Questions

For a while I kept a note of good questions to ask. A good chunk of these are likely sourced from an article on the internet, but I couldn’t find it during a cursory search. Therefore, as a disclaimer, I do not claim to be the source for any of these.

More Professional

What do people misunderstand about you?
What gives you energy and what depletes?
What’s a lesson you learned the hard way?
Tell me about a time you were mistaken.
Tell me about someone you’ve helped.
What’s the last book you read? Did it teach you any lessons?
What was your New Years resolution and how did that turn out?
What company would you invest $100,000 in?
Tell me about a time you changed your mind about something.
What are the three most important characteristics of this function? How would you stack rank yourself from strongest to least developed among these traits?
Tell me about your ideal next role. What characteristics does it have from a responsibility, team, and company culture perspective? What characteristics does it not have?
Tell me about the best and worst bosses you’ve ever had, specifically, in your career. What was the difference?
When was the last time you changed your mind about something important?
What’s one part of your previous company’s culture that you hope to bring to your next one? What one part do you hope to not find?
Tell me about a time you strongly disagreed with your manager. What did you do to convince them that you were right? What ultimately happened?
It’s a year in the future. What impact on the business have you made in the year since you’ve joined?
What gives your life meaning?
What motivates you to work?
How did you prepare for this interview?
What do you believe you can achieve with us personally or professionally that you can’t anywhere else in the world?
Looking back on the last five years of your career, what’s the highlight?
What are you really good at, but never want to do anymore?
What’s the difference between someone who’s great in your role versus someone who’s outstanding?
What’s something you’ve disagreed with over the past week?
What did you fail at this week?
Among the people you’ve worked with, who do you admire and why?
Tell me about a time you took unexpected initiative.
What’s something great about your current or previous job? Why?
For the last few companies you’ve been at, take me through: (i) When you left, why did you leave? (ii) When you joined the next one, why did you choose it?
Imagine yourself in three years. What do you hope will be different about you then compared to now?
What do you want to do differently in your next role?
Why don’t people like working with you?
If you didn’t have to sleep, what would you do with the extra time?
What’s the most important thing you’ve learned from a peer and how have you used that lesson in your day-to-day life?
Tell me about a time you really screwed something up. How did you handle it and how did you address the mistake?
Tell me about a time you made a mistake or failed at something. What did you learn from this experience? Can you give me two other examples?
When have you felt the lowest in your career? Did you realize how you felt in the moment? How did you respond?
What’s one misconception your coworkers have about you?
What are you better at than most anyone else? What’s your superpower and how will you leverage that to make an impact at this company?
If I were to go and speak to people who don’t think very highly of you, what would they say?
What’s one critical piece of feedback you’ve received that was really difficult to hear? Why was it difficult and what did you do with that information? What did you learn about yourself?
What was the last thing you nerded out on?
What are some things outside of work that you’re irrationally passionate about?
What’s the first job you had that’s not on your resume, and what did you learn from that experience?
Why shouldn’t we hire you?
What should our team be doing differently that could yield 10x improvement?
Teach me something.
If you were to take over as CEO of your current company tomorrow, and had to increase your company’s current rate of growth, what three areas you would invest in?
How would you build a product for people who are looking for an apartment?
What are 10 ways to speed up Domino’s pizza delivery?
What can I tell you about working here?
If you were in my shoes, what attributes would you look for in hiring for this role?
What have I not asked you that I should have?
Tell me about a time you went out of your way to help a coworker achieve a goal with no benefit to yourself.
What has to be true about this role, and about our company, for this to be a compelling opportunity for you?
Tell me about something you love doing that you’re terrible at and something you really don’t like doing that you’re great at.
Share one weakness that you are working on, and one weakness that you choose not to work on.
What’s an example of a time when you didn’t have the answer to something? What did you do? Looking back now, do you think there was a better/faster/easier path to the answer?
Tell me about a really difficult problem you faced, and how you attempted to resolve it.
What are your 5 non-negotiables for your next role?
Tell me about a time you broke a rule and why.
Could you tell me about a time when you worked on a project with an unclear objective?
In the interviewer debrief, what do you think we will say about you?
Why are you a risky hire?
What job would you be terrible at?
What do you want to do differently in your next role? (via)
Among the people you’ve worked with, who do you admire and why?
What’s something not many people know or care about that they should?
Who’s someone currently doing something that excites you?
What would you do if you were just getting out of high school now and going to take a gap year?
What excites you right now? What are you looking forward to?
Why did you choose your profession?
What are you currently reading?
How can I be most helpful to you right now?

More Personal

What’s something you didn’t like but you are glad happened?
What’s something you’ve lost that you still think about?
How are you useful?
What’s the greatest misperception others have about you?
What compliment do you wish you could receive about your work?
What would surprise me/everyone about you?
What would your life look like if it were easy?
What’s a story you’ve always wanted to tell?
If you could change one day in your life, what would it be?
What would your parents/friends say your strengths and weaknesses are?
What do you like and dislike about yourself?
If you could have any material possession, what would it be?
Tell me about a time you changed.
What do you regret not doing?
What lie do you tell most often?
What’s the most illegal thing you’ve done?
What keeps you up at night?
If you had a personal flag, what would be on it?
What’s the most immature thing that you do?
What’s the best thing about you?
What do you have doubts about?
Who has impressed you most with what they’ve accomplished?
What age do you wish you could permanently be?
What’s something you like to do the old-fashioned way?
What’s the best single day on the calendar?
What is the most annoying question that people ask you?
What is the most heartwarming thing you’ve ever seen?
What could you give a 40-minute presentation on with absolutely no preparation?
What’s worth spending more on to get the best?
What are you most looking forward to in the next 10 years?
Where is the most interesting place you’ve been?
What’s the best thing that happened to you last week?
If all jobs had the same pay and hours, what job would you like to have?
What quirks do you have?
How different was your life one year ago?
What’s the best way to start the day?
What do you hope never changes?
What movie title best describes your life?
What would you rate 10 / 10?
If you were dictator of a small island nation, what crazy dictator stuff would you do?
What is something you think everyone should do at least once in their lives?
Why did you decide to do the work you are doing now?
Where would you rather be from?
What are some things you’ve had to unlearn?
What are you looking forward to in the coming months
What one thing do you really want but can’t afford?
What website do you visit most often?
What are you most likely to become famous for?
What are you absolutely determined to do?
What do you wish you knew more about?
What question would you most like to know the answer to?
What question can you ask to find out the most about a person?
When was the last time you changed your opinion / belief about something major?
What was the best compliment you’ve received?
As the only human left on Earth, what would you do?
Who inspires you to be better?
What do you want your epitaph to be?
What did you think you would grow out of but haven’t?
In what situation or place would you feel the most out of place in?
What’s the dumbest thing you’ve done that actually turned out pretty well?
They say that everyone has a book in them. What would your book be about?
What is something you will NEVER do again?
What do you spend the most time thinking about?
What are some of the events in your life that made you who you are?
What do you wish your brain was better at doing?
There are two types of people in this world. What are the two types?
What is the strangest thing you have come across?
What is something you are certain you’ll never experience?
What dumb accomplishment are you most proud of?
If you could make one rule that everyone had to follow, what rule would you make?
What are you addicted to?
What stereotype do you completely live up to?
What is something you can never seem to finish?
As you get older, what are you becoming more and more afraid of?
What is one of your favorite smells?
What would be the scariest monster you could imagine?
What would you do if you knew you were going to die in one hour?
What book has impacted you the most?
If you had to change your name, what would you change it to?
If life is a game, like some people say, what are some of the rules?
Who is / was your most interesting friend?
What is something that your friends would consider “so you”?
What risks are worth taking?
What would be some of the most annoying things about having yourself as a roommate?
What’s something you are self-conscious about?
What personality trait do you value most and which do you dislike the most?
What’s the last adventure you went on?
When do you feel truly “alive”?
What was the most memorable gift you’ve received?
What’s something horrible that everyone should try at least once?
What were some of the turning points in your life?
What would a mirror opposite of yourself be like?
What’s the hardest lesson you’ve learned?
What mistake do you keep making again and again?
What do people think is weird about you?
If you could make a 20 second phone call to yourself at any point in your life present or future, when would you call and what would you say?
Do you feel fulfilled? What do you think would make you say yes?
What’s the best lesson your parents taught you?
What do you desire?
Have you ever had your fortune told? What did you learn?
Have you ever been hypnotized?
Do you know any magic tricks?
What holds you back?
What makes you different?
What do you do when you’re bored?
When’s the last time you broke the rules?
Describe your favorite person.
Let me see the last five interesting pictures on your camera roll.
What’s your go-to fake identity?
What’s your favorite quote?
Who would be your running mate?
What are you waiting for?
What’s the soundtrack to your life?
How do you normally meet people? Through work, friends, sports, etc?
What’s something you recently learned about yourself?
What’s the best and worse advice you’ve received and given?
What haunts you?
What are your family traditions?
What’s the best thing that’s happened to you this year?
What’s the most important thing I should know about you?
What’s your story?
What is one of your defining moments?
Who is the most important person in your life?
Tell me why your favorite person is your favorite person.
What person has had the biggest influence on you thus far?
Who do you trust the most? Who trusts you the most?
Who knows you the best?
Who do you admire?
What activity has had the biggest influence on you so far?
If you moved, what would you miss the most?
What brings you the most joy in life?
What is something you didn’t like but you are glad happened?
What small things make your day better?
What would you do after being frozen for 100 years? What would your first question be?
What’s your best find thus far?
Describe your perfect home.
What would you save from a fire?
If you died today, what would you regret leaving unsaid?
What made you last cry? Laugh out loud?
Tell me about a leap of faith you made.
What’s a seemingly inconsequential decision that changed your life the most? What’d you learn?
Who would you want as a dinner guest?
What do you wish you had known 10 years ago?
What gives your life meaning?
Fill in the blank: I wish had someone I could share _____ with.
What are your treasured memories? Reviled? Embarrassing?
What’s the most meaningful thing you’ve worked on?
Describe a perfect day.
If you could change how you were raised, would you?
What would you ask a crystal ball?
What have you dreamed of doing?
What’s your greatest accomplishment?
What & who are you grateful for?