The question you didn't ask

Can you think of a time when you chose not to ask a question at work for fear of looking silly or not wanting to bother someone?

By avoiding asking clarifying questions, we run the risk of miscommunication, conflict and potentially longer-term resentment. Here's how this plays out in real situations:

Take a manager of a small group of freelancers. They want to find out whether they are available for an upcoming project. One of the freelancers doesn't reply. The manager hesitates. Should they follow up? It has been a few weeks since their previous interaction. But they don't want to seem pushy or, even worse, like they're nagging. Surely if they were that keen, they would have replied by now… So they assume the freelancer isn't interested or available, and they staff the project with someone else.

Later, the freelancer hears from a colleague and is baffled that they were overlooked for the project. They check their inbox. No, there was definitely no follow-up. They feel sidelined, confused why they never got that check-in email. The trust erodes, on both sides, and the company loses a good freelancer because of a conversation that never happened.

How could that situation have been avoided? You could argue that the freelancer should have responded sooner. Or the manager could have asked a simple clarifying question in a follow-up email. The truth is, both hesitated at a small moment of potential awkwardness and that led to a breakdown in communication.

What if the manager felt comfortable sending that casual follow-up? What if the freelancer knew how to signal they needed more time without them feeling needy? The confidence in these situations come from practiced behaviours.

In my training sessions, I create scenarios just like this one. Participants practice the actual moment of discomfort, such as sending that follow-up, asking for clarification, and admitting they don't understand something. We do this in a low-stakes environment where there's nothing to lose. We use techniques that I’ve learnt from improv theatre to make the awkwardness feel manageable, even playful. It's surprising how much easier the real conversation becomes once you've fumbled through the uncomfortable version first.

We realise the questions we're often afraid to ask aren’t silly at all. They are the questions that stop everything from unravelling.