What is an irrational fear you have?

What was your biggest win lately?

What would make you feel like "you made it"?

How much of your decision to stay in your current job is influenced by comfort and fear versus ambition and fulfillment?

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

What's a fear or insecurity you're working through?

If your life was a story, what chapter would you currently be in, and what would its title be?

What advice would you give about maintaining long-lasting relationships?

What's a habit you're trying to develop or break?

What's something you are really into right now?

What kind of person do you want to be?

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

How’s your heart today?

If you had the power to talk to animals, which species would you chat with first?

What’s something at the top of your to-do list?

What do you think is the best place or way to meet a signifcant other?

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

What’s something that made you laugh recently?

What's something you recently learned?

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

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

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

Who had the most significant impact on your career and why?

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

What embarrassing memory will forever be seared in your memory?

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

What's a hobby you've always wanted to try?

How do you measure the impact of your work on society?

Is there anyone close in your life that perceives you differently than you perceive yourself?

If you could have a superpower that helps you in your current job, what would it be?

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

How do you prioritize your goals and desires in life?

If you could have witnessed one event from your family history, what would it be?

Where do you wish you had grown up?

When was the last time you had a difficult conversation? Who was it with, and how did it go?

What do you think is the most significant impact individuals can make in the world today?

What single event or decision do you think most affected the rest of your life? Was there a turning point in your life?

What is your favorite word and why?

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

What is your most terrible memory?

What makes you optimistic about the future?

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

What do you feel like you’re really good at?

How do you show someone you care about them?

Who in your life would you trust with your deepest secret?

How has your perspective on the world changed in the last five years?

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

What have you been dreaming of eating lately?

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

What is something you've become increasingly interested in the more you've learned about it over time?

Have you attended any interesting work-related seminars or workshops lately?

What's your favorite way to relax these days?

What was your first job, and what did it teach you?

Name one thing that stresses you out without fail.

What do you think all happy people have in common?

What do you wish people would talk more about right now?

Who's life do you think you've impacted the most?

Are human desires endless, and can a society exist without wanting more?

What stopped you from following, or encouraged you to follow, your childhood passion?

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

You can know when you die or how you die. Which do you choose?

When was the last time you cried and why?

Explain your job to a 3 year old.

You will be granted supernatural ability in one of your five sense (sight, smell, taste, hearing). Which would you choose, and why?

What is the most powerful habit, good or bad, in your life right now?

What fictional character would you most like to have as a mentor?

If you had to choose a theme song for your life, what would it be?

If you could teach someone just one thing about how to be in a good relationship, what would it be?

What self-limiting beliefs do you currently hold?

What's your favorite article of clothing you own?

What quality do you most appreciate about your partner?

What's a memorable lesson you've learned from a mistake you've made?

If you could have any author write your life story, who would you choose?

What do you take for granted?

How do you feel about your relationship with your father?

What was the best birthday gift you ever got?

What do you think is the most important quality of human civiliation for its continued survival?

What's a deep question you often ask yourself?

What is your most regretful purchase?

What's a belief you held strongly that you changed your mind about?

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

What's something you wish people asked you about more often?

If you could be invisible, but it would mean being permanently invisible, would you want to be this way?

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

Who here is is most likely to eat cat food?

What's a surprising hobby you enjoy?

It's "Freaky Friday". You wake up in someone else's body for a day. Who would you like to wake up us, and have them inhabit your body instead?

You just became a new member of the Spice Girls. What's Spice name do you create for yourself?

How do you resolve conflict with the closest people in your life?

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

How well do you receive feedback?

What is one commitment you've made to showing up differently in a particular relationship of yours?

What tools or apps do you find indispensable for your work?

Who is someone that you recently issued a genuine apology, and what was it for?

What's something you'd like to do, but have a hard time acting on?

When was the last time you experienced stillness and wonder?

Which is more important, nature or nurture?

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

What life experience has shaped you the most, and in what way?

How do you approach networking, and have you had any success stories?