A Story
I ran a workshop this morning for a room of senior managers and gave them a simple scenario:
One of your employees is standing at your door and wants some support. A colleague named John had agreed to finish three things last week, but he blew them off. He didn’t even give her a heads-up, and now the project is a week behind schedule.
I asked the group what they might say or what questions they would have for her.
Here’s what they came up with:
- Was there any follow-up?
- Did you ask him why it didn’t get done?
- When was the deadline?
- Did he understand the assignment?
- Why didn’t you make sure he was doing it?
Can you see a pattern in these questions? I wrote them all on a whiteboard and asked the group to look for the pattern. Nobody saw it right away.
Then someone jumped in. None of the questions were actions; they were diagnoses. And every single one of them pointed at the woman standing in the doorway, not at John, the guy who actually dropped the ball.
No one in my workshop meant to put her on trial. But asking, “Did you follow up?” and “Why didn’t you? sent a strong subliminal signal that something here is your fault, and I’m going to find out what it was.
An Insight
I think a lot of us stumble into questions like these without realizing what they actually do.
As leaders, we think our job is to problem-solve, so when someone brings us a problem, we jump on that bandwagon and start investigating. We ask what happened, whose fault it is, and what the timeline is. These questions make us feel responsible. We feel like we are leading, when all we are doing is spinning. Last week I wrote about how we often move so fast we end up feeling like hamsters running on a hamster wheel, and this is another example of that. We are so compelled to solve problems, so we end up accidentally accusing people of wrongdoing without ever intending to.
We need to realize that investigating and leading aren’t the same thing, and the person standing in front of you can feel the difference immediately. A “why” question, even asked gently, sounds like you’re building a case. A “did-you” question sounds like you already suspect the answer is no. Neither one makes a person want to open up to you, and neither one is an effective way to have a difficult conversation at work.
One of my favorite organizational psychologists, Edgar Schein wrote an excellent book on this very subject, and I’d encourage you to check it out. He called it the discipline of humble inquiry and defined it as: asking a question you genuinely don’t know the answer to, instead of one built to confirm what you already suspect. Most leaders default to diagnosing because it feels efficient. Schein’s point was that the habit accidentally wears down the very trust it’s trying to protect.
That’s exactly what happened on the whiteboard this morning. Every question they came up with was reasonable on its own. But every question also had the potential to make the woman feel like she needed a lawyer. Every question implied that I don’t trust you!
A Subtle Shift
So here is the shift I’m proposing this week, and I have to admit that this one is pretty subtle:
Trade why questions for what questions.
Instead of asking “Why didn’t you follow up,” ask “What are you learning from this situation?” Instead of asking “Why did he decide not to do it,” try “What do you think we should do about it?” Instead of jumping straight to a fix, ask “What can I do to help?”
Two things happen when you make this shift.
- You stop sounding like you’re building a case and you start sounding curious.
- The other person usually starts diagnosing the problem themselves, and they feel empowered.
And here is the magic. When you ask someone a forward-looking question, they’ll often walk themselves to the same conclusion you would have handed them anyway. Except now it’s theirs, not yours, and that is powerful!
So here’s a gentle suggestion.
The next time you feel a difficult conversation coming on, catch yourself before the “why” or the “did-you” leaves your mouth. Ask one question that starts with what or how instead, then stop talking.
By the end of the session this morning, I’m pretty sure everyone understood this subtle shift, and I hope this helps you see it too.
Difficult conversations at work rarely get easier because you finally have the right answer. They get easier the moment you stop needing one so fast.

