These ask me anything questions are sorted by who is answering: a friend, someone you just met, a teammate or a leader, a teacher or a coach, an expert or a maker. Each is short enough to type and send.
Read the full guide
Pick who is answering
Before the first card, press Topic and choose the set that fits: Ask a friend, Ask someone you just met, Ask a teammate or a leader, Ask a teacher or a coach or Ask an expert or a maker. The same panel has Easy, Medium and Hard.
Send one, or bring a few
Read the card out, or type it where the person is taking questions. For a question hour at work or a class visit, press Next card a few times and keep the three you most want answered. All 150 are listed under the deck, set by set.
Questions and answers
What are good ask me anything questions?
Ones only that person can answer, in a sentence or two: What keeps you here? Which early piece would you redo, and how? What should every new hire here know by Friday?
What are fun ask me anything questions for a friend?
Small, specific ones: What was the last thing you fixed with tape? Which object in your bag would confuse a stranger? What is the oldest thing in your fridge door?
What are the best ask me anything questions for a leader at work?
The hard ones in Ask a teammate or a leader: What are we not talking about that we should be? What would you stop doing if it were up to you alone? What have you had to unlearn as a leader?
Which questions does the list leave out?
Pay, health, bodies, romance, faith and politics, and anything about a named third person. Every question is for the one who offered to answer: about their own life, work, class or craft.
What did you do this weekend that I would not guess?
What did you eat today that you would recommend?
What did you nearly text me and then delete?
What do people thank you for most often?
What do you find hard to ask for?
What do you want to be braver about?
What do you wish I asked you about more?
What is the oldest thing in your fridge door?
What is your current screen background, and why that one?
What made you grin at your phone this week?
What should I know about you that I have never asked?
What was the last thing you fixed with tape?
What would fifteen-year-old you refuse to believe about you?
What would you keep the same if tomorrow were a do-over?
When did you last bluff your way through something?
Which decision would you make faster the second time?
Which errand have you moved to next week three times?
Which mug do you reach for first, and why that one?
Which object in your bag would confuse a stranger?
Which of your opinions about food gets the most pushback?
Which of your own rules did you break this year?
Which opinion of yours has an expiration date?
Which part of your routine would you defend to anyone?
Which photo on your phone would you frame?
Which plan of ours should we finally put a date on?
Which saying from home do you catch yourself repeating?
Which small decision turned out to matter a lot?
Which small win did you never tell anyone about?
Which song did you last play twice in a row?
Ask someone you just met 30
Are you a sunrise person or a midnight person?
What did growing up where you did teach you?
What did you want to be when you were eight?
What do you always end up explaining about your hometown?
What do you do when you get an hour to yourself?
What do you keep buying a spare of?
What do you think you are known for, and is it right?
What has taken up most of your month?
What is the best advice you got from an unlikely source?
What is the best thing you have eaten in this town?
What is your usual order at a bakery?
What made you say yes to coming?
What nearly kept you at home today?
What surprised you most about where you live now?
What was the last thing you read just for fun?
What would the eight-year-old you think of your week?
What would you study if you went back to class tomorrow?
What would your friends say you are the expert on?
Where would you be on a usual day at this hour?
Which change in your life are you still getting used to?
Which class would you sit in on for a day?
Which everyday thing do you do the slow way on purpose?
Which first impression of you is the furthest off?
Which goal of yours has a date on it?
Which lesson did you quit, and do you miss it?
Which question are you tired of answering?
Which skill did you pick up by accident?
Which smell tells you the weekend has started?
Which subject do you bring up even when nobody asked?
Which town have you lived in the shortest time?
Ask a teammate or a leader 30
What are we not talking about that we should be?
What are you working on this week?
What changed here in the last year that you are glad about?
What confused you most in your first week here?
What do you check before anything else each morning?
What do you see coming that the rest of us should prepare for?
What do you wish other teams understood about ours?
What does done mean on this team?
What does good feedback sound like to you?
What gets dropped first when your week overflows?
What have you had to unlearn as a leader?
What is the hardest call you have made in this job?
What is the team's unwritten rule?
What keeps you here?
What should every new hire here know by Friday?
What should I read in my first two weeks?
What would you like to be able to say in December?
What would you stop doing if it were up to you alone?
When did hearing the team out change your mind?
When do you ask for help, and how?
When is the worst time to interrupt you?
Where do you do your best thinking?
Which hour of your week is the busiest?
Which meeting do you never skip?
Which near miss changed how the team works?
Which process would you redesign from scratch?
Which project are you proudest of, and why?
Which shared document do you open most?
Which shortcut saves you the most time?
Which skill should I build first in this role?
Ask a teacher or a coach 30
Do you have a class tradition we should know about?
How do you like us to ask for help?
How do you want us to disagree with you?
How will we know we are improving?
What did you find hard when you were learning this?
What do you do when a lesson is not working?
What do you hope we still remember in ten years?
What do you like most about teaching this?
What do you wish every student did before walking in?
What do your best students do that anyone could copy?
What does a great class or team look like to you?
What happens when we get something wrong?
What have your students taught you?
What in this room has been here longer than you have?
What is on your desk that you would never throw away?
What is the first thing we will make or do this term?
What is the most common mistake here, and how do we dodge it?
What keeps you going on a long day?
What made you want to teach or coach?
What makes a class or a practice go well for you?
What should we call you?
What was your favorite class when you were our age?
When did you nearly quit something, and what kept you at it?
Which book would you hand to every student?
Which habit matters more than talent?
Which lesson would you still teach if nobody graded it?
Which question from a student changed how you teach?
Which rule did you once have and then drop?
Which unit or skill do you look forward to most?
Which warm-up or drill do you like best?
Ask an expert or a maker 30
How did you get started?
How do you decide what not to make?
How has your process changed since you began?
How many tries did your last piece take?
Is your workspace silent or noisy?
What are you making right now?
What are you still trying to figure out?
What did you give up to get good at this?
What did you once believe about your craft that turned out wrong?
What do beginners buy that they do not need?
What do people get wrong about your field?
What do you do when you are stuck?
What does success mean to you now, compared with when you started?
What does the first hour of a project look like?
What does your workspace smell like?
What is always on your worktable?
What is the smallest thing you have made that you love?
What is underrated in your field?
What should a beginner practice every day?
What will beginners in your field learn first, twenty years on?
What would you make if nobody ever saw it?
What would you tell someone ten years behind you?
When do you put the tools down for the day?
Where do your ideas usually start?
Which early piece would you redo, and how?
Which mistake taught you the most?
Which part of the work do you still find hard?
Which piece of criticism changed your work?
Which problem in your field is nobody close to solving?
Which tool do you reach for most?
How this list was compiled
Written by the Game Night Generator editors on 2 October 2026; every question is our own wording and no list was copied from anywhere. 150 questions to put to one person who has said "ask me anything", 30 in each of five sets sorted by who is answering: a friend, someone you have just met, a teammate or a leader at work, a teacher or a coach, and an expert or a maker. Each is short enough to type and send. Easy questions take a word or a sentence, medium ones a short story, hard ones some thought. Nothing asks about pay, health, a body, a romance, faith or politics, none asks about a named person other than the one answering, and none asks for an account-security answer (a pet's name, a school, a street, a first job or car). Licence: own work