Great questions

Confronting questions:

Which of my current views would change if my incentives were different?
Which of my current views would I disagree with if I were born in a different country or generation?
What do I think is true but is actually just good marketing?
What do I ignore because it’s too painful to accept?
Who has the right answers but I ignore

love asking people: - what their “endgame” is - what they’re borderline overconfident about - what they’d want to do if they knew they’d be successful at it - what their fighting style is - what outfit they’d wear everyday if no one would notice they... See more

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Dream big questions:

‘What would I be like/spend my time doing if all my current major problems had been solved?’
‘What are the things I say I value but don’t act as if I value, and what would my life feel like on inside if I actually acted as if I valued those things?’
‘What am I afraid of doing, and what would my life be like if I wasn’t afraid of

Questions to ask your friends

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“Extreme” questions for brainstorming

If all our customers vanished, and we had to earn our growth and brand from scratch, what would we do?
If our biggest competitor copied every single feature we have, how would we still win?
If you were forced to increase your prices by 10x, what would you have to do to justify it?

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Duhigg, Supercommunicators

Can we re-frame this in terms of the customer’s problem?
What’s the soonest we could get this done?
What would you need to get this done tomorrow instead of next week?
What would we need to do to get twice as many customers? Ten times as many customers?
How does this relate to our goal? Is this the most important thing we can do for our goal?
What’s