The Question Challenge - Asking


The Question Challenge - Asking

To ask is to lead.

When my son was three years old, our conversations went like this.

Him: "Da-aaaa-aad... what's this called about?" he asks pointing at some frozen zucchini.

Me: "That's zucchini."

Him: "Why?"

Me: "Uhh, it was going off so I froze it."

Him: "Why Dad?"

Me: "I've heard it's good in smoothies."

Him: "Why?"

Me: "Apparently it makes them creamy.

Him: "... Why?"

Me: "I don't really know. Can you pass me that glass?"


I might be the adult, but who was the leader in that conversation?


How many questions do you ask every day?

On average, children ask 40,000 questions between the ages of 2 and 5. Sometimes it felt like my son intended to double that number.

But something happens as we grow older. Many of us learn to hide our questions. We're still curious, but we think:

  • I don't want to waste people's time; I'll just stay quiet.
  • I don't want to look stupid; best to keep my mouth shut.
  • I don't want to create chaos; I won't challenge them on that.

And then what happens?

We waste time on stuff that doesn't matter. People do stupid things. And our organisation exists in a constant state of looming chaos. The exact opposite of what we were aiming for.

The real leaders in your organisation are the ones asking curious questions and challenging the status quo. It's the fastest and easiest way to improve performance, increase engagement and get better outcomes.

But how do we ask without coming across as stupid or annoying?


One rule for asking better questions

If you forced me to give you one rule for asking better questions, it would be this:

Ask questions that start with "what" or "how" and avoid questions that start with "why" or "did".


What's wrong with "Why..." questions, you ask?

It's almost impossible to ask a question that starts with "Why..." without sounding like you're blaming somebody.

Why did you do that? Why DID you do that? WHY did you do that? Why did you do THAT?

No matter where we put the emphasis, it sounds like you're saying "You shouldn't have done that you eejit!"


What about "Did..." questions?

Questions that start with "Did..." or "Do you..." or "Have you..." aren't questions. They're suggestions, disguised as questions.

Did you speak to your General Manager? (You really mean: "You ought to have spoken to your General Manager.")

Have you been using AI to edit your reports? (You really mean: "I can tell you've been using AI to edit your reports.")

Those suggestions and observations are fine... but they're not questions. They're not going to generate new insights.


But how do we get underneath the surface if we can't ask "Why...?"

We use questions that start with "What..." or "How...".

Instead of "Why did you do that?", ask "What was going on around you?" or "What thoughts were running through your head?"

Instead of the eyerolling "Why would I do that?" try "How do you see that playing out?" or "What do you think the benefits will be?"

This might sound like a small tweak, but it can have a big impact.

But only if we then create the space for the answers to emerge. And that's the focus of our final email next week.

Until then, ask "what" or "how" questions, and see how people respond. I'd love to hear how you get on.

Go well,

Paul