Question Bank
A collection of interesting prompts for journaling, deep thinking, interviewing, and sparking meaningful conversations. The questions are filterable by categories.
High Signal Questions
Below are some high signal questions that help you gain widom and insights. 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 |