Ever met a leader so “humble” they practically tattoo it on their LinkedIn headline? In this episode of The Jest Business, Paddy and I dive into the hilarious—and sometimes cringey—world of humility in leadership. We roleplay arrogant CEOs, swap LinkedIn horror stories, and break down why real humility has nothing to do with saying “humbled.” Inspired by a recent business event that left us blinking at the lack of self-awareness, we ask: can you be ambitious and modest? Come for the Gandhi impression, stay for the BS (Benson Style).

Discussion Topics: This Is NOT What Humility Looks Like

• Is humility in leadership just as rare as privacy on social media?
• Four CEOs. One panel. Zero humility. You won’t believe what they said.
• A leadership concept you’ve probably never heard of—but should.
• The ‘Southpaw Maneuver’ explained… and no, it’s not boxing advice.
• Gandhi goes corporate. What if Bapu was a CEO today?
• You know Jack Welch. But the real hero? You’ve probably never heard of him.
• What truly happens when the “great” leaders leave?
• The CEO who tattooed his mantra on people’s minds (figuratively… we hope).
• “Talk the walk”? A masterclass in humblebragging.
• The most un-humble “humble” feedback you’ll ever hear.
• Why your LinkedIn “I’m humbled” post isn’t fooling anyone.
• Real humility vs. corporate cosplay—how to tell the difference.