Insights

How to get honest feedback when you’re the boss

The problem is structural, and no amount of warmth fixes it on its own.

Leo Judkins, Founder, The iGaming Leader  ·  September 2026

Most advice on this topic tells you to "build a culture of trust" or "create psychological safety," as if the problem were your tone in meetings. It isn’t. The problem is structural, and no amount of warmth fixes it on its own.

Why internal hierarchy makes this genuinely hard

Everyone who works for you has a stake in what they tell you. Their compensation, their progression, their title, what’s riding on this for their family. That’s not a flaw in your team, it’s just what it means to have a career that depends, in part, on what you think of them.

So even a genuinely direct team has a ceiling. They’ll tell you when they think you’re wrong on strategy or execution. They won’t tell you about the peer at their own level who’s underperforming. They won’t tell you they’re out of their depth. They won’t tell you the decision that’s still unformed in their own head, because saying it out loud makes it something that has to be actioned. As long as it stays quiet, nothing needs to happen.

Asking your team to just "be more honest" doesn’t change any of that. The incentives are still exactly where they were.

What actually works instead

Separate the relationship from the stakes. The most reliable honest feedback doesn’t come from inside your reporting line at all. It comes from people who have nothing to gain or lose from how you receive what they say, because they don’t work for you and never will.

Ask for the thing they’d never volunteer. Instead of "any feedback for me," which invites a safe, generic answer, ask directly: what have you been thinking about a decision I’ve made, that you haven’t said out loud yet. That question specifically targets the category people default to withholding.

Build a standing structure, not a one-off request. A single "tell me honestly" conversation rarely produces real honesty, because the person you’re asking is still weighing the same stakes they always weigh. A recurring structure, with people outside your organisation, where challenge is the explicit purpose of the room, changes what people feel safe saying, because the cost of saying it has actually changed, not just the invitation to say it.

Get comfortable with stories over opinions. The most useful honest feedback rarely sounds like an opinion about you. It sounds like someone else’s story: here’s what I did in a similar situation, here’s what went wrong, here’s what I’d do differently now. That format sidesteps a lot of the awkwardness of direct criticism, while still landing the point.

Why this can’t be solved inside your own business

Even with the best intentions, and the most genuinely direct team you could hire, the honesty gap doesn’t fully close, because it isn’t really about culture. It’s about incentives that exist as long as someone’s career depends on your judgement of them. That’s true at every company, run by every kind of leader, regardless of how approachable they are.

Which means the fix has to sit, at least partly, outside the business. People with no stake in your decision, no reporting line to protect, and their own version of the exact call you’re wrestling with.

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