Jackie's "Real Conversation Questions"
- What was the best part of your day? Week? Year?
- Tell me something about yourself that you wouldn’t mention the first time you met someone.
- What’s the best gift you’ve ever given or received?
- What’s your aesthetic? How did you arrive at it?
- Do you have any nicknames? If so, what’s the story behind them?
- When was the last time you did something for the first time?
- What is your latest discovery about or in the city in which you live?
- Would you like to be famous? In what way or for what?
- What’s your best memory from high school?
- What’s the best compliment you’ve ever received?
- What would constitute a perfect day for you?
- If you could gain any quality or ability, what would it be?
- Give the choice of anyone in the world, who would you want as a dinner guest?
- What’s a work (book, movie, etc.) that shaped the person you are today?
- Tell me about a time that you were spontaneous.
- What’s the most illegal act you’ve ever done and are comfortable sharing?
- When did you last leave your comfort zone?
- What was your last epiphany?
- Would you pick a different career path if you did life again?
- What’s one specific fact about what it’s like to live in your particular body?
- What was your most memorable first kiss?
- With whom do you have the best connection in your family? Why?
- What’s the most memorable date you’ve ever had?
- Tell me about your biggest crush.
- Who do you respect most in your life? Why?
- Do you have an enemy? If so, why?
- How did your best friend become your best friend?
- How did your parents’ values shape your career choice?
- What do you value most in a friendship?
- For what in the past year do you feel most grateful?
- Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?
- What’s your greatest accomplishment?
- What’s an embarrassing moment in your life that you still remember?
- What does it mean to you to live a good life?
- What experience have you had that made you a more compassionate person?
- When was the last time you faced a big ethical dilemma? What did you do?
- What brings you joy?
- Do you feel fulfilled by your work? Why or why not?
- When was the last time you were really proud of yourself?
- What’s the most important self-discovery you made about yourself in the past year?
- What’s an experience in your past that really shaped your worldview? Why?
- How do you hope you’ll change as a person in the future?
- What excites you most about the world in which we live?
- What frustrates you most about the world in which we live?
- What are three of your personal qualities of which you’re most proud?
- What have you always wanted in romantic relationships but never had?
- If you were to die with no warning, what would you most regret not telling someone? Why haven’t you told them yet?
- What liberates you?
- Do you have enough love and affection in your life? Why or why not?
- Tell me about your hardest breakup and why it happened.
- What were the major tipping points in your life that shaped your identity most? How did they affect you?
- What’s your biggest insecurity?
- Tell me about a time that someone really hurt you.
- Tell me about a time that you really hurt someone else.
- What makes you look down on other people?
- What do you think makes other people look down on you?
- Imagine you’re a parent. How would you raise your child differently from the way you were raised?
- How do you feel about your relationship with your mother?
- How do you feel about your relationship with your father?
- Are your passions, morals, ideals, etc., consistent with the way you live your life? If not, why not?
- How do you assign self-worth?
- If you knew that, in one year, you would die suddenly, would you change anything about the way you’re living now? Why?
- What life experience made you grow the most?
- What’s your most treasured memory?
- Are you content? Why or why not?
- If you could change one decision you made in your life, what would it be? Why?
- When did you last cry in front of another person? By yourself?
- What’s the most depressed you’ve ever been? What happened?
- What’s the hardest experience you’ve ever had to undergo?
- What made you feel most insecure in your childhood?
- What’s your biggest regret?
- What’s a major problem you’re facing in your life right now?
- What do you see as your responsibilities to the world? Your loved ones? Yourself?
- What are three of your personal qualities of which you’re most ashamed?
- Where in your life are you giving more than you’re taking? What about taking more than you’re giving?
Lama's "Skip the Small Talk"
- If you were going to be frozen tomorrow for a one-way 1000-year interstellar voyage, what would you most want to communicate (and to whom) before you leave?
- What do you think you’re most likely to regret on your deathbed?
- What do you miss most about your past that could be recreated today?
- What’s the most important thing to remember daily that you haven’t been able to?
- What help could you most use that you haven’t asked for?
- What is your one piece of advice to everyone here?
- What was the last thing you fell in love with?
- When was the last time you felt unbounded optimism?
- Who was the last person you felt inspired by?
- What simple thing still blows your mind?
- What sparked your curiosity in whatever you’re most curious about now?
- What’s the most useful concept you have that doesn’t have a name?
- What’s something you believe but can’t defend?
- What taste do you have that most people don’t have, where does it come from, and how has it helped you?
- What is your most radical belief?
- Do you think it’s more important to follow the “written” rules or the “unwritten” rules? What is one unwritten rule that you’ve learned?
- What is the most significant thing you’ve changed your mind on in the last year? Why did you change your mind about it?
- Which fictional character would be the most boring to meet in real life?
- What’s the closest thing to real magic?
- If you could know the absolute and total truth to one question, what question would you ask?
- Which question can you ask to find out the most about a person?
- What do you want your epitaph to be?
- There are two types of people in this world. What are the two types?
- What is something you are certain you’ll never experience?
- Who is/was your most interesting friend?
- What small gesture from a stranger made a big impact on you?
- If you had a clock that would countdown to any one event of your choosing, what event would you want it to count down?
- What are three of the most significant numbers in your life?
- Which of your personality traits has been the most useful?
- Imagine you have a closet full of robots at the ready. Which of your various obligations would you assign to a robot? Which tasks and activities would you keep to yourself, because you enjoy them too much to delegate them to even a robot who is better than you?
- What is the best measurement of how an idea is absorbed into culture?
- Do you think you’re undervalued as a person? If so, why?
- Why are some people so addictive?
- What color best describes your personality?
Best questions = Care about other person when thinking of a Q and ask in that context.
Worst question = ask via curiosity like they are a slot machine
"Tell me your weaknesses" vs "what would make you stronger?"
What are examples of “better questions”?
“How are you? —> “What’s on your mind lately?” “Are you happy?” —> “Are you proud of yourself?” “Are you close to your family” —> “How has your family affected you?”
Better questions avoid binary responses (good/bad, yes/no, etc).
- Asking questions that border along the obtuse or nonsensical, just to see how people interpret them.
- What's been exciting (to) you lately?
- One idea that's stuck with me lately is: "All thinking is regional thinking." How has the place you grew up shaped your thought?
- What do you think is your most absurd belief?
- What is something that people mistake or misunderstand about $DOMAIN_OF_EXERTISE
- What's a silly thing you've done in the past year that you're most proud of?
- What's a belief you hold that's closest to a conspiracy theory?