How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)
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What powerful question does Jerry ask to spark self‑awareness?
We're socialized to bullshit not only ourselves, but everybody else. Especially in the entrepreneurial community. 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. 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 Wanna create a high functioning team? Do your work. And it starts with the person who has the most power in you.
Today, my guest is Jerry Colonna.
How does Jerry’s equation (practical skills + radical self‑inquiry + shared experiences) create better leaders?
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 JP Morgan Chase and is the author of two books. 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. 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 on your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you now get a year free of linear superhuman notion perplexity and granola. Check it out at lenny's newsletter.com and click bundle. With that, I bring you Jerry Colonna. This episode is brought to you by EPO.
Why do teams fail even when talent and strategy are present?
EPO is a next generation A B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Epo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And Epo helps you increase experimentation velocity. Velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more, with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that.
Helps you avoid annoying, prolonged analytic cycles. Epo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A-B testing flywheel. Epo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Epo at getepo.com/slash Lenny and 10x your experiment velocity. That's geteppo.com. dot com slash lenny This episode is brought to you by Content Square, the analytics platform that helps companies build better digital experiences. Ever wonder why customers drop off before converting?
How does busyness hide deeper issues of self‑worth?
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Chapters
8 chapters
1
What powerful question does Jerry ask to spark self‑awareness?
0:00–0:51
2
How does Jerry’s equation (practical skills + radical self‑inquiry + shared experiences) create better leaders?
0:51–2:07
3
Why do teams fail even when talent and strategy are present?
2:07–3:32
4
How does busyness hide deeper issues of self‑worth?
3:32–4:45
5
What is the role of radical self‑inquiry in uncovering unconscious patterns?
4:45–5:50
6
How can shared experiences and community strengthen leadership resilience?
5:50–6:45
7
Why can a growth‑mindset become a fixed‑mindset trap?
6:45–7:39
8
How should leaders navigate the unsettling rise of AI and its impact on humanity?
7:39–1:22:46
Speakers
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