

Jerry Colonna: The Questions Every Leader Needs to Ask Themselves
8 snips Aug 12, 2025
In this engaging discussion, Jerry Colonna, CEO of Reboot.io and executive leadership coach, dives into the transformative power of radical self-inquiry. He discusses challenging questions leaders should ask themselves to foster growth and humility. Jerry shares his journey from a financial leader to a purpose-driven coach, emphasizing the importance of empathy and active listening in both leadership and parenthood. He also sheds light on the balance between coaching and therapy, advocating for a leadership style rooted in values and community.
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Collapse That Triggered Change
- After a long run of success Jerry collapsed at home and heard his daughter think he was dying.
- That incident pushed him into therapy and radical life change.
Lemon Drops As Safety Symbol
- Jerry Colonna's grandfather kept a tin of lemon drops that symbolized plenty and safety.
- He chased that feeling his whole life, driving relentless striving until a collapse.
Books That Rerouted A Career
- Jerry went to Canyon Ranch and read three life-changing books on the flight.
- Those books rerouted him toward empathy and a coaching career.