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:
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.
"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 Ask this when: • They're thinking too small • You want to generate bigger and bolder ideas Breakthrough outdated paradigms.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)
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
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)
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.
