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Lenny Rachitsky: recommendation

8 May 2025 Lenny's Podcast How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

“A big takeaway for me here, and it just keeps coming up and again and again, is if you're struggling as a leader, if your company's not working as well as you wanted to, if you're having a hard time with your team, going back to that equation, it's not about building more skills like public speaking skills or email skills, or I don't know, financial skills.”

— Lenny Rachitsky

Source trail

Everything needed to verify it.

Speaker
Lenny Rachitsky
Attribution
Verified speaker
Claim type
recommendation
Recorded
8 May 2025
Publisher
Lenny's Podcast

Transcript context

…One of the things to ask oneself is what draws me to this position in the first place? How have I been complicit, not responsible in creating the conditions I say I don't want. How have I benefited from the dysfunction that exists in this organization? And benefit is a funny word. It doesn't necessarily mean I'm making more money. It means, for example, a benefit might be, boy, this feels familiar. I always find myself working on teams that are dysfunctional in this way. What is there in that experience for me to learn? So that's one thing. You asked about the person who has power. You were using the word leader. I will talk about power, and you threw out, well, should they get a coach? Let's put it into larger context. Should you examine your life with radical self-inquiry? Yes. I would argue that the more power you have, the more moral responsibility you have to actually pause and figure out what it is that you're doing to be complicit in creating the conditions you say you don't want. To be a very quick example what I'm talking about. A couple of years ago, I was doing a talk at a venture firm's CEO portfolio summit, the portfolio company's CEO summit. And we're sitting in a room, and of course I'm walking around again with shoes off and whatever, and people are firing questions at me. And one woman says, "Well, I'm the CEO of this 15-person company, and I have a question for you. Why is it that nobody on my team can make a decision without me?" And I said, "Who hired them?" And she, "Well..." I said, "Okay, how does it make you feel when they make a decision that you disagree with?" She said, "I'm furious." "Well, how can you hire people whom you expect to make decisions without running them through you if you can't tolerate them making 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. And that's really, really hard, especially if we're "in founder mode" driving all the decisions. So that's your growth edge. We were talking about before about growth mindset. That's your growth edge. How can I be with the people in my life making boneheaded decisions about something that I care so much about and what is the best way for me to be in relationship about that? So much of this comes back to that question we started this with of just how are you complicit in creating the conditions you don't want? A big takeaway for me here, and it just keeps coming up and again and again, is if you're struggling as a leader, if your company's not working as well as you wanted to, if you're having a hard time with your team, going back to that equation, it's not about building more skills like public speaking skills or email skills, or I don't know, financial skills. It's self-awareness, radical self-inquiry, understanding what drives you, what makes you happy. Is that generally correct? Lenny, I was just going to say, you just made me so happy you saying what you just said. Yes. I've been coaching now, as I said for a couple of decades. Before that, I was a VC for 15, 17 years. What you just said is the wisdom of my 40 years as an adult. That's it. This is why radical self-inquiry is so damned important because it leads to a little bit less suffering and a lot more resilience.…

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