Ask Better Questions
Questions are powerful when you are curious. Questions are to discover. Not to influence.
The older I get, the more time I spend—as a percentage of each day—on crafting better questions. In my experience, going from 1x to 10x, from 10x to 100x, and from 100x to (when Lady Luck really smiles) 1000x returns in various areas has been a product of better questions. – Tim Ferriss. Tribe of Mentors
Drive more questions. It’s under-used. Create a culture of curiosity. Questioning defines and structures what we don’t know.
Improve time management
- Where (life or work) are you pursuing comfort over the right discomfort?
- Are you judging yourself by standards that can never be met? Factor in second order effects
- In what ways have you yet to accept who you are, and bit the person you believe you ought to be?
- Where are you holding back until you feel like you know something? Everyone is winging it
- How would you spend your days differently if you didn’t care so much about seeing your actions reach fruition? Process vs outcome
Ask Founders
- What are some small things your organization does really well, and you’re proud of? I’d love to learn what you do and how it came about
- What are the top 3 principles your company lives by? If you had to drop one, which two would you keep?
Learn from people
- ⭐ What do you know better than most people? (Mine may be Calvin & Hobbes)
- What are the top 5 non-intuitive principles in that field?
- Quiz me about your field.
- What Book, Movie, Gadget would you recommend?
- What Technology caught your attention recently?
- What 3 things have you learnt in the last 30 days?
Discover people
- ⭐ What do you like most about what you’re doing? How did you get into this?
- What do you do in your spare time, on weekends?
- What’s most important to you right now?
- What got you into this line of business?
- Where do you decide based on emotion more than reason?
- What’s something you probably know better than anyone else? Mine may be Calvin & Hobbes
- What’s an unusual habit you have that you love?
- If you could go back 20 years, what advice would you give yourself?
- If you could live anywhere, where would it be?
- What would your autobiography be titled?
- What got you curious recently?
Discover contrarianism / independent thinking
- Do you ever find there are things about you that people misunderstand?
- What important truth do very few people agree with you on?
- What’s an accepted idea that you believe will turn out to be wrong?
Introspection
- How would you/we REALLY answer “How are you”?
- What prompted you to call us/take this meeting?
Repeated conversation
- How was your weekend? What plans for this weekend?
- What’s the best/worst/biggest/toughest/proudest/happiest thing you did since the last spoke?
- How did that thing you were talking about last time turn out?
- How are your children/spouse/relatives you recently mentioned?
Priorities
- Remember: if they don’t share, its because YOU haven’t been the person they can share with. That’s not wrong. It’s just there. Can I be in your circle of trust? I care.
- What are your personal goals and priorities right now?
- If you could have one ‘do over’ in your life, what would you do differently?
- On 31 Dec, when you look back at the year, what’s one think you’d feel really good accomplishing?
- (What do you want?) What’s the future you’re committed to? For your family? For your career?
- What areas of life are working well and not so well?
- What’s your biggest priority or focus right now? Why?
- What are you most proud of?
- Who among your friends would you invest time in? Who would you short? Why? What should you therefore strive to be?
Questions to evaluate
- What’s your go-to comfort food?
- This can reveal cultural background or personal preferences.
- Do you have any pets?
- This can indicate whether they are an animal lover and what kind of commitment they are willing to make for caregiving.
- What’s your favorite season and why?
- This can reveal their preferred activities and whether they like change or consistency.
- What’s the last thing you learned that fascinated you?
- This can show you what they find intellectually stimulating.
- What’s your favorite type of music?
- This can give you a glimpse into their emotional landscape and cultural leanings.
- Are you a morning person or a night owl?
- This can indicate their productivity patterns and lifestyle.
- What’s your dream job?
- This can reveal their ambitions and what they find fulfilling in work.
- What’s your favorite way to relax and unwind?
- This can tell you about their stress management techniques and what they find calming.
- Do you like to travel? If so, where’s your favorite destination?
- This can indicate their openness to new experiences and cultural diversity.
- What’s a skill you’d like to learn?
- This can reveal their aspirations and areas where they want to grow.
- How do you handle stress or conflict?
- This can give you an idea of their emotional intelligence and coping mechanisms.
- What’s your favorite childhood memory?
- This can offer a glimpse into their upbringing and what they find nostalgic.
- What’s something you’re grateful for?
- This can indicate their general outlook on life and what they value.
Discover from signals
- Not mentioning / avoiding => Significance
- … a person by name
- … a target to achieve
- Lack of attention to detail => Giving up
- Defiance => Giving up, it’s impossible
Discover personality
- What skills do you value in your team? (These are what they value in themselves.)
Find what’s missing
- How do you feel about this project right now?
- Specific: Energized, Drained, Frustrated, Overwhelmed, …
- Do you feel equipped for what you’re planning?
- What’s standing in your way?
- What have you identified as the main bottlenecks?
- What is your biggest worry right now about this project, and why?
- What is one challenge you wish you could disappear with a magic wand?
- What can you control?
- What is out of your control (and therefore not where you should focus your energy)?
… or the cause
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When did you first start doing this? In childhood…
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AVOID: What’s your probem?. Confrontational. Leads to “I don’t have a problem…”
Understand the importance / impact
- How important is aspect of your life to you?
- When do you want to make this happen?
- What will happen if you don’t take this step? What’s the impact of not achieving this?
- Why not continue with your current approach?
- What will things look like after you’ve been successful?
- How could things be much worse right now?
- Are you willing to invest X for this future? You can say yes, or no
Expand their thinking / possibilities
- What have you tried so far in solving the problem?
- How would it be if that were there/not there in your life?
- What has worked well and what has not worked well? What has made it so?
- Distancing: What would you advice a friend who had this same problem?
- Distancing: What would (an expert, well-wisher) do in your place?
- Inversion: What can you do to AVOID solving this problem?
- What’s more important to you? Your complaints or your commitments?
- What would this look like if it were easy? (Tim Ferris, Tribe of Mentors)
- What if? What possibilities open up (in a crazy alternate universe) if …?
- What is one wild idea you have about solving the problem that you’d like to try?
- What do you need most right now?
- Who do you need to BE to get this done?
- How do you justify where you are right now? What makes it OK? (Others are at fault. Circumstances. It’s OK. Things take time. I can’t control it. etc)
- Which of these is a physical impossibility? Which is influenceable?
- Who (famous real or fictional person) do you wish were here to solve your problem? How would they (e.g. Feynman) have solved it?
- A startup is a discovery process to answer a shared question. Frame the mission as a “How might we” question & encourage people to participate. That takes courage and confidence.
Find parallels
- ⭐ When else have you experienced similar situations? What was the outcome of that?
- Who else do you know has been in a similar situation? What happened?
Explore their learning / understanding
- What did you understand from this?
- Implication: What does this mean for you? What do you take away?
- Emotion: How do you feel about it?
- Reason: Why do you think I shared this?
Get permission
- May I make a request?
- May I partner with you to fulfilling this goal?
- What can I do to help? (Not: IS there anything I can do to help. OFFER help)
- Who else could you ask for help/bring into the project?
Change their mind
- (Give them time. Emotional reactions fade away)
- (Acknowledge your inauthenticity)
- (Listen better. Understand WHY they have a point of view, and VANISH it?)
- GET PERMISSION. Then ask: What’s the risk if you (do something bad that you want to)?
- When someone hates a group
- Name someone specifically and ask “Do you hate him? Why? Do you know him?”
- “What all do you have in common with them?”
- Best question: “Birth is arbitrary. How would you think if you were born among them?”
Probe or dig deeper
More details
- How is that for you?
- Go on…
- What happened?
- For example?
- How do you mean?
- WHY is that?
- How do you FEEL about that?
Fork
- ⭐ Why is this important to you?
- How did that impact you?
- Who else was impacted?
- What other thoughts do you have about that?
Counter question
- (Person gives complement.) I’m curious. What did you like, specifically? Why that aspect?
- (Person asks a question.) What’s interesting about that question is … - why do you ask that?
- (Person asks a question.) I’m thinking… but what is YOUR perspective on that?
- (Person asks a question.) What have others said about that?
Hold to account
- What did you have in mind when you committed to this last week?
- You generally finish what you promise. How did this slip?
- What’s the impact? On you? On me? On the team? On the project? On the future?
- Knowing this, what system could you set up to prevent recurrence?
Goal setting
- If no spare capacity: go for SMALL WINS
- Else if failing: set SMALL EXPERIMENTS (learn from small failures)
- Else if successful: set STRETCH GOALS
Principles
- Listen. With care
- Appreciate. Genuinely
- Engage. Talk about their interests
- Delight. Laugh with delight. Radiate inner excitement
Tactics
- Prefer follow-up questions. They signal care/interest.
- To get more information:
- Use a casual tone. No significance.
- Let people know they can change their answers.
- Frame tough questions using pessimistic assumptions. “We’re likely to miss targets, right?”
- Start with toughest question in competitive conversation, easies in cooperative.
- To pin down evasive answers, ask yes/no questions. Probe deeper.
Reflexive questions for blindspots
- What questions can I ask people so that I can get them to coach me?
- What would X say if I asked them this?
Get feedback on what we said
- What do you think?
- What did you hear from me?
- How do you feel about this?
- Does this make sense?
- Anything to add?
Motivation
- In 6 months, what would you need have done to feel proud of it?
- How can we make this more interesting for ourselves?
Teach listening
- ⭐ When was the last you learned something new about your father — that blew your mind?