Looking back, what's one decision you made that was a leap of faith? How did it shape where you are today?

Have you ever had a mentor, and what was the most important thing they taught you?

What behavior or trait immediately makes you respect someone?

If you could instantly bankrupt any person, company, country, or organization, who would it be?

What's the worst advice you've ever been given?

If you could witness any event from the past, present, or future, what would it be and why?

What would you consider to be a 'dream job', and how close is your current job to that ideal?

Can you share an instance where your first impression of someone was completely wrong?

Thinking about your current #1 goal, what makes you optimistic you'll achieve it?

What thoughts distract you when you’re trying to get to sleep?

Where do you feel you're improving the most?

What is the most memorable meal you've ever had? (It can be good or bad.) What made it so memorable?

What's your most common feeling lately?

If you could pick a new first name for yourself, what name would you choose and why?

Do you have a best year of your life? A worst?

What's your favorite non valuable item you'll keep to the grave?

What was the sickest you ever got, as a child?

What's your favorite quote and why?

How do you show someone you care about them?

What does "success" mean to you, and how has that definition evolved over time?

What is something other people admire about you?

What’s one of your earliest memories of earning money?

What do you plan to learn in the coming days?

Has your gut feeling or intuition about someone or something ever been wrong?

If you could have any mythical creature as a pet, which one would you choose?

What color describes your mood today?

What is one thing you're tired of explaining to people?

What do you consider as red flags in a potential friendship?

Who here is is most likely to establish a scientific law?

What talent of yours do you consider to be inherent, like an advantage you were born with?

Is there any aspect of your identity you sometimes feel you must suppress or amplify in certain social settings?

What one thing (something you made, something you did, something you contributed to) would you like to be remembered by?

How authentically do you feel you represent yourself to others?

If you had the power to completely solve one social or political issue affecting the world today, which would you choose?

If you could know for certain the answer to any question, what would that question be?

What's the most important lesson a friend has taught you?

If you could have dinner with any person, living or deceased, who would it be and why?

What's some surprising feedback you recently received?

What's something other people commonly do that you avoid, and are proud of doing so?

How would you describe your approach to your career so far?

Who is someone you think about a lot, that isn't thinking about you nearly as much? What do you make of this?

Do you believe in second chances?

What's a time when you were extremely underprepared for the task or situation at hand?

If you could level up any aspect of yourself (i.e., strength, intelligence, charisma, etc.) but you had to decrease another aspect of yourself by the same amount, what aspects would you level up and sacrifice?

What made you happy today?

Is there a behavior or pattern you keep falling into that hurts yourself?

What outfit makes you feel powerful, smart, or capable?

Have you ever turned down an opportunity, then came to later regret that decision?

What's something from your childhood that you think no one else could relate to?

What behavior or trait immediately makes you trust someone?

Explain your current feelings in life to a 3 year old.

What's something people are surprised to learn about you?

What's the most important lesson you've learned about leadership?

What does love mean to you?

What's something good that recently happened to you?

Who is your favorite philosopher or thinker, and what influence have they had on you?

What do you consider as red flags in a potential romantic relationship?

What's a standout moment where you felt excited recently?

What's something that will make you smile every time?

What's your go-to productivity hack?

Are you currently holding a grudge against anyone?

Imagine you woke up with the ability to speak every language fluently; how would you use this power first?

What are you most proud of right now?

How can you take better care of yourself? How will you make that happen?

What is the most important quality you look for in a friend?

Which childhood book or story influenced you the most?

What's something you recently taught yourself?

What's currently worrying you?

What is the most fun you have had recently?

If you could intervene during any historic event, changing history, what would it be? How would things unfold differently?

Do you feel challenged enough at work?

What's the most significant risk you've taken in your career, and how did it turn out?

Is there anything you think the previous generation did better than your generation?

Who here is most likely to own 20 house plants and give each of them unique names?

Where do you wish you had grown up?

What's the quirkiest habit you have that you're willing to admit?

What would you like to thank yourself for right now?

What's a recent personal growth moment you've experienced?

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

What do you consider as red flags in a potential employer or boss?

Is there anything important you've been putting off? If so, why?

What's the most fun you recently had? What did you do, and who were you with?

What's the most unusual food you've ever tried, and would you eat it again?

What is your favorite word and why?

If you were reincarnated as an animal based on your personality, what animal do you think you would come back as?

If you had the power of perfect memory recall, what’s the first memory you’d revisit?

If you could alter one decision you made in your early 20s, what would it be?

What's something you recently came across that gave you hope or inspiration?

How have you been lately?

What's a "red flag" in a relationship or friendship?

What's an unpopular or controversial opinion that you hold?

What's a great piece of advice you recently received? Who was it from?

What's the best career advice you've ever received?

Who here is is most likely to have the most children?

Who in life has inspired you the most?

What does your dream home look like?

What's the best lesson you've learned from a difficult situation?

What are 3 words you'd used to describe how you currently feel?

If you could only use five words, how would you describe yourself?

What would brighten your day today?