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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:
• They're thinking too small
• 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Breakthrough outdated paradigms.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:
• They're learning something new
• The subject is complex
• 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:
• 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:
• They have a new product idea

Follow-up actions:
• Work backward from the customer POV
• 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:
• There's a bias towards instant gratification
• 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:
• 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:
• You hear the words "have to" or "must"
• 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:
• Specifying their goals/ideal outcome
"What would that give you that you wouldn't otherwise have?"

Ask this when:
• Clarifying desires
• 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:
• They're lacking confidence
• 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:
• 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:
• Clarifying their purpose
• 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.


P.S. If you like personal development, you'll love my weekly newsletter (it’s free).

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