Question Bank
A collection of interesting prompts for journaling, deep thinking, interviewing, and sparking meaningful conversations. The questions are filterable by categories.
Wisdom Cards
Use the arrows or keyboard ← → to explore. Each card pairs a question with a mental model.
Product DevelopmentIntensity 2/5
“What would this look like if it were easy?”
We often over-engineer solutions. This forces the simplest, most direct path to the surface.
Mental Model: Occam’s Razor
scalestrategy
Personal ReflectionIntensity 5/5
“How am I complicit in creating the conditions I say I don't want?”
Destroys the victim narrative and identifies exactly where you have the power to change.
Mental Model: Radical Responsibility
growthleadership
Personal ReflectionIntensity 4/5
“How could I create momentum by achieving my 10-year goals in the next six months?”
It reveals the 10x leverage points you are currently ignoring by removing the luxury of time.
Mental Model: Constraint Analysis
ambitiongrowth
Personal ReflectionIntensity 4/5
“What behavior you want to avoid that will fail you in life?”
Having a certain kind of temperament is more important than brains.
Mental Model: Inversion
growthleadership
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Question Bank Directory
120 questionsReady for a thought experiment?
| # | Question | Tags |
|---|---|---|
| 001 | How can I best support my own vulnerability? | growth |
| 002 | Why did you quit? | growth |
| 003 | Whose love do you crave, and what wound has that craving left on you? | growth |
| 004 | Are you copying someone else's life or designing your own? | growth |
| 005 | How do I become a more perfect instrument? | growth |
| 006 | Where am I currently feeling the most resistance? | growth |
| 007 | What would I do if I wanted to make today absolutely horrible? | growth |
| 008 | What would it take to be slightly kinder today? | growth |
| 009 | What would it take to complain less? | growth |
| 010 | Where am I making things more complex than they need to be? | growth |
| 011 | What would this look like if it were easy? | growth |
| 012 | What if I did the exact opposite in every area of my life for a week? | growth |
| 013 | If I could only work for four hours this week, what would I work on? | growth |
| 014 | How could I achieve my 10-year goals in the next six months? | growth |
| 015 | How would the type of person I want to become handle this situation? | growth |
| 016 | What would I do if it was impossible for me to fail? | growth |
| 017 | How am I complicit in creating the conditions I say I don't want? | growth |
| 018 | Is there something you should measure in your life that you currently don’t? | growth |
| 019 | What is the most impressive thing that you have built or achieved? | growth |
| 020 | Is there anyone in your network you wish you could apprentice under for a few weeks? | growth |
| 021 | What are the habits you wish you had? | growth |
| 022 | Is this current effort 'activity' or 'progress'? | growth |
| 023 | Where is the body sensation arising independent of the thought? | growth |
| 024 | Who really enriched your life this year in a big way? | growth |
| 025 | How will you protect the climate within your skull? | growth |
| 026 | What is the easiest thing you could do to improve your life, and why aren't you doing it? | growth |
| 027 | What have you changed your mind about recently? | growth |
| 028 | What if I could only subtract to solve problems? | growth |
| 029 | How often are you lonely, and how are you dealing with it? | growth |
| 030 | What are you spending most of your time and energy on? Is it worth it? | growth |
| 031 | What problems in your life do you feel you could solve if you were smarter or had more resources? | growth |
| 032 | Who is the most important person in your life that you are willing to live and die for? | growth |
| 033 | What in your life feels excessive? How would it feel to reduce it? | growth |
| 034 | In what ways are you a bad influence on those around you? | growth |
| 035 | What efforts should you realistically be abandoning? | growth |
| 036 | What have you abandoned that you could probably succeed at if you tried harder? | growth |
| 037 | If you could only give one single answer to anyone you meet, what would it be? | conversational |
| 038 | What’s one thing you’ve figured out in life that most others probably haven’t? | conversational |
| 039 | What is your strategy for a hotel breakfast buffet? | conversational |
| 040 | What is one question you find yourself asking over and over again? | conversational |
| 041 | How does the lighting touch the ground (what is the first step toward the vision)? | conversational |
| 042 | What piece of advice would you give to your older self? | conversational |
| 043 | Imagine you are on your deathbed; what do you wish you did more of? | conversational |
| 044 | Have you seen someone recently do great work that’s gone unnoticed? | conversational |
| 045 | What does your ideal day look like? | conversational |
| 046 | Given the choice of anyone in the world, whom would you want as a dinner guest? | conversational |
| 047 | Before making a call, do you ever rehearse what you are going to say? | conversational |
| 048 | If you could wake up tomorrow having gained one quality or ability, what would it be? | conversational |
| 049 | Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it? | conversational |
| 050 | What do you value most in a friendship? | conversational |
| 051 | What is your most treasured memory? | conversational |
| 052 | If you knew that in one year you would die suddenly, would you change anything about the way you are living? | conversational |
| 053 | Your house catches fire. After saving loved ones and pets, you can save one item. What is it? | conversational |
| 054 | Why are kids not taught to edit? | conversational |
| 055 | Where does courage come from, and how do we get more of it? | conversational |
| 056 | What are some tips for the ability to hold two opposing views at the same time? | conversational |
| 057 | What experiences remind you how malleable the world really is? | conversational |
| 058 | What is human dignity made of? | conversational |
| 059 | What is the inverse of loneliness? | conversational |
| 060 | What game are you playing? | conversational |
| 061 | How do you develop trust with others in harsh environments? | conversational |
| 062 | Why do American houses look the same? | conversational |
| 063 | Why do kids learn about dinosaurs before learning about clear thinking? | conversational |
| 064 | What is the highest and best use of you? | conversational |
| 065 | What are you abundant in? What do you lack? | conversational |
| 066 | What does this narrative do to my being? | conversational |
| 067 | What comes first: safety or disclosure? | conversational |
| 068 | What is a sign of intelligence that most confuse with stupidity? | conversational |
| 069 | What is standing between me and being present right now? | conversational |
| 070 | Which emotions are you not allowed to feel? | conversational |
| 071 | What would you do if you were much braver than you are? | conversational |
| 072 | What two films would you like to combine into one? | conversational |
| 073 | What's an honest slogan for a famous brand? | conversational |
| 074 | Where is the line between soup and cereal? | conversational |
| 075 | What's better broken than whole? | conversational |
| 076 | Which apocalyptic dystopia do you think is most likely? | conversational |
| 077 | Should kidneys be able to be bought and sold? | conversational |
| 078 | What are the major values or principles that you live by? | life |
| 079 | When does pain facilitate greatness? | life |
| 080 | Where would we be without the intellectual generosity of our ancestors? | life |
| 081 | What important truth do very few people agree with you on? | life |
| 082 | Is scientific truth dangerous? | life |
| 083 | If language influences how we perceive color, what else is it changing our perception of? | life |
| 084 | Does the idea of total freedom make sense? | life |
| 085 | Is it possible to prove that other people have consciousness? | life |
| 086 | Do questions deserve answers? | life |
| 087 | What is the diseased tissue upon which the virus of ignorance gains purchase? | life |
| 088 | How does time work? | life |
| 089 | Who is in a position to set limits on what we will know? | life |
| 090 | At what scale do we want the product to operate? | product |
| 091 | What do dashboards actually do for us? | product |
| 092 | Why do the reluctant users hold back? | product |
| 093 | Why isn't someone already doing this? | product |
| 094 | What emotion do I want the other person to leave this meeting with? | product |
| 095 | Where or how do you spend a majority of your time, and what is your return on invested time? | product |
| 096 | What is really hard for new hires to get used to in this firm? | product |
| 097 | If you were a private business, how would you operate differently? | product |
| 098 | What three things would you do to destroy this business as quickly as possible? | product |
| 099 | If you were away for one year, which key metrics would best tell you how the business was doing? | product |
| 100 | What is your comparative advantage? | product |
| 101 | In which single area of life do you have the best taste? | product |
| 102 | Which functions in the business could you outsource if you really had to? | product |
| 103 | When do you choose to build versus buy? | product |
| 104 | What happens when a company stops believing in secrets? | product |
| 105 | What is the motivation in business when P&L is the ultimate scoreboard? | product |
| 106 | Why not invest in a cheap, globally diversified basket of ETFs and do something else instead? | investing |
| 107 | How do you deal with ideological contradictions in an investment? | investing |
| 108 | When and why did you start believing it was skill and not luck? | investing |
| 109 | What is your process to reduce errors of omission? | investing |
| 110 | How would you know when there was no more edge at your table? | investing |
| 111 | What was the scariest, darkest moment of your career, and how did you get through it? | investing |
| 112 | How often do you guess? | investing |
| 113 | How much is enough? | investing |
| 114 | How do you size positions? | investing |
| 115 | What are your blind spots? | investing |
| 116 | What is your circle of competence, and how long did it take to define it? | investing |
| 117 | How do you mitigate bias in your decision process? | investing |
| 118 | Is there any difference between speculation and gambling? Does speculation presuppose intellectual effort? | investing |
| 119 | How can people avoid being swept up in a popular delusion? | investing |
| 120 | What company do you despise? | investing |