Key topics: Leadership development in the age of AI · humor as an icebreaker in corporate IT leadership · Who are the "new zombies"? · why empathy and emotion are what AI still can't replicate · AI hallucinations and the limits of large language models · curiosity as a leadership trait · knowing your room before you use humor · storytelling as the key to retention.

Guest advice: "Own the room. Know the room." Michael's guiding principle for using humor as a leader, learned from a mentor years ago.

Standout quotes:

• "I am copying and pasting, copying and pasting now. I'm a machine now. And that's not what we were built for... We were built for critical thinking. Emotions... And empathy." —Michael Earls
• "It doesn't have a heart. It's like a tin man." —Kate Davis, on AI and empathy

Connect with Michael Earls:

https://www.michaelearls.com/books/finding-direction-in-the-age-of-ai/

Finding Direction in the Age of AI
Wired for Purpose
The Digital Compass

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

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

Imagine a trolley hurtling down the tracks toward five people. You can pull a lever and divert it — but there's one person on the side track too. Most people pull the lever. And according to Ron Sosa, that's exactly how most workplaces are built: systems designed for the majority, with everyone else quietly getting run over. In this episode of Humor in the C Suite, Kate Davis sits down with Ron to talk about what it really costs to lead while masking, why humor is one of the most powerful tools for self-advocacy, and what becomes possible when leaders are finally given permission to lead as themselves.

Key Topics Covered

Ron and Kate explore the Trolley Scenario as a framework for understanding how workplace systems are designed — and who they leave behind. They dig into what masking actually costs neurodivergent leaders: the identity erosion, the accelerated burnout, the exhaustion of contorting yourself to meet an expectation that was never built with you in mind. Ron talks about how humor functions as a genuine tool for self-advocacy — not self-deprecation, but the ability to laugh at yourself in a way that makes the hard stuff lighter and the conversations easier. They cover the RISE framework, values-based leadership, and why Ron always starts coaching with personal values rather than professional ones. Kate shares her own experience with ADHD and anxiety, and Ron drops a stat that stops her mid-conversation: neurodivergent children receive an average of 20,000 more corrective comments than their neurotypical peers before the age of ten — and what that does to a person's relationship with humor, validation, and people-pleasing

Standout Quotes

"The ability to laugh at yourself makes the ability to advocate for yourself less heavy." — Ron Sosa

"Nobody is truly toxic. People just have unmet needs they don't know how to express — or needs we don't know how to meet." — Ron Sosa

"You conform to society, put on the leadership mask, and everything becomes heavier. You erode your own identity — and then you burn out faster." — Ron Sosa

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