- What's the most frustrating part about your job? Your day?
- What do you hear your colleagues complain about the most?
- What's one part of your job you wish you didn't have to do?
- Are there any daily tasks you would like to outsource?
- How have you tried to simplify or reduce your workload?
- What's one problem you've been trying to solve over time?
- (Seriously), what keeps you up at night?
- Is there anything you'd like to fix that your boss won't go for?
- If you had unlimited resources, how would you simplify your job?
- What is the least favorite part about your career?
- What advice (that you didn't get) would you give about your job?
- What took the longest to learn on your own? Why?
- If you had a magic wand for work, what would you wave it on?
- How would you scare me out of "wanting" your career?
- What's one thought about your job you wouldn't tell your boss?
- Tell me about the most painful customer experience you've had.
- If you were given $5,000 to spend on your job, where would you use it?
- When do you find yourself hesitating the most?
- What's your biggest professional fear?
- What do you think your boss's or customer's biggest fear is?
- Have you ever thought about spinning off? What would you do?
- Oh, Really? Why's That? (Don't forget to ALWAYS dig deeper).
- When is the last time you missed a deadline, why?
- What would you hire a consultant to help you with?
- What makes you the most nervous about your job?
- Who do you think your biggest competition is? Why?
- If you didn’t have to sleep, what would you do with the extra time?
- What's your favorite piece of clothing you own/owned?
- What hobby would you get into if time and money weren’t an issue?
- What would your perfect room look like?
- What fictional place would you most like to go to?
- What job would you be terrible at?
- When was the last time you climbed a tree?
- What is the most annoying habit that other people have?
- What skill would you like most to master?
- What would be the most amazing adventure to go on?
- What state or country do you never want to go back to?
- What songs have you completely memorized?
- What game or movie universe would you most like to live in?
- What do you consider to be your best find?
- Are you usually early or late?
- What pets did you have while growing up?
- When people come to you for help, what do they usually want help with?
- What takes up too much of your time?
- What do you wish you knew more about?
- What’s the best way to start the day?
- Who has impressed you most with what they’ve accomplished?
- What’s your claim to fame?
- What’s something you like to do the old-fashioned way?
- What’s your favorite book or movie? Why?
- How often do you people watch?
- What have you only recently formed an opinion about?
- What’s the best single day on the calendar?
- What are you interested in that most people haven’t heard of?
- What’s the farthest you’ve ever been from home?
- What is the most heartwarming thing you’ve ever seen?
- What could you give a 40-minute presentation on with absolutely no preparation?
- What is something you think everybody should do at least once in their lives?
- What’s your dream car?
- What’s worth spending more on to get the best?
- What are you most looking forward to in the next 10 years?
- Where’s the most interesting place you’ve been?
- What’s something you’ve been meaning to try but just haven’t gotten around to it?
- What’s the best thing that happened to you last week?
- What do you wish you could erase from your mind so that you could experience it for the first time again?
- If all jobs had the same pay and hours, what job would you like to have?
- How different was your life one year ago?
- What do you hope never changes?
- Why did you divide to do the work you are doing now?
- What’s the best way a person can spend their time?
- What is the luckiest thing that has happened to you?
- What are some things you’ve had to unlearn?
- What are you looking forward to in the coming months?
- What website do you visit most often?
- What one thing do you really want but can’t afford?
- Where do you usually go when you have time off?
- What is special about the place you grew up?
- What are you most likely to become famous for?
- What are you absolutely determined to do?
- What is the most impressive thing you know how to do?
- 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 do you think you would grow out of but haven’t?
- In what situation would you feel the most out of place in?
- What’s the dumbest thing you’ve done that actually turned out pretty well?
- If you had to write a book, what would it 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?
- What is the strangest thing you have come across?
- What is something you are certain you’ll never experience?
- What are you addicted 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 song or artist do you like, but rarely admit to liking?
- What would you do if you knew you were going to die in one hour?
- What book impacted you the most?
- If life is a game like some people say, what are some of the rules?
- Who is your most interesting friend?
- What is something that your friends would consider “so you”?
- What risks are worth taking?
- What can you not get right, no matter how many times you try?
- What do you take for granted?
- What’s something you are self-conscious about?
- What irrational fear do you have?
- What’s the best advice you’ve ever received?
- What makes a good life?
- What’s the last adventure you went on?
- When do you feel truly “alive”?
- What was the most memorable gift you’ve ever received?
- What chapters would you separate your autobiography into?
- What statistic for your life would you most like to see?
- What’s something horrible that everyone should try at least once?
- Have you ever saved someone’s life?
- What were some of the turning points in your life?
- What would a mirror opposite of yourself be like?
- What are you really good at, but kind of embarrassed that you’re good at it?
- Which of your scars has the best story behind it?
- What’s the title of the current chapter of your life?
- What’s the hardest lesson you’ve learned?
- What mistake do you keep making again and again?
- What have you created that you are most proud of?
- If you could make a 20-second phone call to yourself at any point in your life, when would you call and what would you say?
- What do you have doubts about?
- What bends your mind every time you think about it?
- What’s the best thing you got from your parents?
- What is the “holy grail” of your life?
- In your group of friends, what role do you play?
- What’s the most immature thing that you do?
- What's the best and worst thing about getting older?
- What’s something that happened or something that someone said that changed how you view the world?
- What are you most likely very wrong about?
- What lifestyle change have you been meaning to make for a while now?
- If you could have a video of any one event in your life, what would you choose?
- What’s the most illegal thing you’ve done?
- What is the biggest lesson you never learned?
- How do you hope you’ll change as a person in the future?
- What lie do you tell yourself most often?
- How do you choose to suffer?
- What do you regret not doing?
- What gives your life meaning?
- What do you most often look down on people for?
- What bridges do you not regret burning?
- What are you most insecure about?
- How do you get in the way of your own success?
- What’s the one thing you did, that you really wish you could go back and undo?
Reminds me of the 36 questions to fall in love experiment
https://www.mindbodygreen.com/articles/36-questions-to-fall-in-love
I thought it will be link dumping but its good
Yeah. Probably because the title sounds super click-baity. Changed it to something less click-baity. List better be good. I've beeb collecting these over years 😅