What’s the most dangerous thing an executive can hear from their team? “Everything’s fine.”

As a leader, questions like “How can I support you?” and “What’s one thing I/we could do differently?” are meant to build trust and shape culture.

But here’s the part most execs miss: You won’t get a real answer the first time. Or maybe even the second.

Why? Because most employees and teams don’t know—yet—if they can trust the question.

They’re wondering:

  • Do you really want to know?
  • Will you actually do something about it?
  • If the answer is anything other than “great!” will it be held against me?

When I’m working with executive teams and they collectively voice frustrations about wanting to truly understand how their employees are doing but never getting straight answers, I always tell them:

Ask once. Then ask again, and again.

Eventually, the question is normalized. The risk is lowered. They’ll start to believe you really want to know, and they’ll start to answer.

But that only happens when your team sees that you mean it—not just once, but every time. You show that you mean it when you listen with care. Respond with intention. Act on what they tell you (or explain why you won’t). And make it safe to be honest, even when the answers are hard to hear.

The executives who master this create teams that actually tell them what’s broken before it becomes a crisis.

The ones who don’t? They’re always the last to know when things go sideways.

Which leader are you choosing to be?

PS – I’m not talking about that engagement survey you’re so attached to. I’m talking about conversations. But if you do that engagement survey, you’d better take action on the results. If you don’t, and you keep doing the survey and nothing happens, you will absolutely lose their trust that you care what they think.


Looking to increase the cohesion, trust, and impact of your leadership team? Reach out and let’s discuss The Compass Team Experience and how I can help.

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