MSS #0135: How to Ask Better Questions – Unlocking Insight in Yourself and Others

MSS #0135: How to Ask Better Questions – Unlocking Insight in Yourself and Others

09 Aug, 2025

🕒Read time: 3.5 minutes
🚀 In a hurry? Skip to “9 Powerful Questions to Ask This Week” for a reduced reading time of 1.3 minutes.

It’s easy to rush to solve a problem far too early.

We often skip past the part that matters most — the questions.

This week is about slowing down, listening better and using questions that genuinely help people think.

Whether you’re leading a team, supporting a colleague, coaching someone, or sorting your own head out — the quality of your questions shapes the quality of your insight.

Why Questions Matter More Than Advice

Advice is tempting.

It feels helpful, efficient, generous.

But it often lands flat.

That’s because advice says: “I know the answer.”
A good question says: “You’ve probably got more of the answer than you realise — let’s find it together.”

Good questions don’t fix people.

They create space.
Space to reflect, not react.

To feel capable, not corrected.

The Wrong Kind of Questions

It’s easy to slip into questions that narrow things down instead of opening them up:

• “Why did you do it that way?”

• “Is this working or not?”

• “What’s wrong with you?” (often asked silently)

These questions lead to defence or shutdown — not insight.
They imply judgement, even when unintentional.

So, let’s work with a different approach.

Guidelines for Asking Better Questions

Whether it’s a conversation with yourself or someone else — these ideas help create space for clearer thinking and better answers:

1. Ask to Explore, Not to Diagnose

Curiosity changes the tone completely.

Instead of: “What’s wrong here?”
Try: “What’s feeling difficult right now?”

It softens the conversation, while still going somewhere useful.

2. Strip Out Implied Blame

Some questions sound like traps.

Instead of: “Why did you choose that approach?”
Try: “What influenced your decision at the time?”

This invites someone to explain, not defend.

3. Ask as if the Answer’s Already in Them

Try:

• “What do you already know about this?”

• “What have you already tried that helped even a little?”

This nudges people (and yourself) out of helplessness.

4. Go One Layer Down

Surface answers are often just that — surface.
Follow up with:

• “What else is going on?”

• “What’s underneath that?”

• “Is there something you haven’t said yet?”

That second layer is where the gold usually is.

5. Avoid Yes/No When You Want Insight

Binary questions limit the conversation.

Try:

• “What’s going well — and what’s frustrating?”

• “What parts feel clear, and which bits are messy?”

This helps people reflect in a more rounded way.

9 Powerful Questions to Ask This Week

For yourself. For someone you support. For a team conversation.

Use them with care and give time for the answers to surface.

1. What’s not being said here, that might matter?

2. What are we assuming that might not be true?

3. What would ‘better’ look like — for you?

4. What small shift could make this feel easier?

5. What’s the frustration really about?

6. What do you wish you could say right now?

7. What’s the kindest way you could respond to this?

8. What’s something you’ve avoided thinking about — that might help to face?

9. What would you ask a friend if they were in your shoes?

Good questions don’t demand instant answers.
They hang in the air. They open the door.

Summary

Clear, thoughtful questions are a powerful way to support insight — whether you’re speaking to someone else or just trying to think something through.

They create room for reflection, challenge with care and help move stuck conversations forward.

• Advice closes space. Questions open it.
• Avoid questions that sound like blame, even if well meant
• The second answer is often the real one
• Asking with care helps people access their own wisdom
• Insight doesn’t need to be immediate — just possible

See you next week. One more thought 👇

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That's it for this week. Thanks for reading, really hope this helped. Contact me if you think I can help you further at [email protected].

Happy thinking.