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.
About Lisa Pagotto
Lisa Pagotto spent 24 years building one of the most distinctive travel companies in the world. Crooked Compass specializes in immersive, culturally respectful journeys to remote and lesser-known destinations — experiences that prioritize authenticity over manufactured itineraries and meaningful connection over mass tourism. Lisa appeared on Shark Tank Australia and when COVID shut down global travel, she pivoted by launching Crooked Compass by Air — exclusive aerial tours of Australia, including private aircraft landings at Sydney Airport during its shutdown. She is also a sought-after keynote speaker on resilience, authentic leadership, and backing yourself when the world says no.
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.
“Sharing failures or mistakes or errors and turning them into humor just makes it more relatable.” — Lisa Pagotto
Lisa’s Advice for Leaders
Lead with authenticity before you lead with authority. The leaders who create genuine trust are the ones willing to show their humanity — including their mistakes. Use humor intentionally and read your audience carefully, especially across cultures. Some environments welcome levity immediately; others require you to earn it slowly. Know the difference and adjust accordingly. And when things go sideways — because they will — find the humor in it. Not to minimize the situation, but to keep your team grounded and remind them that imperfection is part of the process.
About Crooked Compass
Crooked 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.com
Connect with Lisa Pagotto 🌐 Crooked Compass Website 📼 Youtube
Connect with Kate Davis 📧 kate@katedavisca.com 🎙️ Humor in the C Suite — available wherever you get your podcasts
