When Was the Last Time You Questioned Your Own Questions?

When Was the Last Time You Questioned Your Own Questions?

You’re a leader. Which means people come to you for answers. For reassurance. For direction. Your diary’s full. Your head’s even fuller. Everyone wants a piece of your focus — and most days, it feels like you’re juggling clarity with chaos.

But here’s the bit that’s easy to forget: If you’re not asking yourself the right questions, how can you help anyone else?

It’s like they say on planes — fit your own oxygen mask first, before helping others. Not just because it sounds wise. Because without it, you’re no good to anyone.

Self-leadership isn’t selfish — it’s how you stay able to support others.

Real change starts with better questions. Not just for others. For you. The quiet ones. The inner ones. The ones no one else hears but shape everything you do.

There are three levels. Each one matters.

  1. With yourself
  2. One-to-one
  3. In groups

Let’s start at the beginning.


Level 1: The Conversation You’re Having with Yourself (yes, that one you are doing right now).

This is the one no one else hears. But it shapes everything.

That quiet, constant voice narrating your day — are the questions it’s asking helping you… or holding you back?

Too often, self-talk sounds like:

  • Why can’t I figure this out?
  • What if this goes wrong?
  • Am I really up to this?

But what if you shifted those questions — even slightly?

Consider:

  • How could I approach this differently?
  • What could I possibly learn?
  • What would success look like if this all went right?

You don’t need to be endlessly positive. Just endlessly curious. It’s a subtle shift — but it changes the whole direction of your day.

You’ve already got the tools; you use them every day. But the quality of your questions decides how powerful they become.


Level 2: One-to-One Conversations (the heart of how you lead)

These are the conversations that build trust. That shape culture in the small moments. They can feel routine — a quick check-in, a passing chat in a corridor— but they hold real power.

And the questions you ask in these moments? They really matter.

Move from:

  • “What’s wrong?” to What change would you like to see — and what part could you play in making it?”
  • “Do you need help?” to “What support would be most useful right now?”
  • “What’s the update?” to What decision do you feel closer to making? – What is still uncertain?”

These kinds of questions create space. They tell the other person: You’ve got this — I’m just here to help unlock it.


Level 3: Group Conversations (where culture gets made)

This is where the tone of your team gets set. In meetings, briefings, away days — wherever people gather, consciously or not, they’re asking themselves: Do I belong here? Do I have a voice?

And the questions you ask as a leader will either open that space… or quietly close it.

Instead of defaulting to updates and to-do lists, explore:

  • “What haven’t we considered yet?”
  • “What assumptions are we working with?”
  • “What’s the one thing we’ve not yet questioned?”

Better questions don’t just lead to better answers. They lead to better thinking. And better thinking leads to better outcomes.


And So...

Leadership isn’t about always knowing what to say. It’s about being curious enough to ask the things that matter. To yourself. To others. To your team.

So, put your oxygen mask on first.

Then ask:

·        What kind of leader do I choose to be today?

·        Which conversation have I been avoiding — and why?

·        What powerful question could unlock fresh thinking — in me, or in someone else?

Change starts with a question. Make it a good one.

I’m curious — did any of these questions make you pause for thought? If so, let’s dive deeper together. I’m always open for a chat that sparks new insights and fresh perspectives.

What’s been on your mind lately? Let’s swap ideas.

wayne.bird@gomadthinking.com

www.gomadthinking.com

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