Stupid Questions: Learn to Embrace Them

“There’s no such thing as stupid questions.”

We’ve all heard that phrase espoused by leaders, project managers, consultants, facilitators and trainers. We’ve probably used it ourselves upon occasion. It’s the thing you say to fill the awkward silence… because you know that what you just shared is new and a little bit complicated, and you assume no-body wants to be seen as stupid by their peers (or their boss).

“I can guarantee if you have a question, somebody else will have the same question and be grateful you asked it” they say… as though that’s the inducement you needed to build the courage to look a bit slow in front of your workmates…

And let’s face it, when we’ve been in that room, we’ve all groaned (hopefully inwardly) at the actual stupidness of the eventual question that gets asked.

Today though, I’m going to try and convince you to embrace stupid questions. Not because it helps the people in your audience – whether clients, or peers, or your staff – but because it helps you.

Stupid Questions

What are stupid questions?

This might seem like a stupid question. So let me tell you a story.

My school-age son is enrolled in a before-school programme. There’s also an after-school programme offered by the same provider, but it has a massive waiting list. At the end of each school term, we have the opportunity to supplicate ourselves to be on the waitlist… again… in the hope – futile though it may be – that our son has progressed sufficiently high on that list that we might get a place.

Each term, when we do this, the email says “your child is automatically granted the same slot he or she had this term. If you have requested additional spaces, you will be wait-listed. We will notify you if that space becomes available.

The day before term starts, my anxiety about not having heard anything finally gets the better of me, and I contact the programme “just to check” that Mr 5 in, in fact, on their list, and that he hasn’t miraculously been granted an additional slot.

Without checking any actual list, I’m made to feel like an idiot for not properly reading an email I received two months ago.

This morning (after asking this question) I realised three things:

  • First, it’s entirely possible that I am an idiot. I’m up for that, if the evidence points in that direction.
  • Second, “Don’t call us, we’ll call you” is never a good approach, because the risk of administrative error and the absence of any potentially corrective dialogue, is a recipe for disaster… showing up at 7.30 am to be turned away and having to fill an hour until the acceptable drop-off time at school simply isn’t a workable worst-case scenario for me.
  • Third, what wonderful rich feedback that question is, to someone who is capable of seeing it that way, and open to acting on it! Embrace it! Use it as impetus to improve whatever your thing is!

You see, the power of Stupid Questions isn’t in the answer to them, or in the courage of those who decide to ask them. The power of Stupid Questions is in the opportunity they present you with, to alter your approach so that that particular stupid question isn’t needed again in the future.

Because the people asking the questions aren’t actually stupid. You are at fault. Not in a blamey way, just in a “you haven’t communicated effectively” way.

How do I embrace stupid questions?

De-emphasise the asker

Well, you still need to ask for them. But you need to shift the focus of the asking. Implying that the person asking the question needs to be brave to ask them, or is doing their colleagues a big favour by asking, is placing all the emphasis on the person asking (or potentially asking). Instead, put the focus on the person seeking the questions: “I know I haven’t explained this as well as I could have – what didn’t make sense? What are you left puzzled by?” Make it about you and your presentation of the information – which, let’s face it, can always be improved.

Watch how you respond

When you hear the question, you almost certainly have an immediate reaction to it. It probably starts with ‘but’:

  • But I covered this already
  • But I sent you this information in an email
  • But I thought that was the clearest part of my presentation
  • But… But… But…

“But” is a word you should try and banish from your vocabulary. Replace it with AND. The sentence still works, but it leaves space for multiple perspectives, and diminishes defensiveness for both parties.

Defensiveness is your ego’s way of trying to protect itself from the idea that you aren’t as wonderful as it thinks you are… or worse, that you aren’t great, but everyone else is worse.

Engage with the lesson

Instead, try and enthusiastically embrace the opportunity to learn from what the asker has shared with you. Especially if you get the same or similar questions often.

In my case, a programme administrator for a before/after school programme, probably knows that parents don’t want any uncertainty about whether their kids are in or out… waitlisted, or successfully slotted… In this case, the tradeoff is the lesser hassle of not sending out 100-odd tailored emails (though a template would probably suffice).

Communication is one of those things that we assume is more effective than it actually is, because we know what we were thinking and cannot know how it was received.

So make it your mission to embrace stupid questions. They are rich sources of intelligence for you – real-time feedback on how you are performing. Don’t let that go to waste!


If you have stupid – and not so stupid – questions about leadership, you might like to sign up for our free virtual coaching newsletter. It’s lovely!

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