April 2026
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    I just stepped into a new leadership role and could use some perspective.

    I’m [30M] and most of the team I manage is around my age or younger. A few of them are technically “executives” as well, so it’s not a traditional hierarchy. I was brought in by the owner’s son, who’s pretty forward-thinking, to help build out a newer side of the business. I have about 5 years of experience in this space and a background in scaling businesses; but always under founders, partners, or senior leadership. This is the first time I’m really the one expected to lead.

    On paper, I know I can do the job. But in practice, I’m definitely feeling some imposter syndrome… especially managing people who feel more like peers than direct reports.

    I’ve always been a pretty laid-back, collaborative person. That’s worked well for me so far, but now I’m realizing I need to balance being approachable with actually having authority and setting direction. I don’t want to become overly rigid or disconnected, but I also don’t want to come across as passive or unclear.

    I came in with some credibility and trust, which helps. But now I’m trying to figure out how to:

    1. Start setting clearer expectations and direction without overstepping

    2. Earn respect while still being relatable

    3. Actually “lead” instead of just contributing ideas and hoping people follow

    I want to be the kind of leader people respect and enjoy working with, not someone they feel distant from or micromanaged by.

    For those who’ve been in a similar spot, especially managing peers or stepping into leadership for the first time, what books helped you make that shift?

    by lookingbullish

    1 Comment

    1. Checking out Managing Oneself by Peter Drucker if you haven’t already. It’s a classic, but also highly introspective, which it sounds like you might be. 🖤

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