In this video series from Paragon Legal, CEO Trista Engel sits down with general counsel from across industries for candid conversations about what it really takes to lead in today’s legal landscape.
These short, sharp interviews go beyond titles and headlines. Each episode explores the real decisions, challenges, and lessons shaping today’s in-house leaders.
From unexpected career pivots to navigating risk, managing legal teams, and driving business impact, GC Sidebar Season 2 highlights how general counsel are leading with clarity, creativity, and conviction in a rapidly changing environment.
Catch new episodes here as they drop.
As AI accelerates legal work, Carolyn Herzog, Chief Legal Officer at Elastic, is focused on a different question: what’s it costing us emotionally? In this episode of GC Sidebar, Carolyn shares why the human side of AI adoption—the fear, the cognitive load, the risk of losing collaborative moments to sheer speed—isn’t getting enough attention, even as legal teams race to keep up. She also reflects on one of the biggest surprises of the GC role: reporting to a boss who’s never practiced law, and learning to translate legal value into language an executive team will actually act on. Carolyn discusses the advice that reshaped her confidence early in her first GC role—being reminded she was hired for what she knows, not what she doesn’t—and how that same mindset now shapes her approach to organizational design, resourcing, and building a team built to look around corners.
It’s a candid conversation on AI’s emotional toll, executive communication, and leading with confidence through constant change. Watch the full episode now.
As AI reshapes both legal and creative work, Jonathan Anschell, Chief Legal Officer at Mattel, is focused on a different question: how do you harness the technology without losing the judgment behind it? In this episode of GC Sidebar, Jonathan shares how he sees AI as an accelerant for legal work and an ideation engine for creative teams, while staying vigilant about intellectual property, safety, and privacy at a company built on iconic brands. He also reflects on the most valuable lesson of his career—the discipline of listening, letting silence sit, and hearing what’s really behind the other side’s position before responding. Jonathan discusses joining Mattel during its transformation from toy maker to IP powerhouse, and how flexible legal talent has helped his lean team build new capabilities, like a rights management system, without losing focus or growing fixed costs.
It’s an engaging conversation on AI, listening, and leading legal through a company’s creative reinvention. Watch the full episode now.
As uncertainty becomes the norm for legal teams, Teresa Shea, Chief Legal Officer at Utz Brands, is focused on a different question: how do you prepare for the disruptions you can’t predict? In this episode of GC Sidebar, Teresa shares why her team has built out “special situations” planning—deliberate frameworks for everything from weather events to shifting nutrition regulations—so the company can respond with calm instead of chaos. She also discusses the advice from her CEO that reshaped how she shows up in the room: introducing herself first as an executive at Utz, not as the company’s lawyer, and bringing her whole brain to the business rather than just her legal opinion. Teresa reflects on building a legal team from the ground up as Utz’s first in-house hire, how she’s learned to balance insourcing expertise with flexible legal support, and why her background as a teacher shapes the way she leads.
It’s a grounded conversation on proactive planning, enterprise leadership, and what it takes to build a legal function from scratch. Watch the full episode now.
As legal teams rush to adopt AI, Claudia Regen, General Counsel at Spotless Brands, is focused on a different question: what happens after adoption? In this episode of GC Sidebar, Claudia shares why AI governance can’t be an afterthought—it has to be built into the work itself, not bolted on once the tools are already in place. She also discusses why so much of the GC role is less about legal analysis and more about facilitation, getting finance, product, and sales to speak the same language so decisions can actually get made. Claudia reflects on the career advice that’s shaped her approach to growth—becoming comfortable being uncomfortable—and how she’s used flexible legal talent to free her core team for business-critical work while giving them new opportunities to develop.
It’s a thoughtful conversation on AI governance, cross-functional leadership, and what it takes to lead legal through constant change. Watch the full episode now.
As AI reshapes the legal landscape and legal teams face growing pressure to do more with less, Kevin Yung, General Counsel at MasterClass, is focused on a different question: how does a lean legal team scale without scaling headcount? In this episode of GC Sidebar, Kevin shares why he believes AI will augment legal teams rather than replace them, and why understanding the technology is now as essential as understanding the law itself. He also discusses the non-legal work that surprised him most about the GC seat—becoming a product evaluator and buyer for the tools his team relies on—and why hiring for potential and adaptability matters more than hiring for a résumé. Kevin reflects on the career-changing risk someone once took on him, how he uses flexible legal talent to both support and develop his team, and what he’s learned about building a small legal function that moves as fast as the business around it.
It’s a candid conversation on AI, resourcing, and what it really takes to lead legal at a fast-growing company. Watch the full episode now.
As legal teams navigate rapid change driven by AI, evolving expectations around ethics, and increasing pressure to act as strategic business leaders, Nishat Ruiter, General Counsel at TED Conferences, is focused on a different question: how can lawyers build the judgment, creativity, and confidence needed to lead through uncertainty? In this episode of GC Sidebar Season 2, Nishat shares the inspiration behind TED Law, a new learning initiative designed to help legal professionals strengthen critical thinking, ethical reasoning, and AI readiness. She also discusses why legal leaders should play a more active role in advocacy, how GCs can balance competing stakeholder interests while serving the best interests of the organization, and why listening to your own intuition can be one of the most important career skills you develop.
It’s a thoughtful conversation on leadership, innovation, and the evolving role of lawyers in a rapidly changing world. Watch the full episode now.
As legal teams navigate growing expectations around technology, risk, and business partnership, Doe Gregersen, General Counsel at Nav Technologies, is focused on a different challenge: how can legal leaders build the trust and relationships that allow them to influence decisions before they’re made? In this episode of GC Sidebar Season 2, Doe shares her perspective on why the role of legal isn’t to protect the business from itself, but to help the business move forward by understanding, contextualizing, and managing risk thoughtfully. She also discusses why relationships are foundational to effective in-house leadership, how legal teams can shift from being perceived as blockers to strategic partners, and why the AI conversation may be generating more noise than practical adoption for many organizations today.
It’s a thoughtful conversation on leadership, influence, and what it takes for legal teams to become true business partners. Watch the full episode now.
As businesses face growing complexity and pressure to move faster, Alisha Cieslak, former Chief Legal and Risk Officer at Gordon Food Service, is focused on a different challenge: how can legal leaders build teams and systems that help the business scale strategically, not just manage risk? In this episode of GC Sidebar Season 2, Alisha shares her perspective on why modern GCs must operate as business leaders first, translating legal issues into business impact, growth, and operational strategy. She also discusses why letting go of perfection is essential in fast-moving environments, and how strong judgment and adaptability build trust with leadership teams.
It’s a thoughtful conversation on leadership, resourcing, and what it takes to build a modern legal function that can grow with the business. Watch the full episode now.
As businesses move faster and complexity increases, Lisa Gorman, former Chief Legal Officer at Eventbrite, is focused on a different question: how can legal teams become trusted partners early enough to help shape decisions, not just react to them In this episode of GC Sidebar Season 2, Lisa shares her perspective on embedding legal earlier into the business, building trust that brings legal into conversations sooner, and why some of the most effective legal work is often invisible. She also discusses how redesigning systems can prevent issues before they arise, why stepping outside your comfort zone can reshape your leadership perspective, and how flexible legal talent can help teams stay focused on the work that truly requires judgment.
It’s a thoughtful conversation on leadership, trust, and what modern legal partnership really looks like. Watch the full episode now.
As complexity accelerates and uncertainty becomes the norm, Rishi Varma, Chief Legal and Ethics & Compliance Officer at Cargill, is focused on a different challenge: how do you build a legal function that can think, adapt, and lead at scale? In this episode of GC Sidebar Season 2, Rishi shares his perspective on navigating ambiguity, combining AI-enabled systems with human judgment, and why great GC leadership isn’t about having all the answers. He also explores how slowing down helps teams move faster, and how structuring talent around capability, not tenure, unlocks stronger performance.
It’s a thoughtful conversation on leadership, technology, and building legal teams equipped for today’s complexity. Watch the full episode now.
As legal teams rethink how they approach risk, Luis Machado, General Counsel at TopBuild, is focused on a different question: how do you help the business make better decisions, not just safer ones? In this episode of Season 2 of GC Sidebar, Luis shares his perspective on why risk isn’t something to eliminate, but something to understand, frame, and navigate. He also talks about building legal teams that are embedded in the business, not operating on the sidelines.
It’s a grounded conversation on leadership, resourcing, and what it takes to be a true business partner in today’s environment. Watch the full episode now.
As AI reshapes how legal work gets done, Jenn Wall, General Counsel at Intrinsic (Alphabet), is focused on a critical question: how do you build real judgment in the next generation of lawyers?
In this episode of Season 2 of GC Sidebar, Jenn shares her perspective on training legal talent in an AI-driven world, building teams that are trusted business partners, and leading through rapid technological change. It’s a thoughtful conversation on leadership, development, and the future of in-house legal teams. Watch the full episode now.
From protecting groundbreaking investigations to preparing for increased risks facing journalists, Fabio Bertoni, General Counsel of The New Yorker, operates at the intersection of law, media, and mission.
In our first episode of Season 2 of GC Sidebar, Fabio shares what’s top of mind this year. It’s a candid conversation about judgment, responsibility, and leading a legal team under pressure. Watch the full episode now.
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