How have I been complicit in creating the conditions I say I don’t want?

Jerry Colonna, co-founder and CEO of Reboot, former venture capitalist turned executive coach, and author of Reboot and Reunion, discusses how leaders can examine their own patterns instead of blaming circumstances. The conversation covers radical self-inquiry, the danger of tying self-worth to achievement, legacy, how dysfunction in teams often traces back to the most powerful person, and how AI and growth mindset fit into this work.

01Key learnings

• Ask how you have been complicit, not responsible, in creating the conditions you say you don't want; this evokes personal agency without self-blame.
• Use radical self-inquiry to examine what you claim to want versus what you actually feel, such as saying you dislike busyness while feeling unsettled when your calendar is empty.
• Notice whether your drive comes from proving your worth; separate the enjoyment of the work from the need to feel like somebody.
• Regularly ask yourself: what am I not saying that I need to say, what am I saying that isn't being heard, and what is being said that I'm not hearing.
• Share hard truths in trusted circles of peers, coaches, or therapists, since much of what entrepreneurs call success is a performance that hides real problems.
• Hold a growth mindset loosely; once it becomes a fixed rule about how you must be, it turns into ego-driven attachment and suffering.
• Teams often replay the leader's unresolved family patterns, so the person with the most power has the greatest responsibility to do their own inner work.
• If you want a scaled leadership team, tolerate teammates making decisions you disagree with, otherwise you cannot build people who decide without you.

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.