Legal Leaders

Ali Rafie

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Hear from industry leaders in the legal and business world.

2D AGO

EP 35: Leading Legal Teams & Managing Yourself as GC with Executive Coach Dennis Adsit

In this episode, I sit down with Dennis Adsit, an executive coach with over a decade of experience helping leaders navigate transitions and build high-performing teams. Dennis holds a PhD in industrial psychology and has coached everyone from startup founders at Techstars to C-suite executives, with prior experience leading Six Sigma implementation and global call centers at Intuit. Dennis reveals why most lawyers' resumes fail: they focus on credentials and responsibilities instead of business impact. He introduces his WAS-DID-IS framework, which structures your story around the situation you faced, the actions you took, and the measurable results you delivered. We explore his four-pillar model of executive effectiveness: setting strategic context, executing efficiently, building talent, and managing yourself. Dennis explains how AI is changing leadership priorities, making the "generosity gene"—your ability to celebrate your team and create connection—more critical than ever for retaining talent and maintaining productivity. For lawyers transitioning from firms to in-house roles or moving into general counsel positions, Dennis breaks down the specific mindset shift required: from individual contributor solving legal problems to leader building platforms for others to succeed. He also offers tactical advice for early-career professionals on saying yes to diverse opportunities and becoming known as reliable problem-solvers. About Adist Insights:adsitinsights.com https://medium.com/@dennis_adsit/lawyers-and-the-mystery-of-the-missing-case-efffd3106814

42 min
FEB 4

EP 34: Dan Haley, CLO of Flock Safety: Building & Leading Legal Teams at High-Growth Companies

I spoke with Dan Haley, Chief Legal Officer of Flock Safety, to walk through a career that spans nearly a decade in Big Law and senior legal leadership roles at some of the fastest-growing technology companies in the country. Dan shares what it’s really like to make the transition from law firms to in-house, including the tradeoffs, surprises, and lessons he learned along the way. We talk about navigating high-stakes moments such as major acquisitions, IPOs, and scaling legal teams through periods of rapid growth and uncertainty. Dan also discusses his current role at Flock Safety, the legal and constitutional questions surrounding public safety technology, and how he thinks about privacy, the Fourth Amendment, and responsible innovation from the CLO seat. Throughout the conversation, Dan reflects on career decision-making, leadership, and why focusing on doing excellent work, staying open to unexpected opportunities, and building genuine professional relationships can matter more than rigid long-term planning. This episode is relevant for law students, associates, and in-house lawyers interested in high-growth tech, legal leadership, and building a meaningful career over time.

55 min
JAN 19

EP 33: Building the Future of Legal AI with Justin McCallon, Founder of StrongSuit

Justin McCallon is the Founder and CEO of StrongSuit, an AI platform built to modernize and accelerate core legal workflows. Justin started his career as a practicing attorney before leading large-scale analytics, transformation, and AI initiatives at AT&T and DIRECTV. In our conversation, we cover his path from law to consulting to building a legal AI company, what he’s seeing in the legal tech market right now, and how legal teams are actually adopting AI in practice. We also dig into StrongSuit’s product: AI-driven legal research, drafting, and document review, plus how StrongSuit compares to legacy research platforms and where Justin believes the biggest ROI is for litigators. Justin also shares a bold prediction: by the end of 2026, it may be possible to automate 50–99% of common litigation tasks with AI agents—and what that means for lawyers building careers in a rapidly changing profession. Www.Strongsuit.com #LegalTech #AI #Litigation #LegalAI #LawSchool #InHouse #LawFirm #LegalInnovation #Startup #JD

39 min
JAN 12

EP 32: Autonomous Vehicle Regulation: A Conversation with Ian Poirier (Toyota Research Institute)

Ian Poirier is the Associate General Counsel at Toyota Research Institute (TRI), where he works at the intersection of autonomous vehicles, robotics, safety, and policy. We talk about how autonomous vehicle regulation has evolved over the past decade, including Ian’s experience moving from Lyft’s early AV efforts to Toyota’s long-term research and safety programs. Along the way, he explains why one of the hardest questions in autonomy remains defining what “safe enough” actually means when formal standards lag behind the technology. We also walk through Ian’s in-house career path—from UCSF Law to Wikimedia, Lyft, and ultimately Toyota—and the unconventional choices that shaped it. Ian reflects on why mastering legal fundamentals, taking on responsibility early, and being willing to operate without formal training or process became the foundation for his career in emerging technology.

42 min
JAN 1

EP 31: Coupa CLO Julia Taylor: From BigLaw to Eventbrite's $1.8B IPO

Julia Taylor is the Chief Legal Officer at Coupa and a Berkeley Law alum. We unpacked her path from Big Law to becoming the first lawyer at Eventbrite, where she spent nearly twelve years and helped guide the company through its $1.8B IPO. Julia reflects on her early influences, including her time working on Capitol Hill for Senator Dianne Feinstein and Jerry Brown, and how those experiences shaped her pragmatic, solutions-oriented approach to leadership. We also talked about what it actually means to succeed in-house. Julia explains why deeply understanding the business, building trust across teams, and staying calm under pressure are the traits that matter most, especially during high-stakes moments. The conversation also covers some of the most challenging moments of Julia’s career, including leading through COVID-era layoffs, navigating risk when Eventbrite unexpectedly became a platform for vaccine registration, and knowing when it was time to step aside to let the next generation of leaders rise. Julia offers candid advice for law students, associates, and in-house lawyers on career strategy, risk tolerance, and why being “ruthlessly practical” is often the key to long-term success.#LawSchool #LegalLeadership #LegalTech #Coupa #Eventbrite #IPO #BigLaw

1 hr
12/03/2025

EP 30: Reflecting on 15 Years at Microsoft with Jason Barnwell

Jason Barnwell just joined Agiloft as Chief Legal Officer after 15 years at Microsoft, where he most recently served as GM and Associate General Counsel for Monetization and Business Planning. I spoke with Jason about his career path from MIT engineering grad to software engineer to leadership at one of the world's leading tech companies. We discussed his work driving digital transformation within Microsoft's legal department and his philosophy on developing legal talent, including his concept of getting to "minimum viable lawyer" as quickly as possible. Jason also shared insights on how technical backgrounds enhance legal practice and his perspective on AI in the profession. His view: the technology isn't the challenge, it's getting legal organizations to adapt their structures and incentives. #LegalTech #Microsoft #Agiloft #InHouseCounsel #LegalLeadership #DigitalTransformation #BerkeleyLaw #LawSchool #CLM

53 min
08/08/2025

EP 29: Building a Legal Tech Brand with Colin Levy & Innovating the Future of Law

I spoke with Colin Levy, General Counsel at Malbec, an innovative CLM company. Colin shares his in-house journey, his passion for legal technology, and how he's helping bridge the gap between law and tech. Colin discusses the importance of building a personal brand, embracing AI in the legal industry, and the future of law schools adapting to tech innovations. He also offers insightful advice for new lawyers looking to break into the legal tech world. Tune in for a conversation filled with career insights, tech trends, and actionable advice for lawyers and legal professionals! Links: Colin Levy's Website: https://www.colinslevy.com Malbec.io - Legal Tech Solutions: https://www.malbek.io/

40 min
07/29/2025

EP 28: The Truth About AI in BigLaw: Why Culture Beats Tech and Veterans Are Leading the Way w/ Reed Smith Chief Innovation Officer David Cunningham

David Cunningham is the Chief Innovation Officer at Reed Smith LLP, where he leads legal tech transformation for 2,000+ lawyers across 34 offices. But his focus goes far beyond technology—he’s rethinking the culture and workflows that shape how legal work gets done. With a background in legal operations and data analytics, David has become one of the leading voices in the push for practical, scalable innovation in Big Law. He’s also the founder of Legal Metrics, a nonprofit initiative improving how firms and clients measure performance. In this episode, David pulls back the curtain on what firms are really doing with AI and how change actually happens at scale. We talk about the biggest barriers to adoption (hint: it’s not the tools), how some seasoned partners are leapfrogging junior lawyers in AI use, and what law firms can learn from tech companies. We also explore: -How David’s background in client-facing innovation shapes his work inside the firm -What “working backwards from the client” looks like in Big Law -Why the hardest part of innovation is behavior—not technology -The metrics that actually matter for modern legal teams -How law students and associates can position themselves as innovation leaders -If you’re curious about the future of legal work and what’s happening behind the scenes at some of the world’s top firms, this episode is for you. 🎧 Subscribe if you enjoyed the episode! #LegalTech #Innovation #BigLaw #AI #LegalLeadership #FutureOfLaw #LegalOps #LawFirmStrategy

39 min

Hear from industry leaders in the legal and business world.

Creator

Ali Rafie
Years Active

2024 - 2026
Episodes

35
Rating

Clean
Copyright

© Ali Rafie
Show Website

Legal Leaders