17 Tweets 23 reads Apr 04, 2023
Asking good questions is a superpower.
They expand minds, generate insights, and make you look smart.
12 of the best questions to do just that:
"How can you achieve your 10-year plan in the next 6 months?"
Ask this when:
β€’ They're thinking too small
β€’ You want to generate bigger and bolder ideas
Breakthrough outdated paradigms.
(Source: Peter Thiel)
The Feynman Technique
"How would you teach it to a child?"
Ask this when:
β€’ They're learning something new
β€’ The subject is complex
β€’ They're formulating "how-to" instructions
Encourage them to return to learning, fill in knowledge gaps, and simplify further.
The 5 Whys Method
"Why?" (Repeat 3-5 times)
Ask this when:
β€’ You want to uncover root causes, not proximate
Proximate = what immediately caused something to happen.
Root = the real reason something happened
Be hard on the problem, soft on the person.
(H/T: Sakichi Toyoda)
Amazon's Working Backward Method
"What would a press release for this product say?"
Ask this when:
β€’ They have a new product idea
Follow-up actions:
β€’ Work backward from the customer POV
β€’ Draft an FAQ + press release BEFORE building the product
Second Order Thinking
"And then what?"
"What do the consequences look like in 10 minutes? 10 months? 10 Years?"
Ask this when:
β€’ There's a bias towards instant gratification
β€’ Thinking through time
(Source: Farnam Street)
Second Order Thinking Cont'd
Many extraordinary things in life are first-order negative, second-order positive.
Ex: Starting a new workout regimen.
It's painful at first, with little instant gratification (negative).
But there IS a long-term health payoff (positive).
"How have you been complicit in creating the conditions you say you don't want?"
Ask this when:
β€’ They don't own their outcomes
First, build rapport and show positive intention.
They'll identify negative behaviors and regain their locus of control.
(Source: Jerry Colonna)
"What would happen if you didn't have to?"
Ask this when:
β€’ You hear the words "have to" or "must"
β€’ You notice unhealthy stress/anxiety
Ex: "I have to get into Harvard."
Expand their attractive options set = reduce stress.
"If there was a miracle tonight, and when you woke up tomorrow…
everything [in this area of your life/work] was exactly as you'd like it to be,
how would you know a miracle occurred?"
"What would you see, hear and feel?"
Ask this when:
β€’ Specifying their goals/ideal outcome
"What would that give you that you wouldn't otherwise have?"
Ask this when:
β€’ Clarifying desires
β€’ Shifting focus to gratitude
As @Naval says, "Play stupid games, win stupid prizes."
This question often reveals whether the prize is worth it.
"What are you like when you're at your best?"
Ask this when:
β€’ They're lacking confidence
β€’ They're seeking life direction
Listen for skills and qualities that might align with a fulfilling career.
"What would you do if you knew it was OK to fail?"
Ask this when:
β€’ Fear and perfectionism are holding them back
In the words of Adam Grant:
"The greatest originals are the ones who fail the most, because they're the ones who try the most."
The Joe Rogan Razor
"What would you do right now if a documentary crew were following you around?"
Ask this when:
β€’ Clarifying their purpose
β€’ There's an ethical decision
Rogan says the best life advice he's ever received:
Live your life like you're the hero in the movie.
One final thing:
Be your own best coach.
Ask these questions to yourself, too.
You'll be dangerous.
Thanks for reading! Follow me @SystemSunday for more content like this.

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