle Management

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.

PublishesTwice monthlyEpisodes105Founded4 years ago
Number of ListenersCategories
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Artwork for Pearls On, Gloves Off: The Legal Innovation Podcast

Latest Episodes

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... more

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 lawyer... more

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 completel... more

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 waiti... more

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Recent Guests

Adam Sterling
Stanford Law School's Associate Dean of Executive Education and Strategic Partnerships
Stanford Law School
Episode: #104 - Flight Simulators for Lawyers: The Rise of the Legal Engineer and How the Profession Learns
Irene Liu
Executive Director of the Stanford Law School AI Initiative
Stanford Law School
Episode: #104 - Flight Simulators for Lawyers: The Rise of the Legal Engineer and How the Profession Learns
Larry Richard
Psychologist and author
Author of Thin Skinned: Why Lawyers Are So Low in Resilience
Episode: #103 - The Lawyer Personality Unpacked: What the Data Says After 32 Years of Research
Ryan Daniels
Co-founder and CEO of Crosby
Crosby
Episode: #102 - Inside Crosby: The AI Law Firm Rethinking How Legal Work Gets Done
Darth Vaughn
Associate General Counsel and Managing Director of Policy and Legal Ops at Ford Motor Company
Ford Motor Company
Episode: #101 - Ford's Warning Shot: Adapt or Get Left Behind
Eric Dodson Greenberg
Executive Vice President, Chief Legal Officer and Corporate Secretary at Cox Media Group
Cox Media Group
Episode: #100 - The Future of Legal Is Already Here - A Conversation with CLO Eric Greenberg
Nick Fleisher
Co-founder and CEO of Sandstone
Sandstone
Episode: #99 - Who Is Sandstone? Inside Legal Tech's Most Talked-About Company
Anna Richards
Head of Community at Brightflag
Brightflag
Episode: #98 - Anna Richards
James O'Dowd
Founder and CEO of Patrick Morgan, talent advisory and intelligence firm for professional services
Patrick Morgan
Episode: #97 - The Senior Talent Problem Nobody Wants to Talk About

Host

Mary O'Carroll
Host of the show, conversational interviewer focused on AI, governance, and transformation in legal operations and technology.

Reviews

4.8 out of 5 stars from 50 ratings
  • Great Content for any Legal Ops Professional

    Mary always provides insightful content for which I am eagerly awaiting to learn with each podcast. I learn so much and receive the reinforcement needed to become a better Legal Ops professional. Thank you Mary!!

    Apple Podcasts
    5
    St Johns CR210
    United States4 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Sponsorships feel integrated with real-world tooling and case studies
The episodes balance strategic thinking with practical, scalable tools
Mary delivers consistently insightful conversations that keep me ahead on legal ops and AI
Guests bring deep expertise from in-house and tech-enabled legal teams

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

#104 - Flight Simulators for Lawyers: The Rise of the Legal Engineer and How the Profession Learns
Q: Could you tell me briefly about your roles and what you do at Stanford Law School?
Adam Sterling explains he is Associate Dean for Executive Education and Strategic Partnerships, overseeing programs for executives and leaders, plus the Rock Center for Corporate Governance. Irene Liu describes herself as Executive Director of the AI Initiative, leading AI education and policy-oriented work, with experience as a former general counsel and government attorney. The host sets the stage for discussing the legal engineering program and its goals.
#101 - Ford's Warning Shot: Adapt or Get Left Behind
Q: What would you prioritize when building an innovation-friendly legal organization?
Priorities include democratizing access to tools, maintaining safety and governance, funding moon-shot projects with clear ROI, and continuously educating teams so that incremental productivity gains compound over time.
#101 - Ford's Warning Shot: Adapt or Get Left Behind
Q: What incentives drive firms vs. in-house teams, and how can they align with client ROI?
Incentives historically rewarded hours rather than outcomes; aligning incentives requires outcome-based pricing, shared risk, and central governance of investments to ensure real ROI and sustained innovation; clients will push firms to innovate or risk losing business.
#101 - Ford's Warning Shot: Adapt or Get Left Behind
Q: How do you see AI changing the core competencies of lawyers and the way work is managed?
AI shifts the focus from generating content to applying judgment and governance, enabling lawyers to work more efficiently while maintaining accountability; the aim is to know when the machine can do the work and when human expertise is essential.
#101 - Ford's Warning Shot: Adapt or Get Left Behind
Q: What is your role at Ford and how has it evolved over time?
My role centers on transforming how Ford delivers legal services, combining policy, operations, and tech to move from day-to-day management to upstream, strategic transformation that supports fast decision-making and better outcomes for the business.

Audience Metrics

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Frequently Asked Questions About This Podcast

What is This Podcast about and what kind of topics does it cover?

This show centers on the intersection of law, technology, and operations, with a heavy emphasis on AI's impact on in-house legal teams, governance, and how law firms and corporate legal departments adapt to new delivery models. Across episodes, discussions frequently explore AI governance, legal ops, the rise of AI-native workflows, and the evolving roles of senior lawyers and legal engineers within large organizations. A standout trait is the practical focus on real-world implementations—ranging from contract processing and e-discovery to centralized AI-enabled legal centers of excellence—framed by leadership perspectives from major enterprises and pioneering legal tech firms. The format tends to blend strategic thinking with hands-on insi... more

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1. Dwarkesh Podcast
2. Hard Fork
3. The Every Podcast
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this podcast launched 4 years ago and published 105 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on this podcast?

Recent guests on this podcast include:

1. Adam Sterling
2. Irene Liu
3. Larry Richard
4. Ryan Daniels
5. Darth Vaughn
6. Eric Dodson Greenberg
7. Nick Fleisher
8. Anna Richards

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