The Mihir Chronicles

On Questions

March 26, 2022

I have always admired people who can ask great questions. Those who ask great questions possess the key to genuine curiosity. Question is a powerful tool to learn anything. If I ask enough questions, I am certainly positive that I can trace back to the first question ever asked, but that is an exercise for never.

What is a question?

My interest lies on how to master the art of asking quality questions to learn anything in life. But what is a question? Wikipedia describes it as:

A question is an utterance which typically functions as a request for information, which is expected to be provided in the form of an answer.

Wikipedia goes on further that at linguistically level, a question can be defined on three levels:

  1. At the level of semantics, a question is defined by its ability to establish a set of logically possible answers.
  2. At the level of pragmatics, a question is an illocutionary category of speech act which seeks to obtain information from the addressee.
  3. At the level of syntax, the interrogative is a type of clause which is characteristically associated with questions, and defined by certain grammatical rules.

On the last point, questions are often conflated with interrogatives, which are the grammatical forms typically used to achieve them. Rhetorical questions, for example, are interrogative in form but may not be considered true questions as they are not expected to be answered.

The purpose of this deep dive is to explore open-ended questions for better conversations and drive personal growth for curious people.

What is a quality question?

What is the purpose of asking high quality questions? A quality question “reframes” the knowledge allowing to build further conviction or “refactors” an existing belief. It allows you to think about the current information and finding the gaps which triggers further questions. Most questions would never change your existing mental models or body of knowledge, but great quality questions will allow you to question your current beliefs which then allows you to adapt your beliefs over time.

If you are reading a murder novel, asking “who was the murderer?” is a less fruitful question than “why did the dogs in the house didn't bark?” The second question is a good indicator of a curious mind. The first question alone is less directional towards the answer. A good question cuts to the heart of anomaly, the answer to which would crack the larger problem open.

Socratic method

The trial of Socrates was a controversial case because the citizen of Athens knew him as an intellectual and moral citizen of their society. However, Socrates was sentenced to death due to the consequence of asking politico-philosophic questions of his students. Plato captured the presentation of the trial and death of Socrates that inspired many people. Plato called him “the wisest and most just of all men” who demonstrated the defects of democracy.

The Socratic approach to questioning has stood the test of time. The Socratic method is an effective way to explore ideas in depth. It is based on the practice of disciplined, thoughtful dialogue. In this technique, the teacher professes ignorance of the topic in order to engage in dialogue with the students. With this “acting dumb,” the student develops the fullest possible knowledge about the topic.

Teachers promote independent thinking in their students and give them ownership of what they are learning. Higher-level thinking skills are present while students think, discuss, debate, evaluate, and analyze content through their own thinking and the thinking of those around them. Socratic method is used in many disciplines and institutions including the US Supreme Court.

In Plato's early dialogues, the elenchus is the technique Socrates uses to investigate, for example, the nature or definition of ethical concepts such as justice or virtue.

  1. Socrates' interlocutor asserts a thesis, for example, “Courage is endurance of the soul.”
  2. Socrates decides whether the thesis is false and targets for refutation.
  3. Socrates secures his interlocutor’s agreement to further premises, for example “Courage is a fine thing” and “Ignorant endurance is not a fine thing.”
  4. Socrates then argues, and the interlocutor agrees, these further premises imply the contrary of the original thesis; in this case, it leads to, “Courage is not endurance of the soul.”
  5. Socrates then claims he has shown his interlocutor's thesis is false, and its negation is true.

The essential component of the Socratic method uses questions to examine the values, principles, and beliefs of people. The Socratic method focuses on moral education, on how one ought to live. The Socratic method demands a classroom environment characterized by productive discomfort. The Socratic method is better used to demonstrate complexity, difficulty, and uncertainty than at eliciting facts about the world.

Paul Graham on questions

  • Few grasp this. One of the biggest misconceptions about new ideas is about the ratio of question to answer in their composition. People think big ideas are answers, but often the real insight was in the question.
  • Part of the reason we underrate questions is the way they're used in schools. In schools they tend to exist only briefly before being answered, like unstable particles. But a really good question can be much more than that. A really good question is a partial discovery. How do new species arise?
  • Unanswered questions can be uncomfortable things to carry around with you. But the more you're carrying, the greater the chance of noticing a solution — or perhaps even more excitingly, noticing that two unanswered questions are the same.
  • Sometimes you carry a question for a long time. Great work often comes from returning to a question you first noticed years before — in your childhood, even — and couldn't stop thinking about. People talk a lot about the importance of keeping your youthful dreams alive, but it's just as important to keep your youthful questions alive.
  • This is one of the places where actual expertise differs most from the popular picture of it. In the popular picture, experts are certain. But actually the more puzzled you are, the better, so long as (a) the things you're puzzled about matter, and (b) no one else understands them either.
  • You have to be comfortable enough with the world being full of puzzles that you're willing to see them, but not so comfortable that you don't want to solve them.
  • It's a great thing to be rich in unanswered questions. And this is one of those situations where the rich get richer, because the best way to acquire new questions is to try answering existing ones. Questions don't just lead to answers, but also to more questions.
  • The best questions grow in the answering. You notice a thread protruding from the current paradigm and try pulling on it, and it just gets longer and longer. So don't require a question to be obviously big before you try answering it. You can rarely predict that. It's hard enough even to notice the thread, let alone to predict how much will unravel if you pull on it.
  • It's better to be promiscuously curious — to pull a little bit on a lot of threads, and see what happens. Big things start small. The initial versions of big things were often just experiments, or side projects, or talks, which then grew into something bigger. So start lots of small things.
  • Being prolific is underrated. The more different things you try, the greater the chance of discovering something new. Understand, though, that trying lots of things will mean trying lots of things that don't work. You can't have a lot of good ideas without also having a lot of bad ones.

Warren Berger on questions

I am a member of LTCWRK which is a community of curious people. Recently, a lecture was held by Warner Berger who is an author of several books on this particular topic. Some of my notes below from the lecture:

  • There are negative/dark side of questions:
    • Questions can be confrontational.
    • Questioning authority can have consequences.
    • Questions get used for a lot of purposes. Not all of them are good.
      • Someone with an agenda especially political figure with an agenda.
      • They are not used for the purpose of learning but to drive an agenda which discourages an open debate.
  • Steve Jobs was the architect of questions. He used it as an everyday tool. He used the philosophy of Zen, the beginner’s mind which is to ask questions while emptying your mind. He used “why” every day to challenge himself and his employees to keep everyone on their toes.
  • Questions reveal vulnerability. We ask less questions as we age. People (leaders) want to preserve their identity, age and authority so they don’t ask enough questions. Humility comes into play while asking questions.
    • Humility & confidence are both important elements of questions.
    • You need confidence to ask questions, but you also need humility to be vulnerable to ask questions.
  • Kids don’t have egos, but adults do which prevents them to ask questions. This is why kids are better.
    • It’s this tool that allows us to learn. It’s the question. What a beautiful thing.
    • Kids are not afraid to use it. They are good at open-ended questions.
    • But we can do something better than kids. We can moderate our questions that are less annoying.
  • If you don’t ask questions, you are putting on an act.
  • All innovation comes from big open-ended questions. Ask yourself, “what are some of the radical things we can do?”
  • A good question has some element of curiosity. The way to determine if a question is authentic if it has the following elements:
    • Good faith
    • Purpose of curiosity & learning
    • Open mindedness
  • Frameworks to use:
    • Sandwich framework
      • Start with “I am curious” then ask the question followed by providing a rationale for that question For example, “I am curious, why do we do [x]? I am asking because of [y] rational.”
      • This is a great framework to ask questions. It gives the listener a warning, a 2-second warning, when you start with stating that you are curious and then providing a rational towards the end.
    • Self-taught questions are great to bring perspective in your personal life.
      • Shift your perspective when in situational events by asking, “what would [x] person do?” What would Abraham Lincoln do? What would a 90-year-old me do?
    • Constraint on-off questions
      • On: what would I do if I had 24 hours to live?
      • Off: what would I do if I had all the budget in the world to build a product?
        • AirBnB uses this a lot while defining user experience. “What would an 11/10 experience look like?” Of course, not feasible, but allows learning about all the possibilities by exploring open-ended questions.
  • Questions are great to break mental traps, biases and prejudices based on past-experiences. We are wired in this way since the beginning of our days. So a tool like this is super helpful to break the conditioning. Use self-taught questions to understand these self-constructed biases. This is called critical thinking.
    • Business leaders are overconfident in their gut decisions, but science disagrees. Spend time avoiding your gut reaction by asking open-ended questions.
    • Avoid recency bias when asking questions.
  • A good practice exercise is to journal about the most important question of the day.
  • Question requires solving for a puzzle which our brains are wired to do. Don’t try to get answers immediately. Think deep and broad to solve it.
  • Don’t lead with questions with pre-meditated answers or outcomes. They are not good for learning and exploring. However, they do have a place:
    • They have a role while teaching others especially in education space. Teachers do it a lot.
    • Socrates did that during his trial with pupils.
    • Even people with agenda do it. Be careful.

Types of questions

  • Leading question: A leading question cannot be answered by a simple “Yes” or “No.” It requires the person you're interacting with to utter more than one syllable. Often, once you get the momentum of an answer going, the person will continue talking. Another key is to be curious. A genuinely interesting question will get a boat loads of love because people love feeling respected for their opinion and knowledge.
  • Closed question: A closed question is a question that has only one answer. For example: “Do you file your taxes?” You will most likely get a response “Yes” or “No.” All closed questions lead to a tense atmosphere since it narrows the space for a partner to have a conversation with. It also has a purpose when you are trying to obtain an agreement, but less fruitful when you are trying to explore something. This is useful when you are trying to get an agreement from your significant other to go on a date. It'd be less useful if the other person goes on a tangent before answering a yes or a no.
  • Open question: An open question is a question that requires some explanation and implies a detailed answer. You can use the open questions to get additional information or find out the real motives of the interlocutor. Often, such questions begin with words: why, what or how. Open-ended questions bring the partner you are having a conversation with in an active state and eliminates the barriers.
  • Rhetorical questions: A rhetorical question is a question that does not require a direct answer and is aiming of focusing their attention or pointing out unsolved problems. For example: “Are we holding a common opinion on this issue?” or “When do people finally learn to understand each other?” Proceed with caution as it is easy to slip into the dark side of questions.
  • Alternative question: An alternative question is an open question with several pre-prepared answers. For example: “When do you think is better to hold the next meeting? Can we meet this week again or the next one?” To talk more to the interlocutor, you can use the alternative questions. However, it is recommended to soften the alternative questions that may offend feelings of the interlocutor. For example, instead of the question, “What are you afraid of that is preventing you to get work done?” use the following, “Are there some circumstances that will prevent you from doing work on time?”
  • Provocative questions: Provocative questions can catch the interlocutor on the contradiction between what he says now and what he has said earlier. To use such type of questions is not the best way to gain authority. At best, your partner (or opponent) will look for revenge. This type leads to the dark side of questioning.

Question bank

Here is my ridiculously long list of good questions accumulated over the years from the internet, blogs, podcasts and personal notes. I use them to get a conversation going or poke holes into my existing beliefs or learn something new.

Category Questions
Growth How can I best support my own vulnerability?
Growth Why did you quit?
Growth Whose love do you crave? What wound has it left on you?
Growth Are you copying someone else's life? Or designing your own?
Growth How do I become a more perfect instrument?
Growth Where am I feeling the resistance?
Growth What would I do to make today horrible?
Growth What would it take to be kinder today?
Growth What would it take to complain less?
Growth Where am I making things more complex than they need to be?
Growth What would this look like if it were easy and hard?
Growth What if I did the opposite in every area?
Growth If I could only work for four hours this week, what would I work on?
Growth How could I achieve my 10-year goals in six months?
Growth How would the type of person I want to become handle this?
Growth What would I do if it was impossible for me to fail?
Growth How am I complicit in creating the conditions I say I don't want?
Growth Is there something you should measure in your life that you currently don’t?
Growth What is the most impressive thing that you have built or achieved?
Growth Is there anyone in your network you wish you could apprentice under for a few weeks?
Growth Where do you see yourself in [x] months/year from now?
Growth What are habits you wish you had?
Growth Is this activity or progress?
Growth Where/what is the body sensation arising independent of the thought? (deconstruction)
Growth Who really enriched your life this year in a big way? Who is someone you want to get to know better in the year ahead?
Growth Where and with whom were you most resentful in [year]? How can you get straight about your own needs and articulate them so you can stop feeling that shit in the following year?
Growth How will you protect the climate within your skull?
Growth What’s something you need that you don’t have?
Growth What is the easiest thing you could do to improve your life, and why aren't you doing it?
Growth What have you changed your mind about recently?
Growth What if I could only subtract to solve problems?
Growth Are you a good person?
Growth How can you deal with boredom?
Growth How often are you lonely? How are you dealing with loneliness?
Growth What are you spending most of your time and energy on? Is it worth it?
Growth What problems in your life do you feel like you could solve if you were smarter or had more resources?
Growth Can your friends trust you?
Growth Who is the most important person in your life that you are willing to live for and die for?
Growth What is the most important thing in your life, and what would you do if you were free to focus on it?
Growth What in your life feels excessive? How would it feel to reduce it?
Growth What brings you joy in life? Do you do too much of it or too little?
Growth In what ways are you a bad influence on those around you?
Growth Congratulations, all your hard work has paid off! How does it feel? Do you get the recognition you deserved? Was it worth it?
Growth What efforts should you realistically be abandoning?
Growth What are you not putting enough work into?
Growth What have you abandoned that you could probably succeed at if you tried harder?
Conversational If you could only give one single answer to anyone you meet, what would it be?
Conversational What’s one thing you’ve figured out in life that most others probably haven’t?
Conversational What is the one activity or person that makes you happiest in the world?
Conversational If you’re on vacation at a hotel with a great free breakfast buffet from 7AM-9AM - what’s your strategy?
Conversational If you had to articulate a mantra for [year], what would it be?
Conversational What is one question that you found yourself asking over and over again? What version of an answer are you living your way into?
Conversational How does the lighting touch the ground? (What's the first step towards the vision?)
Conversational Who made you smile today?
Conversational A genie appears in front of you and offers you one wish, what would that wish be?
Conversational What piece of advice would you give to your older self?
Conversational Imagine you are on your deathbed, what do you wish you did more in your life?
Conversational How could you be more useful to those around you?
Conversational Is there any part of your life you wish you had more influence on?
Conversational Have you seen something recently and thought to yourself ‘I wish I had done that’?
Conversational If you could pick up a new skill in an instant what would it be?
Conversational What are three things you are currently worried about?
Conversational When do you feel most productive at work?
Conversational Have you seen someone recently do great work that’s gone unnoticed?
Conversational What's not working in your life right now?
Conversational What is something you can apply to your life from the book you are reading now?
Conversational What are you most looking forward to?
Conversational What does your ideal day look like?
Conversational Given the choice of anyone in the world, whom would you want as a dinner guest?
Conversational Would you like to be famous? In what way?
Conversational Before making a telephone call, do you ever rehearse what you are going to say? Why?
Conversational When did you last sing to yourself? To someone else?
Conversational If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
Conversational Do you have a secret hunch about how you will die?
Conversational Name three things you and your partner appear to have in common.
Conversational For what in your life do you feel most grateful?
Conversational If you could change anything about the way you were raised, what would it be?
Conversational Take four minutes and tell your partner your life story in as much detail as possible.
Conversational If you could wake up tomorrow having gained one quality or ability, what would it be?
Conversational If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
Conversational Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
Conversational What do you value most in a friendship?
Conversational What does friendship mean to you?
Conversational What is your most treasured memory?
Conversational What is your most terrible memory?
Conversational If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
Conversational What roles do love and affection play in your life?
Conversational How close and warm is your family? Do you feel your childhood was happier than most other people’s?
Conversational How do you feel about your relationship with your mother?
Conversational Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
Conversational Of all the people in your family, whose death would you find most disturbing? Why?
Conversational Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.
Conversational What do you think were the ingredients in that encapsulated period of time that led to that spontaneous actualization or realization of feeling as you did?
Conversational How in holy hell have I become the janitor of a mountain of bullshit?
Conversational Why are kids not taught to edit?
Conversational Why don't kids read?
Conversational Why do people hate writing, and why do people think they can't write well?
Conversational Would Darwin have discovered evolution more quickly if he’d lived in the Information Age, with the Internet as we know it?
Conversational Where does courage come from, and how do we get more of it?
Conversational What is an example of passionate intensity leading to regress?
Conversational Why ask great questions?
Conversational Where does the magic lies?
Conversational How adaptable are we?
Conversational What are some tips for an ability to hold two opposing views at the same time?
Conversational What are the basic elements of conviction?
Conversational Where does ambition come from?
Conversational Does the rate of change in progress varies with age progression?
Conversational How do we turn off [fear] of [feeling insecure]?
Conversational How do you become [child like]?
Conversational What experiences remind you how malleable the world really is?
Conversational How do we get a group of hyper-alpha people to open up?
Conversational What works give you dignity?
Conversational What is human dignity made of?
Conversational What bends you out of shape so much? In other words, what frustrates you?
Conversational Where does our culture of commitment phobia come from?
Conversational How can you make higher-level decisions?
Conversational What are some of the asymmetries in the social domain?
Conversational Are you a cleverer questioner?
Conversational Do you attribute success to luck or skill?
Conversational What's one thing you've removed from your life that's made it significantly better?
Conversational How can we connect the ‘man on the spot’ knowledge of the world’s best talent curators with the blind, fat pocketbooks of our government?
Conversational Rich people need it. Poor people have it. If you eat it, you die. And when you die, you take it with you. What is it?
Conversational What’s it like to cherish the simple life but shoulder a level of fame that must feel suffocating?
Conversational Why do so many smart people fail to discover anything new?
Conversational What is inverse of loneliness?
Conversational What game are you playing? The philosopher Kwame Appiah writes that “in life, the challenge is not so much to figure out how best to play the game; the challenge is to figure out what game you’re playing.”
Conversational What is confidence?
Conversational Why did it take so long to accept facts of [covid]?
Conversational How do you balance the two logical vs rhetoric style?
Conversational How do you develop trust with others? Especially in harsh environments where striving for success is minimal.
Conversational How do you manage ego when it doesn’t go your way?
Conversational Are you [value, growth, performance, process, outcome, love, spiritual] driven?
Conversational Do you ever see founders that don't have some sort of similar extreme adversity early in their lives?
Conversational If there was a button that if you pressed it would retroactively make your childhood easy, would you press it?
Conversational Why do American houses look the same?
Conversational Why is there such a huge misconception of economics when it is the most important topic for a society?
Conversational Why on Earth do kids learn about dinosaurs before learning about clear thinking?
Conversational The wonder we should concern ourselves with: What else has been hidden by summary? What are the unseen things today that could be growing?
Conversational The world is happening. What are you doing about it despite lack of control?
Conversational What does gut feeling mean to you?
Conversational Why aren't we kinder?
Conversational Why are people so cooperative?
Conversational Looking back, what do you regret?
Conversational What is the highest and best use of you?
Conversational Are you spiritually fit?
Conversational What are you abundant in? What do you lack? How can you give more of what you’re abundant in to others today?
Conversational What would make your life easier?
Conversational How do you stay resilient?
Conversational Why read a lot?
Conversational What’s a low barrier-of-entry, high reward hobby you recently started and still pursue with joy?
Conversational Why [Austin?] What makes this city alive?
Conversational What does this narrative do to my being?
Conversational Why should the high-influence person listen to the low-influence person if the former sees the latter as having little to offer?
Conversational If advice is so often useless, why do people continue offering it?
Conversational What comes first, safety or disclosure?
Conversational Why do some people have an action for bias while others seem to make a lot of noise and go nowhere?
Conversational Did you have any experience early in your building creative things or putting out creative things where you were derivative?
Conversational What is a sign of intelligence that most confuse with a sign of stupidity?
Conversational How does habits create strength?
Conversational How to construct your tribe?
Conversational When to compare and not compare?
Conversational How lucky are we to live in this beautiful place?
Conversational What is standing between me & being present right now?
Conversational What's the successor to the book? And how could books be improved?
Conversational What's the successor to the scientific paper and the scientific journal?
Conversational Which story (book, film, whatever) have you most cried at and what about your life does it remind you of?
Conversational Which emotions are you not allowed to feel, and where did you learn it was unsafe to feel them?
Conversational Look around your environment. Now look again, but this time notice the thing you tried not to see the first time because it was making you anxious and avoidant. What is that thing and why is it scary?
Conversational You can swap lives with anyone you know. Who do you pick and why?
Conversational Congrats, you get a superpower! You may now experience one particular emotion, as strongly as you want, whenever you want to. Which emotion do you pick, and when do you use this power?
Conversational What in your life could you give up to make the world a better place? Why don't you?
Conversational If you were behaving unethically, how would you know? Is there anyone who you would trust to tell you?
Conversational What have you not yet acknowledged must end? Are you prepared for its absence?
Conversational What would you do if you were much braver than you are?
Conversational Consider the standards you hold yourself to. What would the world look like it they were widely adopted? Would any of them make things worse? Would people be happier?
Conversational What two films would you like to combine into one?
Conversational When was the last time you were hopelessly lost?
Conversational What’s your best example of correlation not equaling causation?
Conversational What’s quickly becoming obsolete?
Conversational Think of a brand, now what would an honest slogan for that brand be?
Conversational If you had a giraffe that you needed to hide, where would you hide it?
Conversational Where’s the line between soup and cereal?
Conversational What weird potato chip flavor that doesn’t exist would you like to try?
Conversational How much do you plan vs prepare for the future?
Conversational What profession doesn’t get enough credit or respect?
Conversational What’s better broken than whole?
Conversational What piece of “art” would you create if you had to pretend to be an artist and submit something to a gallery?
Conversational What’s the cutest thing you can imagine? Something so cute it’s almost painful.
Conversational What’s the biggest overreaction you’ve ever seen?
Conversational What’s the most physically painful thing you’ve ever experienced?
Conversational What’s the most emotionally painful thing you’ve ever experienced?
Conversational What topic could you spend hours talking about?
Conversational What’s your best example of easy come, easy go?
Conversational What was ruined because it became popular?
Conversational If cartoon physics suddenly replaced real physics, what are some things you would want to try?
Conversational What from the present will withstand the test of time?
Conversational How ambitious are you?
Conversational Who is the most creative person you know?
Conversational What trend are you tired of?
Conversational What’s your secret talent?
Conversational Do you have any memory of a moment that made you laugh so hard?
Conversational Which apocalyptic dystopia do you think is most likely?
Conversational What odd smell do you really enjoy?
Conversational What brand are you most loyal to?
Conversational What’s the most ridiculous animal on the planet?
Conversational What’s your best story from a wedding?
Conversational What was your most recent lie?
Conversational What’s the hardest you’ve ever worked?
Conversational What problem are you currently grappling with?
Conversational What riddles do you know?
Conversational Should kidneys be able to be bought and sold?
Conversational What food is delicious but a pain to eat?
Conversational What weird food combinations do you really enjoy?
Conversational Do you think that aliens exist?
Conversational What are you currently worried about?
Conversational Who do you go out of your way to be nice to?
For elders If a young person asked you, “What have you learned in your ____ years in this world,” what would you tell him or her?
For elders Some people say that they have had difficult or stressful experiences, but they have learned important lessons from them. Is that true for you too? Can you give an example?
For elders As you look back over your life, do you see any “turning points”; that is, a key event or experience that changed the course of your life or set you on a different track?
For elders What would you say you know now about living a happy and successful life that you didn’t know when you were twenty?
For elders What can younger people do to avoid having regrets later in life?
For elders What would you say are the major values or principles that you live by?
Philosophy When does pain facilitate greatness?
Philosophy Why being more intelligent is bad?
Philosophy What does free mean?
Philosophy What is process?
Philosophy How to explore?
Philosophy Why focus?
Philosophy Where would we be without the intellectual generosity of our ancestors?
Philosophy What are the change events that are bigger than you that you're riding?
Philosophy Can morals be derived from reason?
Philosophy Are we machines?
Philosophy Would you rather fight a horse-sized scorpion or 1,000 scorpion-sized horses?
Philosophy Would you rather fight a horse sized duck or 100 duck sized horses?
Philosophy What is science?
Philosophy What important truth do very few people agree with you on? (inspired by Peter Thiel
Philosophy Do people in wealthier countries have a moral obligation to help those in poorer countries?
Philosophy Is some degree of censorship necessary?
Philosophy Can scientific truth be dangerous?
Philosophy Do humans need to be governed?
Philosophy Do we understand the present better than the past?
Philosophy If language influences how we perceive color, what other things could languages be changing our perception of?
Philosophy Is memory sufficient to be a historian?
Philosophy Does language only serve to communicate?
Philosophy Are all truths demonstrable?
Philosophy Does the idea of total freedom make sense?
Philosophy How much does language affect our thinking?
Philosophy Is hierarchy necessary for all successful human communities?
Philosophy Is it possible to prove that other people besides yourself have consciousness?
Philosophy Are people ethically obligated to improve themselves?
Philosophy Is defending your rights the same as defending your interests?
Philosophy Do questions deserve answers?
Philosophy What is true about the conspiracy myth?
Philosophy What is it that makes the vast majority of humanity comply with a system that drives Earth and humankind to ruin?
Philosophy What is the diseased tissue upon which the virus of ignorance gains purchase?
Philosophy Do people in wealthier countries have a moral obligation to help those in poorer countries?
Philosophy Are “forces” fundamental? Is “energy” fundamental? Are “fields” fundamental?
Philosophy How does time work?
Philosophy Why did life emerge?
Philosophy Why did humans create religions?
Philosophy What makes you feel safe?
Philosophy How did Zen come to beginning?
Philosophy What is to be awakened?
Philosophy Who is in a position to set limits on what we will know?
Philosophy Do intellectuals have wisdom? Or are wise people intellectual?
Philosophy Is man related to something infinite or not?
Philosophy If nobody is around to hear a tree when it falls did it fall? If a tree falls in the forest and nobody is around to hear it, it didn’t fall.
Product At what scale do we want the product to operate?
Product What do dashboards do?
Product Why documentation culture?
Product What are bigger jobs to be done items?
Product What jobs to be done need to be enabled?
Product Which [Google] product or service don't make sense to you? Why?
Product How would you improve [Google's Chrome browser]?
Product How are you understanding customer needs?
Product What competition do you fear most?
Product What obstacles will you face, and how will you overcome them?
Product Who would be your next hire?
Product What domain expertise do you have?
Product How much does customer acquisition cost?
Product Six months from now, what's going to be your biggest problem?
Product What is your distribution strategy?
Product What are the top things users want?
Product How are you meeting customers?
Product Where do new users come from?
Product What is the next step with the product evolution?
Product What's the conversion rate?
Product Will your team stick at this?
Product Who would you hire, or how would you add to your team?
Product Why do the reluctant users hold back?
Product How big an opportunity is there?
Product What is your burn rate?
Product What is your user growth rate?
Product Why isn't someone already doing this?
Product What makes new users try you?
Product What do you understand about your users?
Product How is your product different?
Product Are you open to changing your idea?
Product Who is going to be your first paying customer?
Product What emotion do I want the other person to leave with?
Product What change do I want the other person to make?
Product What can I do in the meeting to increase the other person's trust in me?
Interview How to build a fantastic network?
Interview Where or how do you spend a majority of your time, and what do you use as a barometer for your return on invested time?
Interview Of your competitors, who do you respect the most and why?
Interview Tell me why you’ve been successful, and how do you sustain it? How do you measure whether you are successful?
Interview What three things would you tell a friend about how to be successful in your company?
Interview What is really hard for new hires to get used to in this firm?
Interview What do you want to be known for?
Interview If you were a private business, how would you operate differently?
Interview What do you like about working here?
Interview Who are your current and past mentors, and what impact did they have on your life?
Interview What three things would you do to destroy the business as quickly as possible? Give yourself a one-year time frame.
Interview If we were meeting three years from today, what would need to have happened during that time for you to feel happy about your progress?
Interview What type of information do you need on a weekly basis?
Interview If you were away for one year, which key metrics would best tell you how the business was doing?
Interview Why can’t other people do what you are doing?
Interview What's your comparative advantage? How do you invest in it and improve it to magnify the opportunities where that advantage is indispensable?
Interview Of all the businesses you’ve looked at, what’s the best one, and why?
Interview What are you compulsive about?
Interview Why, what and how. Great companies, highly successful companies have real clarity in these 3 things. So the why questions are the fundamental ones. Why do we exist? Why should someone want to work here? Why should we come and go the extra mile and care? That's about purpose. The what questions are: what are my products and services? What are the target customer segments I'm trying to serve? What is our business model? That's strategy. The how questions are: how are we going to behave? How are we going to operate as an organization and as a team? How are we going to bring our purpose and our culture to life? That's about culture.
Interview If [Company X] disappeared, what would happen? Does [Company X] have a reason to exist?
Interview In which (single) area of life do you have the best taste? Optional follow-up: Do you work in that area? Why or why not?
Interview Do management's capabilities fit with what the task is going to be for that company? Don't get overly persuaded by one person. Typically, the people that have risen to the top are great at storytelling, extraordinarily persuasive, and believe what they're saying. When we invest we are trying to invest in what a company will be, not what it was or what it is. There are no future facts. Form your own outlook separate from what management tells you.
Interview What's been your biggest recent error of omission and did you make any changes, even at the margin, to your process as a result of that error? Either the stock you wish had sold, the stock you wish you had bought. Ask this instead of the error of commission because everyone should be able to talk about their mistakes.
Interview Which functions in the business could you outsource if you really had to? And the purpose of that is to understand where the value is really being generated in the business, versus the ancillary activities that support that. That question is trying to understand what capability drives their competitive advantage.
Interview How much time or money would be needed to copy your products or services?
Interview What are the three most important financial and non-financial KPIs (key performance indicators) on your dashboard? What does management think is critical to the business that drives value?
Interview When do you choose to build versus buy? How do they make that decision of going to buy an asset versus go green field? What are common mistakes you've seen others make in the industry? This would be to get a sense of not just how the industry works, but also what management sees as a fatal flaw that they try to avoid—and whether they have a good understanding of what can break the business side; the risk management side of it.
Interview What happens when a company stops believing in secrets?
Interview How much of what you know about business is shaped by mistaken reactions to past mistakes?
Interview What would the ideal company culture look like?
Interview How to prevent bottleneck?
Interview How can people grow an online audience?
Interview How close to that 10 can you get when you’re first getting to know someone and deciding whether they are a fit for your team?
Interview Why can't we find workers?
Interview What is the motivation in business when P&L is the ultimate scoreboard?
Interview How to build a business that lasts 100 years?
Interview How to think clearly?
Interview What's the cost of doing a poor job?
Investing If you were to outrageously brag about something that makes you exceptional without fear of looking arrogant, what would it be?
Investing What skill or mindset of yours do you find the most difficult to transfer to even the most talented members of your team?
Investing Why not invest in a cheap, tax-efficient, globally diversified basket of ETFs and go do something else (more productive) instead?
Investing Why do you keep doing it? What is the compulsion that keeps you going? What itch always needs scratching?
Investing May I please see what's inside your portfolio?
Investing How do you deal with ideological contradictions, especially if you know an investment will be extremely lucrative but also conflict with your personal ethics/beliefs?
Investing When and why did you start believing it was skill and not luck?
Investing Who do you consider to be the best investor of all time?
Investing Where are you on the spectrum of faking it to making it and why? And in which direction?
Investing What is your process to reduce errors of omission?
Investing How would you know when there was no more edge at your table?
Investing What is the best improvement they've ever made to their decision-making process?
Investing What mistake do you keep making?
Investing What would you prefer? 100 VC-sized Softbanks or 1 Softbank-sized VC?
Investing What was the scariest darkest moment of your career, and how did you get through it?
Investing Why didn't you just buy FANG?
Investing What do you know about the world of investing today, that you wish you knew decades ago when you were first starting out?
Investing What are some techniques you use to “sit tight”, i.e. to avoid over-trading?
Investing How do you deal with feelings of isolation/being different?
Investing Is YOLO the new FOMO?
Investing What’s your one pick for the next decade and why?
Investing How often do you guess?
Investing How much is enough?
Investing How do you size positions?
Investing Why did you invest or pass?
Investing What’s shifting in society that you are positioned to capture value from?
Investing What are the top 3 mistakes that you see other investors making that you avoid?
Investing Who are your sounding boards/trusted advisors, and how did you choose them?
Investing When do you sell? Do you have a sell checklist?
Investing How does one identify value and growth traps?
Investing What are your blind spots?
Investing Describe your research process. How do you generate ideas, diligence process, decision to invest/not invest? What's your process, from idea, to implementation, to risk management, to exit?
Investing What is that one change in your process or behavior that has helped you the most in improving your investment outcomes?
Investing What do you consider your most entrenched priors/biases?
Investing How long did it take you to define and develop your circle of competence?
Investing How do you mitigate bias in your investment process?
Investing How long did it take to find the strategy that worked for you, and how did you commit to it without second guessing yourself?
Investing Do you still enjoy playing this game? Why or why not?
Investing What’s your information consumption looks like? I want to know how you isolate noises vs signals.
Investing Do you trust your gut? If so, what is your source of conviction?
Investing Is there any difference between speculation and gambling? The terms are often used interchangeably, but speculation presupposes intellectual
Investing Is speculation right?
Investing How can people avoid being swept up in a popular delusion?
Investing Investing is hard enough. Why make it harder by investing in industries with headwinds?
Investing What are the technological headwinds & the cost headwinds?
Investing What company do you despise?

Further reading