Lisa Pagotto
Founder & CEO of Crooked Compass, Guiding Personal Reinvention Through Experience
Lisa Pagotto Podcast Episodes
Humor In The C-Suite
The Flight of Authenticity: How Lisa Pagotto Leads with Humor in the World's Most Extreme Destinations
May 12, 2026
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About this episode
What does leadership look like when your boardroom is a remote jungle and your team is scattered across time zones navigating geopolitical complexity? For Lisa Pagotto, founder of Crooked Compass, it looks like authenticity, resilience, and a finely tuned sense of humor. In this episode of Humor in the C Suite, Kate Davis sits down with Lisa to explore how the principles that make Crooked Compass extraordinary — cultural respect, genuine connection, and bold decision-making — translate directly into a leadership philosophy that any leader in any industry can learn from.
Key Topics Covered
Lisa and Kate explore how humor functions as a genuine leadership tool in high-stakes, high-complexity environments — not as performance, but as a way of managing expectations, building trust, and keeping teams grounded when the terrain is genuinely unpredictable. They dig into the cultural intelligence required to know when humor works and when it doesn't — how some cultures welcome levity while others require a more measured approach, and why reading that distinction correctly is a core leadership skill. Lisa talks about how sharing mistakes and failures with humor makes her more relatable to both her team and her clients, and why that vulnerability is actually one of her greatest strengths as a leader. They also cover what Crooked Compass by Air taught Lisa about pivoting under pressure, how she leads a remote team with authenticity and openness, and why she believes the future belongs to those who dare to do things differently.
