Akeel JabberInvestment Director, Horizen Capital · Investor, Entrepreneur and Petroleum Engineer

Overcoming People Pleasing in Leadership

2 May 2026 · 1 min

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In this segment of the YouTube video "Overcoming People Pleasing in Leadership," the speaker reflects on a piece of advice he wishes he had known earlier in his career. He identifies a tendency toward people‑pleasing and the need to be liked, which becomes increasingly problematic as one ascends into leadership roles. The core recommendation is to develop the skill of having uncomfortable conversations, supported by a deliberate framework, rather than avoiding conflict to maintain popularity. He emphasizes that this skill is not about being harsh, but about addressing difficult topics proactively, and notes that mastering it earlier would have benefited him in several past situations.

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What's one piece of advice, you know, you wish you had known, Matt? And if you can go back, you would tell your, say, 25-year-old self? Yeah, I'll tell you exactly what it is. It goes back to about having uncomfortable conversations. Left unchecked, I can sometimes want to be a people pleaser. I have like this need to be liked, you know, and the farther you get in leadership, the less you can have a space for that. It doesn't mean that you walk around being an asshole to everybody, obviously, you know, but when there's an uncomfortable conversation to be had, you have to have it and you have to have a framework for having it and get good at having it. It's a skill to be built. And, you know, I think I've got that skill now, but I would— I can think of a few situations where it would have served me if I had built it a little bit more deliberately, a little bit earlier. So that's probably where I'd be with that one.