84 fun questions to ask coworkers, for every situation
Pick the moment you're in, then bring three questions. Every one is safe to ask at work.
These 84 fun questions to ask coworkers are for one-on-one talk: a new hire’s first week, a coffee chat, a video call with a remote teammate, lunch, or someone from another team. Each list fits its moment, and the last ones go deeper for coworkers you already know. Then come 12 funny questions with sample answers and a short list of questions to skip.
Questions to ask a new coworker
Their first weeks. Keep it easy to answer and show you're glad they're here.
- What did you do before this job that still comes in handy?
- What has this place done well in your first weeks?
- Which part of the job are you most curious to try?
- How do you like to get questions: chat, email or a quick hello at your desk?
- Are you sharper in the morning or the afternoon?
- How does the commute compare with your last job?
- Have you found a decent lunch spot near here yet?
- Which habit from your last job are you keeping?
- Which part of how we do things here still feels unclear?
- What did your last workplace get right that we should borrow?
- What do you like to do on a Saturday with nothing planned?
- Who else have you met so far, and who should I introduce you to?
Coffee chat questions
Fifteen to thirty minutes, one-on-one. Three or four of these fill it nicely.
- How do you take your coffee, and how strict are you about it?
- What's on your calendar this month that you can't wait for?
- What has been taking up most of your brain lately?
- What did you finish recently that you're quietly proud of?
- What small thing made your week better?
- What are you teaching yourself at the moment?
- Which boss taught you the most, and how?
- Which part of your workday do you guard from meetings?
- What podcast, show or book should I add to my list?
- What do people outside your team usually get wrong about your job?
- Which other team's work would you like to shadow for a day?
- What's a place you used to live that you still miss?
Questions to ask a remote coworker on video
You can't bump into each other in the kitchen, so ask about their world on the other side of the camera.
- What's on your desk that I can't see on camera?
- What can you see when you look up from your screen?
- What time does the sun go down where you are this week?
- Who keeps you company during the day: pets, people or plants?
- What's the best part of working from home, and the hardest?
- How do you mark the end of your workday?
- What local food does everyone near you swear by?
- What's the best thing you've added to your workspace this year?
- What do you like most about the town you work from?
- What do you do on your lunch break when nobody's watching?
- If I visited your town, where should we go for coffee?
- What's one thing about working with our team that's easier in person?
Fun questions to ask coworkers at lunch
Food is the easiest subject at the table. Start there and see where it goes.
- What's the best lunch you've had near the office?
- Do you pack lunch the night before or decide at noon?
- What do you cook when you want to impress someone?
- What food from growing up do you still crave?
- What's the oddest thing you've spotted on a menu?
- What's your usual order at a place you love?
- If one restaurant could open next door to the office, which should it be?
- What have you been meaning to try cooking?
- Which dish do you order to judge a new restaurant?
- Which snack would you defend to the end?
- Is there a recipe people ask you to bring?
- What meal would you get on a plane for?
Questions to ask a coworker on another team
Good for cross-team coffee, a new project or a mentor match. Curious beats clever here.
- What does your team actually spend most of its day on?
- Which month is the wildest on your team's calendar?
- Which request lands on your team more than any other?
- What makes a request to your team easy to say yes to?
- How does your team know it had a great quarter?
- Which tools does your team live in all day?
- What did your team ship lately that more people should know about?
- How did you end up on that team?
- Which teammate of yours should I grab coffee with?
- Which word or acronym does your team use that confuses everyone else?
- Where does your work cross paths with what my team does?
- Which part of your team's work deserves more credit?
Meeting a lot of people at once? These speed networking questions are built for three-minute rounds.
Deeper questions for a coworker you already know
Thought-provoking ones for a long lunch or a walk. Offer your own answer first.
- What have you changed your mind about in the last few years?
- Which task at work feels more like a hobby?
- What's the bravest career move you've made?
- What are you proud of that never made it onto a resume?
- What's a skill you picked up here that you never expected to need?
- What would you do with a paid month off?
- What skill would you like to be known for in five years?
- What lesson did you learn the hard way at work?
- What do people often misread about you at first?
- What matters most to you outside these walls?
- Which tradition would you like to start or keep going?
- What's something hard you'd happily do again?
Funny questions to ask coworkers, with answers
Each comes with an answer of ours, so you can go first and set the tone.
- What's the most useless thing you're weirdly good at?Guessing the exact time without a clock.
- What's the strangest item in your junk drawer?A single key that opens nothing I own.
- What would your phone's autocorrect say about you?That I type “on my way” a lot more than I leave.
- Which everyday sound can you not stand?A spoon scraping the bottom of a yogurt cup.
- Which word do you misspell every single time?Necessary. One c or two? Every time.
- Which chore would you pay almost anything to never do again?Untangling the cords behind the TV.
- What were you oddly afraid of as a kid?The drain in the bathtub.
- What would your pet say your job is?Staring at a glowing rectangle instead of throwing the ball.
- What would the TV show about your week be called?“You're on Mute: Season Four.”
- What's a tiny opinion you'll defend forever?Ice cubes from a tray beat the ones from the machine.
- What's the most dramatic thing you've done to dodge a phone call?Let it ring out, then texted “what's up?” ten seconds later.
- Where's the oddest place you've found your keys?In the fridge, next to the butter.
What not to ask a coworker
Six questions that put people on the spot, and what to ask instead.
Skip: “How much do you make?” Pay puts people on the spot.
Ask: “What's been the best surprise about working here?”
Skip: “Are you looking for another job?” There's no safe answer.
Ask: “Which part of your job would you happily do all day?”
Skip: “What do you really think of our manager?” It invites gossip they can't take back.
Ask: “Whose work here do you look up to?”
Skip: “When are you having kids?” Family plans are private.
Ask: “What's filling your weekends lately?”
Skip: “Have you lost weight?” Comments on bodies land badly, even as praise.
Ask: “What's something you've been enjoying lately?”
Skip: “Who did you vote for?” Politics can split a team for good.
Ask: “What's the best thing you read this week?”
Meet more coworkers at once
One-on-one questions take time. A hosted hour gets a whole team talking, in person or on video.
Three hosted events for getting to know people, with today’s prices.
Speed Networking pairs people in private video rooms for three-minute one-on-one chats, so everyone meets a string of new coworkers in 45 minutes. A coffee tasting ships a kit to everyone for a hosted tasting on video (book about 3 weeks ahead), and a virtual game show mixes people into small teams. See all virtual networking and coffee tasting options, or get a free quote. For a group setting, try these team building questions, start meetings with check-in questions, or settle something silly with debate games.
