Pearls On, Gloves Off

Kathy Dockry, a seasoned leadership coach and former CEO of a major British energy company, shares insights on what it takes for high-achieving professionals to stand out. She emphasizes that simply doing your job well isn't enough for promotions; mastering the art of influence and storytelling is crucial. Kathy discusses the importance of developmental coaching and feedback, how learning agility predicts success, and offers strategies for self-promotion and articulating value, all aimed at elevating careers in competitive environments.

In this engaging discussion, Matt Sunderman, CEO of Harbor Global and a veteran of the legal industry, shares his insights on law firm transformation. He reveals the spectrum of readiness among firms, from those poised for change to those lagging behind. Matt emphasizes that while technology is a catalyst for transformation, it's not the sole answer. He also dives into market consolidation trends and the implications of KPMG's entry into the U.S. legal market, highlighting the evolving landscape and the urgent need for innovation in legal services.

Frances Pomposo, Senior Director of Legal Technology Solutions at Cisco, offers deep insights into the evolving landscape of legal operations. She and her host discuss the fading role of the 'strategic generalist' and the rise of specialized positions like data analytics. They dive into hiring challenges, debating the pitfalls of flawed recruitment processes. Additionally, the conversation unveils the trend of companies favoring external consultants over in-house teams, and highlights the pressing need for global standards in legal ops roles.

Andy Cooke, General Counsel at TravelPerk, shares his visionary insights on evolving legal services with AI innovations. He discusses the shift from outdated chatbots to advanced AI solutions, emphasizing the importance of customer-centricity in the legal sector. Cooke addresses the need for legal teams to embrace experimentation and diverse perspectives to stay relevant. He also highlights the critical role of data in decision-making and the transformation of legal training, urging future lawyers to adapt to an AI-driven landscape.

In this episode, Mary sits down with Vanessa Wu, the General Counsel at Rippling—a fast-growing platform unifying HR, IT, finance, and more for businesses around the globe. From eliminating contract negotiations by design to harnessing AI for everyday legal work, Vanessa shares how she’s freeing up her team for the most important, high-level tasks. She also opens up about navigating a crisis when Silicon Valley Bank collapsed and Rippling had to hustle a weekend financing—all thanks to smart “North Star” planning long before the alarm bells rang. Topics: Maintaining a “no-redline” policy for 20,000+ customers—and why sales loves it How fresh thinking on AI (and a PowerPoint from a 9-year-old!) sparked new ways of working Why planned redundancy and constant readiness saved Rippling’s payroll operations Rethinking the legal team’s role as a “future-forward” function rather than a cost center Fostering curiosity and encouraging experimentation—especially when it feels like “cheating” If you enjoyed this conversation, be sure to subscribe to Pearls On, Gloves Off for more candid discussions with leaders shaping the legal and corporate landscape. We’d love to hear your thoughts—connect with us on social media and join the conversation! Goodwin at HumanX Follow Mary on LinkedIn Rate and review on Apple Podcasts

“Flexibility is here to stay.” – Emily Botello In this episode, Mary chats with Emily Botello from CBRE about how the legal industry is reinventing its office spaces. From single-size offices and neighborhoods of shared desks to seamless technology and thoughtful change management, Emily shares what’s working, what’s not, and how legal teams are adapting to a world where no two days look the same. Topics: Redefining the office with single-size standards and more collaborative designs Setting “anchor” days and neighborhoods to encourage in-person connections Ensuring plug-and-play tech and easy reservations to match the convenience of home setups Involving everyone—partners, associates, and naysayers alike—in mapping the path to a better workspace If you enjoyed this conversation, be sure to subscribe to Pearls On, Gloves Off for more candid discussions with leaders shaping the legal and corporate landscape. We’d love to hear your thoughts—connect with us on social media and join the conversation!   Follow Mary on LinkedIn Rate and review on Apple Podcasts  

  “Sometimes the right answer for Anthropic would be things that 99% of tech companies wouldn’t even consider. You have to be appropriately open to weirdness—not weirdness for the sake of weirdness, but tied to what we’re trying to achieve in the world.” —Brian Isreal, GC, Anthropic In this episode, Mary sits down with Brian Israel, General Counsel at Anthropic, to explore what it’s like to operate at the legal and cultural frontier of AI. From building a hypergrowth legal team to designing a legal “front end” that prioritizes user experience, Brian shares his perspective on leadership, innovation, and navigating the edge of the possible. Topics covered include: Anthropic’s mission: Building a safer transition to transformative AI and how that shapes the company's operations and values. Legal team culture: What it means to be “appropriately open to weirdness” in service of a larger mission. Hypergrowth dynamics: Lessons from scaling a legal team from one person to 27 in just two years. Front-end legal design: Translating complex legal concepts into actionable advice for fast-moving teams. AI in legal workflows: How Anthropic’s own tool, Claude, has become an integral member of the legal team. Ownership and leadership: Why accountability and agency are critical in a high-stakes environment. Brian’s journey to Anthropic—from NASA to startup land—is as unconventional as his approach to law. Tune in to hear his insights on culture, collaboration, and why the best legal teams are both technically excellent and human-centered. Catch the full conversation now, and don’t miss Brian’s take on how AI is poised to redefine the legal profession. Connect with us and join the conversation: Follow Mary on LinkedIn Rate and review on Apple Podcasts  

This special episode was recorded live at Goodwin's Tech Retreat in San Francisco, where Mary sits down with Phil Mazzara, General Counsel of Astera Labs, to explore the evolving role of the general counsel in today's rapidly changing technological landscape. Phil's journey is nothing short of extraordinary. Before becoming an attorney, he spent over a decade on active duty as a Navy pilot, bringing a unique perspective to the legal field. With a JD/MBA from Stanford, Phil skipped the traditional law firm route and went straight in-house. Prior to joining Astera Labs, he served as General Counsel and Secretary at Innovium, where he oversaw multiple venture financings, negotiated critical commercial agreements, settled bet-the-company litigation, built a robust IP portfolio, and ultimately led the company through its $1.1 billion acquisition by Marvell Technology. At Astera Labs, Phil played a pivotal role in taking the company public in March 2023, a challenging year for capital markets. Under his legal guidance, Astera Labs has been riding the AI wave, focusing on AI infrastructure and experiencing significant growth. In this engaging live conversation, Phil and Mary delve into: ·         The Journey to IPO: Phil shares his experiences taking Astera Labs public in a tough market, the importance of choosing the right outside counsel, and how Goodwin played a crucial role in their successful IPO. ·         AI in Legal Practice: How AI is impacting the legal profession, both within corporate legal departments and in law firms, and the potential future applications of AI in complex legal work. ·         The Evolving Role of General Counsel: Discussing how the general counsel's role has expanded beyond traditional legal services to include compliance, business strategy, and being a key advisor to the executive team. ·         Building Strong Law Firm-Client Relationships: Phil offers advice to law firms on how to better serve their clients, emphasizing the importance of understanding the client's business deeply, being proactive, and building trust. ·         Quality of Legal Work and Service: How to measure and ensure high-quality legal services, the significance of responsiveness, attention to detail, and open communication. ·         Advice for Junior Lawyers: The value of seeking opportunities to engage directly with clients, asking questions to understand their business, and stepping up to deliver work product in front of senior executives. ·         Leadership Lessons from the Navy: Phil reflects on how his experience as a Navy pilot informs his approach to leadership, project management, and the use of checklists to ensure quality and reduce errors. ·         The Future of Legal Practice: A candid discussion on how AI and technological advancements are shaping the legal industry, the enduring importance of judgment and counsel, and the skills lawyers will need to succeed in the future. If you're interested in the intersection of law, technology, and business—or if you're curious about how military experience can translate into corporate leadership—this live episode is a must-listen. Connect with us and join the conversation: Goodwin Exhibit A Follow Mary on LinkedIn Rate and review on Apple Podcasts  

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O’Carroll, Chief Operating Officer at Goodwin. Today, Mary dives deep with Chris Grant, Head of Legal Market Engagement at HSBC, to unravel the evolving landscape of the legal industry. Chris Grant isn’t your typical legal professional. Frustrated by the glacial pace of change in an industry resistant to innovation, Chris has spent his career challenging the status quo. From his early days in private practice to his current role at HSBC, he’s been a relentless advocate for efficiency and transformation in legal services. He’s built ecosystems supporting next-generation legal solutions, notably at Barclays Eagle Labs, and has been recognized in the Financial Times Innovative Lawyers Top 10 Entrepreneurs and the Legal 500 GC Power List. In this episode: ·         The Frustration That Fuels Change: Chris shares how his early career disillusionment ignited a passion for legal transformation. ·         Is Change Finally Happening? A candid discussion on whether the legal industry is genuinely evolving or just paying lip service. ·         The Death of the Billable Hour: Will we ever see it? Chris offers a provocative take on alternative fee arrangements—or as he calls them, Effective Fee Arrangements (EFAs). ·         Trust Issues: Delving into the often-unspoken lack of trust between clients and firms, and how it hinders progress. ·         Data as the New Gold: How leveraging data can revolutionize legal services, from pricing to service delivery. ·         Advice for In-House Teams and Firms: Practical steps both sides can take to build trust, embrace innovation, and deliver real value. ·         The Role of Technology: Why AI is more than just a buzzword and how it’s accelerating conversations that were stagnant for decades. ·         Future Gazing: Chris’s vision for the next 5-10 years in legal services, and why he believes the time for change is now. If you’re as passionate about legal transformation as Mary and Chris, or just curious about the seismic shifts shaking up the industry, this episode is a must-listen. Follow Mary on LinkedIn Rate and review on Apple Podcasts

Reena SenGupta, a legal industry thought leader with nearly 30 years of experience, discusses the transformative changes in law firms. She explains how generative AI is reshaping the legal landscape, making practices more efficient. Reena highlights the evolution of legal rankings and their importance in reflecting true client value. She advocates for new success metrics that prioritize innovation over profits and emphasizes the need for a revamped legal education to better prepare future professionals for a changing market.