Going Gun-Shy as a New Leader: Jesse Jackson on "We Tried That, It Didn't Work" episode artwork

EPISODE · May 4, 2026 · 49 MIN

Going Gun-Shy as a New Leader: Jesse Jackson on "We Tried That, It Didn't Work"

from My Favorite Mistake: Learning Without Blame in Business and Leadership · host Mark Graban

Jesse Jackson, contact center leader and host of Set Lusting Bruce, joins Mark Graban to share his favorite mistake: going gun-shy as a new leader when veterans push back with "we tried that, it didn't work." Jesse explains why that deference cost him his best ideas, and how a Harry Chapin story about "two kinds of tired" reshaped the way he leads. Episode page with video, links, and more We get into the real cost of staying quiet when you're new, the difference between listening to your team and being silenced by them, and the Aaron Sorkin line about surrounding yourself with smart people who disagree with you. Jesse also shares a cautionary tale about volunteering for a role he wasn't ready for, and what he changed about how he chooses opportunities now. The conversation moves into what psychological safety actually looks like day to day - treating new ideas as honest experiments rather than ego defense, and making sure team members feel heard even when their advice isn't taken. We close with a stretch of podcasting craft (forgetting to hit record, scheduling buffers, the value of embracing tangents) plus tangents of our own on Bruce Springsteen, the misunderstood patriotism of "Born in the U.S.A.," and Spinal Tap. If you've ever walked into a new role with ideas and quietly let them die in the face of "that won't work here," this episode will give you a sharper way to think about when to push and when to listen.

Episode metadata supplied by the publisher feed · Published May 4, 2026

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Jesse Jackson, contact center leader and host of Set Lusting Bruce, on the mistake of going gun-shy as a new leader when veterans push back with ”we tried that, it didn’t work.” A practical conversation about speaking up, psychological safety, and when to trust your own judgment.

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Going Gun-Shy as a New Leader: Jesse Jackson on "We Tried That, It Didn't Work"

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This episode was published on May 4, 2026.

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