Jerry Colonna
Co-founder and CEO at Reboot
One of the most well-known executive coaches in the world, co-founder of Reboot and former co-founder of Flatiron Partners with Fred Wilson, author of Reboot and Reunion, known for his radical self-inquiry approach and the leadership equation of practical skills plus radical self-inquiry plus shared experiences equals enhanced leadership and resilience.
Dimension Profile
Key Themes
Episode Summary
Jerry Colonna shares his radical self-inquiry approach to executive coaching, centered on the question 'How have I been complicit in creating the conditions I say I don't want?' He introduces the leadership equation — practical skills plus radical self-inquiry plus shared experiences equals enhanced leadership and resilience — and argues that resilience, not performance, is what truly matters because too many successful people achieve everything and are still miserable. The conversation cuts through the socialized bullshit of entrepreneurial culture where everyone pretends they're crushing it.
Leadership Principles
- → How have I been complicit in creating the conditions I say I don't want? Complicit does not mean responsible — you're driving the getaway car, not sticking up the bank teller
- → Practical skills plus radical self-inquiry plus shared experiences equals enhanced leadership plus greater resilience — the resilience part is what really matters
- → We're socialized to bullshit ourselves — all our companies are moving up and to the right, every product is working, we're crushing it, and that's just a lie
Notable Quotes
"How have I been complicit in creating the conditions I say I don't want? Complicit does not mean responsible. Think of the word accomplice. You're driving the getaway car, you're not sticking up the bank teller."
— On his signature self-inquiry question for leaders
"We're socialized to bullshit not only ourselves, but everybody else. All our companies are moving up and to the right. Every product is working. We don't really have any problems because we're crushing it, and that's just a lie."
— On the pervasive dishonesty in entrepreneurial culture
"I get you want to be a great CEO. I get you want to be a great executive. But what I really care about is you not killing yourself in the process."
— On why resilience is the true purpose of leadership development
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