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Jerry Colonna

Episode #145

Co-founder & CEO

Reboot

🚀Career & Leadership👥Team & Culture

📝Full Transcript

11,717 words
Jerry Colonna (00:00:00): We're socialized to bullshit not only ourselves, but everybody else, especially in the entrepreneurial community. All our companies are moving up into the right. Every product is working. We don't really have any problems because we're crushing it, and that's just a lie. The question that I often ask is how have I been complicit in creating the conditions I say I don't want. The purpose of this question is actually to evoke your own agency. A perfect example of that would be, I say I don't want to feel busy all the time, but the truth of the matter is I feel really unnerved and disconcerted if my agenda isn't jam-packed. So if you want to create a high-functioning team, do your work, and it starts with the person who has the most power. Lenny Rachitsky (00:00:49): Today, my guest is Jerry Colonna. Jerry is one of the most well-known and respected executive coaches in the world. He's co-founder and CEO of Reboot, an executive and leadership development firm grounded in the belief that better humans make better leaders. Prior to coaching, Jerry co-founded Flatiron Partners with Fred Wilson, which ended up being one of the most successful early-stage investment funds in the world. He's also a partner at JPMorgan Chase and the author of two books, Reboot and Reunion. As you might expect, this ended up being a very real and very open conversation about being busy and self-inquiry and the dangers of a growth mindset and the reasons that leaders and teams most often fail, and it's not what you think. Also, we talk about a very simple equation that Jerry and his team use to cultivate great leaders. (00:01:37): This is an episode that everybody should listen to and spend time with. It'll make you a better person, a better partner, and a better leader. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you now get a year free of Li...

💡 Key Takeaways

  • 1The 'Complicity Question' helps leaders regain agency by identifying how they contribute to problems they complain about.
  • 2True leadership resilience requires a combination of practical skills, self-inquiry, and shared experiences.
  • 3Busyness is often a trauma response or a way to quiet the inner imposter syndrome voice.
  • 4Team dysfunction is often a fractal of the leader's own unresolved psychological baggage.
  • 5Success and money do not solve internal feelings of insecurity; only decoupling self-worth from outcome does.

📚Methodologies (3)

🚀 Career & Leadership

A psychological tool to shift from blame to agency. By asking how one is complicit (like an accomplice, not necessarily responsible/guilty) in creating unwanted conditions, leaders uncover the hidden benefits or 'delusions' driving their behaviors.

Core Principles

  • 1.Ask the core question: 'How have I been complicit in creating the conditions I say I don't want?'
  • 2.Distinguish 'Complicity' from 'Responsibility': You are the getaway driver, not necessarily the bank robber.
  • 3.Identify the 'Hidden Benefit': What psychological need is being met by this bad situation? (e.g., being busy = feeling important/safe).
  • +1 more...

"The purpose of this question is actually to evoke your own agency. A perfect example of that would be, I say I don't want to feel busy all the time, but the truth of the matter is I feel really unnerved... if my agenda isn't jam-packed."

#complicity#inquiry#career
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👥 Team & Culture

A holistic formula defining sustainable leadership. It argues that practical skills must be combined with internal psychological work and community support to achieve not just better performance, but personal resilience.

Core Principles

  • 1.Variable 1: Practical Skills (The 'How' - Strategy, Product, Finance).
  • 2.Variable 2: Radical Self-Inquiry (The 'Why' - Unpacking motivations, fears, and history).
  • 3.Variable 3: Shared Experiences (The 'Who' - Vulnerable peer support/Circles to combat isolation).
  • +2 more...

"I get you want to be a great CEO... but what I really care about is you not killing yourself in the process."

#reboot#leadership#equation
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👥 Team & Culture

A set of four diagnostic questions designed to pierce through the 'bullshit' of corporate politeness and uncover the root causes of misalignment or resentment.

Core Principles

  • 1.Q1: What am I not saying that I need to say? (Identifying withheld truth/conflict avoidance).
  • 2.Q2: What am I saying that's not being heard? (Identifying communication gaps/ineffectiveness).
  • 3.Q3: What is being said that I'm not hearing? (Identifying listening filters/confirmation bias).
  • +2 more...

"You know you're in the radical self-inquiry zone when the questions take your breath away."

#communication#alignment#matrix
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