Dilemma: I swore I’d never be like my old bosses, but now I’m not so sure

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June 25, 2025 • 13 mins

This week’s dilemma:

“I don’t want to give up on being the kind of boss I believe in. But I also don’t want to feel like a mug.”

In this minisode, we respond to a long-time leader wrestling with a modern challenge: how to hold people accountable without falling back on outdated, authoritarian styles of leadership.

Peter has spent two decades leading with clarity, compassion, and care. But lately, with shifting expectations, missed deadlines, and a whole lot of ambiguity, he’s starting to question whether he’s being too soft, or just trying to lead in a system that hasn’t caught up yet.

If you’ve ever tried to lead with integrity but felt tempted to “lay down the law,” this one’s for you.

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We’re answering real-life listener dilemmas all season long. Send yours to dilemma@thisisworkwell.com - anonymous, always.

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