Questions

If today was your last day, what would you have most regretted not doing yet?

If today was your last day, what would you of have been most proud of?

What’s something most people see as black or white that you think they should be seeing as gray? Is there something you’re seeing as black and white but think there may be a gray area to consider?

if you could only have 3 of your 5 senses, which would they be?

What are the two absolute luckiest things that have ever happened to you?

Do you have an area of interest that you would likely (95%+ confidence) still be interested in in your old age? (80s, 90s, beyond)

What do you want written on your tombstone?

If your life was a dashboard what would be the key stat/ measure?

Is there something that can’t hurt you and you’re still afraid of?

Let’s say we were going to start a village. What would you bring to the table? Why?

What’s the biggest commitment you’ve ever made?

What's the hardest challenge you’re working on yourself?

What’s the best worst thing you’ve ever done?

Could you teach me something complicated I don’t know? (Sergey’s fav interview q. Google)

What do you know now in a deeper way than you knew it before?

What tittle would you give this chapter in your life?

Whats an unusual habit you have?

What’s something Google doesn’t know about you?

What’s the worst advice you hear often in your field?

Do you have any favorite failures? Any failures that in hindsight led to incredible things?

In what ways has your personality served you in achieving dreams vs. held you back?

What are the most worth while investments you’ve ever made? This can be time, energy, money...

If you could pick one class that would be mandatory for everyone, what would it teach? At what grade level(s) would it be mandatory?

Do you have a hunge of how you’re going to die?

What do you really want to do, and how does that differ from what you feel you should do?

What were you like as a child? And what do you think the child version of you would think of you you’ve become today?

Outside of work, what do you feel like is working in your life right now? What isn’t?

If you had to be a drink which and why?

If you could have one gigantic billboard anywhere with anything on it—metaphorically speaking, getting a message out to millions or billions—what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)

What’s a question I didn’t ask that you wish I’d asked?

What lesson did you have to learn "the hard way"? How can you help others avoid your mistake?

How do you think of luck? What about luck in correlation with success?

Locus of control: what percentage do you think yours in internal vs external? What about for good things that happen? Bad things?

Do you think the end or the means are more important?

Complete this statement: “I lose track of time when...”

What have you done in the past 3 months that makes you feel proud?

As you have gotten older, what has become more important and less important to you?

What are some challenges that you’ve had to overcome in your life?

If you could study with any expert in the world, who would you work with and what would you study?

If you could invite 3 people (living or dead) to your home for dinner, who would they be and why?

Do you think the future would stay the same if you were told the future? Or would you act differently and it’d change as a result.

What’s something you think is truly worth doing, whether you fail or succeed?

How would you like things to be different in your life?

What’s missing from your life that you could add with effort?

If you could go back and tell your 20yr old self ‘this is where you are going to be and this is what it took to get here,’ do you think you’d still do it?

What is something you want to remind yourself of in 10 yrs?

Can humans be satisfied being taken care of just like a family dog? (When robots/ AI can do everything for us)

Suppose that you go to bed tonight and sleep well. Sometime, in the middle of the night, while you are sleeping, a miracle happens and all the troubles you have are resolved. When you wake up in the morning, what’s the __first small sign__ you’d see that would make you think, ‘Well, something must have happened- the problem is gone!’?

Prod for more specifics ‘what will you do instead?’It doesn’t ask you to describe the miracle itself; it asks you to identify the tangible signs that the miracle happened.Focus on the first hits of the miracle to avoid answers that are overly grand and unattainable.When was the last time you saw a little bit of the miracle, even just for a short time?

Do you think feelings can be false?

What song would play anytime you walked into a room?

If you were the dean of admissions at the world’s top university, what would be your decision rule?

What's your biggest failure, and what can I learn from it?

If every person on the planet had to listen to you for 5 minutes, what would you say?

What are three negative things about ya?

If you could give credit or thanks to one person in your life that you don’t give enough credit or thanks to, who would that be?

If you were to die tomorrow and you could only leave your children one paragraph worth of all of the knowledge you’ve accumulated over the years, what would it say?

If you were to get kicked out of the company what do you think the new CEO/____ would do? (A more beautiful question book)

What if your company didn’t exist? (Think about the industry and your role in it without the luggage or sunk costs) - useful if at any point in the future you see the possibility that the core business might slow down Who would miss us? Help clarify who your most important customers are and what your real purpose is. What should we stop doing?

If we were to pop a bottle of Champaign a year from today. What would we be celebrating?

(After response) in order to achieve that is there anything you need to solve or overcome?

Given the choice of anyone in the world, whom would you want as a dinner guest?

What would constitute a “perfect” day for you?

If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?

What was the last meaningful “thank you” that you received?

What are a few ways in which you express your gratitude?

What are you most proud of? / What is your proudest moment? Why?

What is something that can instantly turn your bad day into a good one?

Complete this sentence “I wish I had someone with whom I could share...”

Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

What fun topic could you give a short presentation about with no preparation?

Think about yourself one year ago. What’s one thing that’s changed since then?

What would you consider a defining moment in your life?

What do you value most in a friendship?

Human memory has been shown to be incredibly unreliable. With that in mind, how do you know which of your memories are genuine and which have been altered or made up?

What is your most treasured memory?

If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

What does friendship mean to you?

If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

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?

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?

What do you want to want?

If you had to give a TED talk on a subject/ topic you’re not know for, what would it be?

When did you last cry in front of another person? By yourself?

If there was a movie about your life what would it be called?

What’s the greatest lesson you’ve had to UN-learn in the past year?

If every day someone was filming everything you did and in the evening you and your loved ones had to watch it all. Would you still do the same things?

Do you think everyone is always doing their best?

Do you think painful emotions should be ignored?

Do you think there’s a right way to feel in every situation?

Do you think you can control the way you feel?

Can time exists without language?

If we all shared the same values/ morals, would we need government?

How would you like people to remember you?

If people didn’t have to work, because AI and machines are doing everything and there’s so much abundance that everything is free. Universal basic income is going to become a necessity. Then how will people have meaning? a lot of people derive their meaning from their employment, so if you aren’t needed, there’s no need for your labor. What’s the meaning? Do you have meaning? Do you feel useless?

If your life was a book, would you read it?

If you could live indefinitely, would you?

What’s your conversational landmine? (What gets you going)

Which item on your bucket list will be the easiest to tackle? The most difficult?

What’s your definition of success? What does it look like?

If you could spend a day in someone else’s shoes, whose would they be? Why?

What's one thing your mother/father taught you that completely changed your life?

What's one of your favorite memories?

Imagine that a spell of unanimity has been cast on you from now on for the rest of your life no one would know what you do, no one would know how much money you make, how successful you are, you and you alone would know. In such a world of unanimity what would you do?

- What we’re passionate about without worrying about other peoples expectations of you or what they think of you.

What's one thing about you that surprises people?

If you could instantly become an expert in something, what would it be?

If you could wake up tomorrow having gained any one quality or ability, what would it be?

For what in your life do you feel most grateful?

Name three things you are thankful for at this time in your life.

What’s the best piece of advice you’ve ever been given?

If you didn’t have to sleep, what would you do with the extra time?

What’s your guilty pleasure?

Has anything ever happened to you that you could not, and cannot, explain?

If forensic analysts confiscated your calendar and email records and web browsing history for the past 6 months, what would they conclude are your priorities?

If we weren’t to talk for the next 3yrs and I called you and asked for a life update and you’ve achieved everything you could have wished for, what would you tell me? “Holly shit! You won’t believe what just happened...” (Dom)

What would you do if you received two life changing phone calls. In the first call, you’d learn that you’d inherited $20m, no strings attached. The second call would inform you that, due to a rare and incurable disease, you had only 10 yrs left to live. What would you differently, and, in particular, what would you stop doing?

Do you feel lucky in life?

If you repeat the actions (/ habits) that you performed today for the next 10 years, would you be pleased with the results?

What’s the most unbelievable-but-true thing that’s ever happened to you?

If money were not an issue, what would you be doing right now?

What's something you wish you had done years earlier?

What words of advice would you give your younger self?

How do you clear your mind after a long day?

If you had a free round-trip airplane ticket to anywhere in the world, where would you go?

Who has been the greatest influence in your life? How?

What's the most creative thing you've ever done?

Which founders or startups do you most admire?

What's your super power? or If you could have any superpower, what would you pick?

What’s your favorite quote? / Your motto?

What aspects of your work are you most passionate about?

What was the most impactful class you took in school?

If you could know what someone was thinking, how do you think it’d be presented to you?

Tell me the story of your life and the decisions you made along the way and why you made them.

Video games are becoming so real that in the future it will be hard to tell the difference between being in the game and in real life. Who’s to say this hasn’t already happened in the past and that we aren’t in one of those games now. How would you know?

What’s the quirkiest thing about the town where you grew up?

What’s the craziest way you’ve ever traveled? Hot-air balloon, camel, blimp… ?

If you could change one thing about yourself, what would it be?

Do you take any classes or practice a particular hobby? Would you like to?

In a world without death/ heaven/ hell/ reincarnation- what will happen to religions?

If people were to live to 160yrs old easily. How do you think it will impact family structures/ relationships? What about careers?

If you could win an olympic medal for any sport, real or fake, what would it be?

Have you had a near death experience? How did it affect the direction of your life?

If you could change your name, what would it be?

What movie or TV show tittle best describes your week?

If you had to eat one thing for every meal going forward, what would you eat?

Who, or what, was your biggest teacher?

What’s something you’ve done that made you feel extreme happiness?

How can someone win a gold star with you?

What culture, other than your own, do you find most fascinating?

What qualities do you value in the people with whom you spend time?

Would you like to be famous? In what way?

For what would you be famous?

What does your dream day look like?

If you had to choose only 3 adjectives to describe yourself, which would you choose?

How many jelly beans could fit into this room right now?

If your significant other died and was reincarnated into another body. How would you know it was them? What question would you ask to know?

Who have I been over the last few weeks / months? (give 3 adjectives)

Follow up with: Who do I need to be in order to get to where I want to get? (Give one adjective)

What are the 3 things you want to achieve on a personal /business level that would give you a tremendous feeling of success?

What are the relationships you want to have?

What are 3 genie/magic goals you wish (wherefore you have nothing to do for /to have it/ to keep it)?

What are the experiences you want to have before you leave the planet,

What are your 3 naughty goals (goals you should't have)?

What goals SHOULD you do by the end of the year (SHOULD GOALS)?

What are your top 3 OTHER PEOPLE's goals?

What are your growth goals - How do you want to grow?

What do you want to contribute to the planet?

Significance Goals - What to you want to be known/be remembered for?

What are your ANTI-GOALS - What do you never want do EVER again?

What's your IMPOSSIBLE Goal?

What do you need to simplify (instead of what should you do) - Less but better?

What are you prepared to struggle for?

Focus question : what's the one thing you should do that would make all the other goals easier/unnecessary?

What have you accomplished that you're proud of, but would be unimpressive to anyone else?

What’s your communication style? How does it affect the people around you?

In the future, which one of these things do you think we’ll look back on and think was the most barbaric? manual driving, labeling based on gender, governing with a two-party system, poor health care, factory-style education, destroying the environment, war and eating meat

Describe your “average” day. What are your rituals/routines?

Complete this statement: My favourite time of the day is...

What are three things you believe you need in order to be happy?

How would you spend 6 hours with your best friend?

What do you daydream about?

If you could "stop the clock" and live forever at a particular age, what age would it be and why?

If you could outsource one of your daily tasks, what would it be and why?

What would you say is your greatest strength?

What is one word your best friend would use to describe you?

How would your best friend describe you in 2 words?

What is something you would like to learn to do?

Imagine that tonight there is a party honoring you on your 80th birthday. What are five brief things you would like family and close friends to say about you?

What are 3 things you would like to be doing in three years?

What do you look forward to every night? Why?

If you had to move and could only take 3 things with you, what would they be?

Describe the most unpleasant job you ever had to do.

What did you want to be when you were growing up?

What has been one of your happiest moments?

If your closest friend wrote a book about your life, what would the title be?

What are you excited about right now?

Share an interesting fact about yourself that not many people would know.

What are you working on?

What are some ways that you reconnect with yourself?

Who is the first person that comes to mind when you hear the word "successful"? Why?

What is one thing you couldn't live without?

If you could start a charitable organization, what would you name it and what would the cause be?

Where would you like to retire, and why?

What was your first job?

What is one of your top business/ career achievements?

What is often your first thought upon waking?

What are 3 things you really value?

What's the most exciting thing you have ever done?

Any upcoming travel plans?

Are you a night owl or an early bird? Does it hurt or help you?

What brought you here?

How do you two know each other?

When you’re not working, how you like to spend your time?

What are you reading currently?

What is your favourite movie/documentary? Why?

What do you most hope to visit?

What is your most used emoji?

What’s the one thing you’re excited about that’s coming up in 2019?

What’s your favorite word?

What’s your favorite book?

What do you do to “reboot” so that the busyness and tech overload in your life does not result in burnout?

What’s your dream job?

Can you see yourself being stimulated and fulfilled on your current career path for the next five years?

What’s been on your mind lately?

Where is your happy place?

What energizes you/ brings you excitement?

What would you tell your future self?

What is the true measure of wealth / success?

What’s your favorite / most memorable child book / fable / story? how has that shaped you?

Think about the price and value you currently deliver. if you were to 10x that price, what would you deliver? what would you add?

If right now you couldn’t get new customers other than from your existing customers, how would your current customer experience change?

If you needed to provide more value than you currently are for 1/10th the price, what would you have to build that is free to replicate to deliver that value?

In as much precise detail as you see fit, how does your mind work?

What important truth do very few people agree with you on? - Zero to One

What, and who, is worth suffering for?

What would you stand for if you knew that nobody would judge you?

What would you do if you knew that nobody would judge you?

Do you think my name suits me? If so, why? If not, what name could I pull off?

If your life were a story, what would be the biggest plot twist?

When you were young did you imagine you would be where you are today?

- Share one prediction that came true and one that was way off

Tell me about a time you felt invincible

What is a lesson in your life that keeps repeating itself?

Has a compliment ever changed the way you think about yourself?

What is something so far out of your comfort zone that you wouldn't even consider trying it?

Are there any strangers you still remember?

If your closest friend wrote a book about your life, what would the title be?

What are 3 things you would like to be doing in three years?

Have you had a near death experience? How did it affect the direction of your life?

In order to take your company/life to the next level, what is one problem you need to solve?

If you could study with any expert in the world, who would you work with and what would you study?

How do you externalize your thoughts?

If you could know the absolute true answer to one question... what would the question be?

What’s your favorite saying?

Can there be thinking/creativity without language?

What is your serial killer trait?

What habits do you have that you hope you don’t pass on to your children?

What question do you rarely get, even though you’re thinking about the answer a lot?

What's a sacrifice you've made that i haven't acknowledged?

What are you hesitant to tell me?

Who is the most interesting person you've ever met?

Would you rather do what the best ____ does or the opposite of the 3 worse ______s you know?

What's the most surprising fun fact you've ever heard?

If you were able to ask an alien some questions, what would they be? 👽

What was the darkest time in your life and what was your road to recovery?

What do you think will be the greatest conversation you'll ever have? What's the greatest conversation you've ever had?

If you had to do a guest episode on a podcast with 1m+ listeners, who do you feel is the person you'd be most equipped to interview?

Who is someone who makes you nervous?

Which activities in your life are you minimizing that should be eliminated? Which activities do you need to savor and how can you best savor them?

How do you know if an idea is good?

What personality characteristics do you find most important in people?

When you think of the word “successful,” who’s the first person who comes to mind and why?

What is something you believe that other people think is insane?

What purchase of $100 or less has most positively impacted your life in the last 6 months?

What are your morning rituals? What do the first 60 mins of your day look like?

What obsessions do you explore on the evenings or weekends?

Do you have a quote you live your life by or think of often?

What is the worst advice you see or hear being dispensed in your world?

If you could have one gigantic billboard anywhere with anything on it, what would it say?

What advice would you give to your 20-, 25-, or 30-year old self? And please place where you were at the time, and what you were doing.

How has a failure, or apparent failure, set you up for later success? Or, do you have a favorite failure of yours?

What is something really weird or unsettling that happens to you on a regular basis?

What have you changed your mind about in the last few years? Why?

What do you believe is true, even though you can’t prove it?

Who is good at [skill or topic] despite being poorly built for it? Who’s good at this who shouldn’t be?

Who are the most controversial or unorthodox athletes or trainers in [skill or topic]? Why? What do you think of them?

Who are the most impressive lesser-known teachers?

What makes you different? Who trained you or influenced you?

Have you trained others to do this? Have they replicated your results?

What are the biggest mistakes and myths you see in [skill or topic] training? What are the biggest wastes of time?

What are your favorite instructional books or resources on the subject? If people had to teach themselves, what would you suggest they use?

If you were to train me for 12 weeks for a [skill or topic] competition and had a million dollars on the line, what would the training look like? What if I trained for 8 weeks?

How old would you be if you didn't know how old you are?

What old picture of yourself would be your album cover?

What do you know to be true today that you didn't know a year ago?

What are your biggest distractions that hinder your productivity?

If someone else described you, what do you think they'd say? Why?

If you could have any three things in the world, what would they be?

How can you feel more fulfilled in your life?

What's the best compliment you've received?

What are your best qualities?

If you couldn't fail, what would you do?

How do you show someone you love them?

What is one thing you want to overcome/conquer?

How would you behave if you were the best in the world at what you do?

When was the last time you did something for the first time?

On a scale of 1–10, how happy are you with your life today?

If <10: If your first answer was [answer + one], what would be different?

What’s keeping you busy?

What is the conventional wisdom that you disagree with?

Finish this sentence: "If you really knew me, you would know that I _ _ _ _ _ _”

What's something you feel guilty buying but love?

What is your one true question?

Imagine you’re back in high school and there’s a magic genie and he grants you one wish. The wish is that you can choose any student in that room beside yourself and you will receive 10% of all of the money they make for all of their lives. How would you choose that person? The prettiest, the smartest? the best player? how would you gauge that?

What do you think is the recipe for a magnetic personality / person?