The Flight of Authenticity: How Lisa Pagotto Leads with Humor in the World's Most Extreme Destinations

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 CoveredLisa 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."Sharing failures or mistakes or errors and turning them into humor just makes it more relatable." — Lisa PagottoAbout Crooked CompassCrooked Compass is a multi-award-winning experiential travel company specializing in immersive journeys to remote and lesser-known destinations across the globe. Every experience is designed to prioritize cultural integrity, authentic connection, and meaningful exploration — free from the constraints of mass tourism. Visit https://www.crooked-compass.comConnect with Lisa Pagotto 🌐 Crooked Compass Website 📼 YoutubeAdditional Links & Resources:Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!Learn more about me and my work at katedavis.caThank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. Hosted by Kate DavisEdited by Chris @ Wider View Studios