This week I’m joined by Jeff Arnold: five-time bestselling author, founder of RightSure (North America’s most awarded insurance firm), and a guy who somehow turned standing next to a serious CEO at a drink fountain into a leadership lesson.

We talk about why self-deprecating humor is the best humor, why “yes, and” belongs in your boardroom and not just your improv class, how Jeff kills his own ego every time he writes a book, and the story behind the most expensive speeding-ticket photo in Arizona history. Bring tissues. You’ll need them for laughing.

Key Topics

• Self-deprecating humor as a leadership trust-builder
• The “yes, and” philosophy from improv, applied to business
• Reframing failure as forward motion
• Using humor to deliver hard news without losing authenticity
• Writing 12 books and learning to kill your own ego on the page
• Humor and AI: deploying technology without losing the human side of leadership
• Rebranding insurance agents as “famously friendly humans”
• Knowing your audience: when to dial humor up, and when to dial it down
• The line between self-deprecating humor and “punching down”

Guest Advice

Lead with self-deprecating humor before anyone else gets the chance to make you the joke. It signals confidence, not weakness, and it’s the fastest way to build trust with a team.

Resources Mentioned

• RightSure Insurance
• Jeff’s book, AI Forward Leadership
• Jeff has written 12 books total, 5 of them bestsellers https://jeffarnold.com/books/
• Jeff Arnold's Website

Additional 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.ca

Thank 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 Davis
Edited by Chris @ Wider View Studios