Striving for rigorous thinking over lazy thinking should be everyone’s goal. Rigorous thinking enforces people to defend their thesis and advocate their ideas. The ideas are backed by data rooted in reality. Lazy thinking is a black box of logic where people don’t know why something works.
Adult life is more than just a multiple-choice test. Go beyond “what?” and ask “how?” and “why?” Finding answers to “What are the main causes of lack of critical thinking?” can be answered with a quick web search. But this type of knowledge is superficial. To build rigorous knowledge, we need to go beyond simple facts and web search. We can all improve critical thinking by asking a few extra questions each day.
To be a successful investor, scientist, writer or a founder, it is not enough to follow the same prediction. Therefore, critical & independent thinking becomes important. Rigorous thinking implies being critical of information presented to you. Rigorous thinking implies being able to think for yourself. If everyone is hiking the same trail, should you be following the same trail? That is the essence of Rigorous and independent thinking.
Logical perspective is called upon us everyday while making critical decisions. However, the noise around us makes it very difficult to separate fact from opinion. Politics, religion and stock market direction yield useless discussion because they do not go anywhere. Beliefs become part of people’s identity and they are hard to mold once they harden.
We are constantly bombarded with new information, day in and day out, via our smartphones, our browsers, advertisements, digital news, and more. Take a look around you and you’ll find yourself surrounded by a data overload, but a drought of original thought. You are marinating yourself in the conventional wisdom. We take opinions as facts and as a single source of truth. It even seems at times like we have forgotten how to question and reason.
Liberal arts and humanity is not given the same importance as math and science in higher education today. It should be a reminder for us all that we are molded by our way of thinking. In that case, you can bet the decay of society will start accelerating if there is a broader decay of rigorous and independents thinking.
Great thinkers
Ralph Waldo Emerson on solitude:
He who should inspire and lead his race must be defended from travelling with the souls of other men, from living, breathing, reading, and writing in the daily, time-worn yoke of their opinions.
Emerson is suggesting to lead and avoid heading towards the cliff led by a common herd. To avoid falling over the cliff, you need to make solitude as your dear friend. Solitude and leadership is contradictory but that is the essence of leadership. Being able to think for yourself and make hard decisions for common good is required out of great leaders. [2]
Charlie Munger’s tip on improving the ability to hold opposing views:
Well I do have a tip at times in my life I've put myself to a standard that I think has helped me. I think I'm not really equipped to comment on this subject until I can state the arguments against my conclusion better than the people on the other side. If you do that all the time, if you're looking for disconfirming evidence and putting yourself on a grill to make that, that's a good way to help her move ignorance. What happens is that every human being tends to believe way more than he should in what he's worked hard to find out or what he's announced publicly that he already believes. In other words while we shout our knowledge out we're really pounding it in without we're not enlarging it and I was always aware of that and so I've accepted these damned annual meetings I'm pretty quiet.
I never allow myself to have an opinion on anything that I don’t know the other side’s argument better than they do.
George Orwell on lies from his 1984 book:
And if all others accepted the lie which the Party imposed—if all records told the same tale—then the lie passed into history and became truth. ‘Who controls the past’ ran the Party slogan, ‘controls the future: who controls the present controls the past.'
Emerson, Munger and Orwell are pushing for independent thinking and challenging conventional wisdom. Unfortunately, in our society thinking from the fundamentals or the source material is rare. We instead form conclusions after taking in layers and layers of overlapping information and opinions, without basing our reasoning on those essential fundamentals. Also rare is a deep, multi-faceted education, which contains a breadth of learning.
Socratic method
To ask continual questions, Socrates, a Greek philosopher who sought to get to the bottom of his students’ views used continual questions until a contradiction was exposed. This challenges the initial assumption of his students. Asking continual questions is known as the Socratic Method.
The Socratic Method pushes for critical thinking and finding holes in assumptions. Questions to promote critical thinking:
- Why does X cause Y to happen?
- How will making a decision impact others?
- What is the hardest part of this problem you are working on?
- How can you overcome constraints you are dealt with?
- Can you back your thesis with a set of data points?
- How did you know this?
- Why did you fail and what did you learn from it?
- What important truth do very few people agree with you on?
- Where does conviction and ambition come from? How can you get more of it?
- Why ask great questions?
Timeful vs timeless advice
Be critical of timeful vs timeless advice.
If one is equipped to think critically, can a person challenge conventional wisdom? One can start with understanding the basic elements of conventional wisdom. Buying a home to build wealth, for example, was relevant for a specific era, but might not be for many today.
Outsourcing decisions to recent history might sound novel and convenient, but can be dangerous because you have failed to explore why it’s conventional in the first place. Compounding doesn’t have the same magnitude of wealth accumulation when buying a home. Why is that? The elements of yesterday do not comply with elements today. Interest rate environment was different in the 70s than today. That is just one possible explanation. But one should compile all these elements and then try to answer the same question.
Challenging these types of conventional wisdom allows you to differentiate between timeliness and timelessness of advice. On a final note, we need to teach that doubt is not to be feared but welcomed and discussed. It’s OK to say, “I don’t know” and question everything, because that is when the independent thinkers inherent in all of us can rise.
Writing essays for critical thinking
We are taught in schools to write essays with introductions and conclusions. But a real essay should be for pure observations. Since high schools imitate universities, the entire experience of education is rooted in writing essays around English literature and defending the thesis. Defending a thesis comes from law, but that is pointless when writing essays for thinking.
Traditional essays do not allow to explore questions, but rather explore answers to a specific question. A quick web search can point me to all possible answers. I can beautify my essay with a flavor of rhetoric and perfect grammar. Paul Graham has written an excellent piece on this topic.
It's no wonder if this seems to the student a pointless exercise, because we're now three steps removed from real work: the students are imitating English professors, who are imitating classical scholars, who are merely the inheritors of a tradition growing out of what was, 700 years ago, fascinating and urgently needed work.
The other big difference between a real essay and the things they make you write in school is that a real essay doesn't take a position and then defend it. That principle, like the idea that we ought to be writing about literature, turns out to be another intellectual hangover of long forgotten origins.
Defending a position may be a necessary evil in a legal dispute, but it's not the best way to get at the truth, as I think lawyers would be the first to admit. It's not just that you miss subtleties this way. The real problem is that you can't change the question.
An essay is supposed to be a search for truth. It would be suspicious if it didn't meander.
If there's one piece of advice I would give about writing essays, it would be: don't do as you're told. Don't believe what you're supposed to. Don't write the essay readers expect; one learns nothing from what one expects. And don't write the way they taught you to in school.
Paul Graham on independent mindedness
There's room for a little novelty in most kinds of work, but in practice there's a fairly sharp distinction between the kinds of work where it's essential to be independent-minded, and the kinds where it's not. I wish someone had told me about this distinction when I was a kid, because it's one of the most important things to think about when you're deciding what kind of work you want to do. Do you want to do the kind of work where you can only win by thinking differently from everyone else? I suspect most people's unconscious mind will answer that question before their conscious mind has a chance to.
Independent-mindedness seems to be more a matter of nature than nurture. If you're naturally independent-minded, you're going to find it frustrating to be a middle manager. And if you're naturally conventional-minded, you're going to be sailing into a headwind if you try to do original research.
People are often mistaken about where they fall on the spectrum from conventional- to independent-minded. Conventional-minded people don't like to think of themselves as conventional-minded. By the time they reach adulthood, most people know roughly how smart they are (in the narrow sense of ability to solve pre-set problems), because they're constantly being tested and ranked according to it. But schools generally ignore independent-mindedness, except to the extent they try to suppress it. So we don't get anything like the same kind of feedback about how independent-minded we are.
The conventional-minded are often fooled by the strength of their opinions into believing that they're independent-minded. But strong convictions are not a sign of independent-mindedness. Rather the opposite.
Paul Graham's suggestion on how to practice independent mindedness:
- Ignore conventional beliefs. It is hard to be a conformist if you don't know what you are supposed to confirm to. A common technique practiced by nerds.
- Surround yourself with others who are independent minded. Surrounding yourself with conventional thinkers will yield conventional thinking while surrounding yourself with independent minded will yield surprises.
- Cultivating conversations from people with different views will lead to multi-disciplinary thinking which allows you to import ideas from one to another.
- Reading history can influence time and space. Focusing not only on what happened, but try to get into the heads of people who lived in the past (hard to do however).
- Cultivate an attitude of skepticism. When you hear someone say something, stop and ask yourself “Is that true?”
- Stand back and watch how other people get their ideas. When you stand back at a sufficient distance, you can see ideas spreading through groups of people like waves. The best place to find undiscovered ideas is where no one else is looking.
There are 3 components of independent mindedness: fastidiousness about truth, resistance to being told what to think, and curiosity.
- Being fastidiousness about truth by using degree of beliefs.
For most people, degree of belief rushes unexamined toward the extremes: the unlikely becomes impossible, and the probable becomes certain. To the independent-minded, this seems unpardonably sloppy. They're willing to have anything in their heads, from highly speculative hypotheses to (apparent) tautologies, but on subjects they care about, everything has to be labelled with a carefully considered degree of belief.
- Resistance to being told what to think.
The big mistake people make about it is to think of it as a merely negative quality. The language we use reinforces that idea. You're unconventional. You don't care what other people think. But it's not just a kind of immunity. In the most independent-minded people, the desire not to be told what to think is a positive force. It's not mere skepticism, but an active delight in ideas that subvert the conventional wisdom, the more counterintuitive the better. Think how often your reaction to a novel idea is to laugh. I don't think it's because novel ideas are funny per se, but because novelty and humor share a certain kind of surprisingness. But while not identical, the two are close enough that there is a definite correlation between having a sense of humor and being independent-minded — just as there is between being humorless and being conventional-minded.
- Curiosity.
To the extent that we can give a brief answer to the question of where novel ideas come from, it's curiosity. That's what people are usually feeling before having them. Everyone I know who's independent-minded is deeply curious, and everyone I know who's conventional-minded isn't. If you're sufficiently curious, you don't need to clear space in your brain, because the new ideas you discover will push out the conventional ones you acquired by default.
Selective skepticism
There is skepticism as a permanent attitude and there is selective skepticism. A distinction between both is necessary. Selective skepticism is necessary in sound reasoning and discovery of truth. But being permanent skeptics can damage our perception of the real-world.
We shouldn't respond everything with doubt. There are situations where we should use selective skepticism. Selective skepticism is a useful tool when investigating the truth. It is useful to find enough information to validate a hypothesis or an argument. We should be reluctant to accept any conclusions at face value. Especially when a premise is questionable. Or a premise is being made by a questionable individual. This kind of healthy skepticism is necessary.
But skepticism as a permanent attitude can impair our perception of the real-world. Someone with this view will refuse to accept any sound reasoning. Or fail to understand the reasoning process. The extreme skeptic will claim there is no standard for sound reasoning so he or she will reject any truth. The whole purpose of logic is to discover the truth. It can be deadly if an individual does not bother to search for truth.
So, what should we do? Besides, being a selective skeptic, we can strive to be an optimist. But be aware of naive optimism. A naive optimist is someone who makes positive estimates without sufficient evidence. This represents an illogical position because a naive optimist acts out of prejudice. Their mind is already made up about a particular matter before they have engaged in other alternatives. Being a naive optimist clouds our observation if we ignore reality.
Embrace reality and seek to improve it. We can fix problems by keeping our minds open to various possibilities. A narrow-minded person will not consider alternatives because they do not meet their assumptions. An open-minded person will seek all possible alternatives and relevant information.
Being a permanent skeptic, naive optimist, or narrow-minded will cloud our observations. So what must we do? Do what scientists do: strive for objectivity. Scientists try to describe the world as it is, not as they want it to be. Selective skeptics will seek to answer whys and hows questions by using method of scientific integrity.
A sound reasoning can eliminate all prejudices by deploying selective skepticism in necessary situations.
Selective skepticism and sound reasoning can eliminate all prejudices in necessary situations.
There are in fact two things: science and opinion; the former begets knowledge, the latter ignorance. — Hippocrates
It does not make any difference how beautiful your guess is. It does not make any difference how smart you are, who made the guess, or what his name is—if it disagrees with experiment it is wrong. — Richard Feynman
Sit down before facts like a child, and be prepared to give up every preconceived Notion, follow humbly wherever and to whatever abysses Nature leads, or shall learn nothing. — Thomas Henry Huxley
Avoid tribes
In modern culture, we all associate ourselves to a certain tribe. Primitive humans would not be surprised to see this phenomenon today. This has been going on since ancient times.
Ideologies (ideas) become part of who we are. People get invested in their ideologies, especially if they get invested publicly and identify with their own ideologies. So there are many forces against changing your mind. Flip-flopping is a bad word to people. It shouldn't be. Within sciences, people who give up and change their mind get good points. It's a rare quality of a good scientist, but it's an esteemed one.
Being tribal causes intense ideologies. Intense ideologies cabbages up one’s mind. You start out as a kid with orthodox ideologies, you keep pounding on, gradually ruining your mind. Preachers will keep preaching their views. It happens daily, in every corner of life. The only core ideology is to not get hung up on what you already know or believe in. Listen to both sides because everyone comes from different experiences.
The solution to prevent intense ideologies is to get involved in more of tribal ideologies, not avoid them. Primarily, ego gets in the way because we think we know what is right and wrong. Staying neutral is what many choose but the world is not neutral. This is immensely powerful from an aspect of social learning. Tribes are schools of storytelling, connection, sense making, evolution, persuasion, human behavior and many other things. If any of these things are useful to you, you have to get involved. You can't learn these things from books or any other platform.
Examples of tribes include scientology, crossfit, blockchain, church, religion, etc. The way to free yourself from the control of an entity is to keep researching from the source of truth. At the core of tribes are usually patterns to be found around.
There are two things that are distilled in our society to prevent us from getting involved—institutions and ego (confirmation bias). Institutions like school, work or religion prevent us from thinking broadly. Second, ego gets in the way because we are so married to our own ideologies. If you really want to learn, join these tribes and exit.
Progressive enrichment of tribe membership should be everyone's goal. This allows us to think and learn incrementally.
Latticework of mental models
Use mental models to ask the right questions. You’ll learn to disassemble and reassemble ideas in such a way that they form something new from something old. Address and assess differing views as a means to form your own conclusions. You can use mental models as a guide book to your learning, rather than as a rule book.
Read widely and deeply, drawing lines between many disciplines and concepts so that the principles that apply to one can benefit you in another. For example, engineering principles can be applied to economics and vice versa. Independent thinkers approach a high-level of abstract thinking that allows them to draw upon their breadth of learning and reach their own novel solutions and ideas.
It is easy to pay homage to Charlie Munger’s widely-lauded latticework of mental models, but when you live it, you’ll see why he is right. Knowing the key drivers and major ideas from a variety of fields is a huge source of leverage. It is difficult to study broadly and deeply, but the two are not mutually exclusive.
Mental models will broaden your thinking so that you can make wise and informed decisions. Modern education systems hinder students when it comes to approaching problems from a broad, multidisciplinary perspective. Mental Models will help you gain that perspective and a basis for broad rational thinking.
Questions
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:
- At the level of semantics, a question is defined by its ability to establish a set of logically possible answers.
- At the level of pragmatics, a question is an illocutionary category of speech act which seeks to obtain information from the addressee.
- 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 approach to questioning
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.
- Socrates' interlocutor asserts a thesis, for example, “Courage is endurance of the soul.”
- Socrates decides whether the thesis is false and targets for refutation.
- Socrates secures his interlocutor’s agreement to further premises, for example “Courage is a fine thing” and “Ignorant endurance is not a fine thing.”
- 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.”
- 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 was 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.
- Sandwich framework
- 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
References
- Think by Paul Graham
- Great work by Paul Graham
- Identity by Paul Graham
- Hamming by Paul Graham
- ECW by Paul Graham
- Essay by Paul Graham
- Solitude & Leadership
- Critical Thinking In The 21st Century
- Scoratic Method
- Timeful Advice
- Tools To Improve Critical Thinking
- How To Make Strong Arguments
- Hill by Edward Tufte by Edward Tufte
- Determination by Paul Graham by Paul Graham
- Peter Attia Series by Peter Attia
- How to research at the MIT Lab
- Aristotle work on Logic
- 1984 by George Orwell
- A Brave New World by Aldous Huxley
- Being Logical: A Guide to Good Thinking by Dennis Q. McInerny
- Seeking Wisdom, From Darwin To Munger by Peter Bevelin
- Richard Feynman lectures
- Richard W Hamming lectures