
No, me neither – but it’s a useful challenge, because when someone brings you a problem, the most valuable thing you can do isn’t always to help them find the answer.
Sometimes it’s to help them find a better question.
Here are 10 questions I use to open up their thinking:
- Find the question behind the question
If this isn’t the real problem, what might be?
- Force a trade-off
By saying yes to this, what are you saying no to?
- Change the scale
If this problem were 10x bigger, what would suddenly matter most?
- Go down the rabbit hole
If we pursued that thought for 10 minutes, where might it take us?
- Surface hidden risks
Imagine it’s six months from now & this has failed. What went wrong?
- Borrow someone else’s brain
How would a designer, engineer, psychologist or superhero approach this?
- Hunt for anomalies
Who is succeeding despite doing the opposite?
- Remove the obvious options
What would you do if neither of these choices were available?
- Make room for the unexpected
What would surprise you if it turned out to be important?
- Question the need to act
What happens if you do nothing?
Good problem-solving isn’t just about getting to answers faster, sometimes it’s about asking a question that takes the conversation where nobody expected it to go.
If you’re trying to better understand a problem & want some help with some different thinking, message me here or at rupert@strongerhumans.com.





