Lenny Distilled

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

May 08, 2025

Featuring: Jerry Colonna (CEO and Co-founder, Reboot)

4 quotes · 3 insights

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Everything changes, so appreciate what you have now

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.
Jerry ColonnaCEO and Co-founder, Reboot 00:00:00

Listen deeply - win-wins exist when you dig deeper

What am I not saying that I need to say? What am I saying that's not being heard? And what's being said that I'm not hearing?
Jerry ColonnaCEO and Co-founder, Reboot 00:23:40

Team dysfunction starts with leadership

If you want to create a high-functioning team, do your work, and it starts with the person who has the most power.
Jerry ColonnaCEO and Co-founder, Reboot 00:00:00
Who hired them? How does it make you feel when they make a decision that you disagree with? You want to build a scaled leadership team, you have to be willing to have them make boneheaded decisions.
Jerry ColonnaCEO and Co-founder, Reboot 17:28

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