For
Questions for your coworker
9 hand-curated question banks for the topics most worth covering with your coworker. About 30 questions per set, ordered from warm-up to vulnerable.
A few questions from these sets
- Life lessons What did learning to set a boundary at work teach you?
- The future What is our industry going to be embarrassed about in ten years?
- Values Have you ever actually refused to do something here — not would you, did you?
- Work and career What almost became your career instead?
- Deep questions What does a good life look like to you, outside of any job?
- Fun & icebreakers Would you rather every meeting came with an agenda, or every meeting came with notes afterwards?
- Hypotheticals If you could have any other job in this company for a week, whose chair do you steal?
- To get to know deeper Where did you grow up — and what do people always get wrong about the place?
- To reconnect Do you feel like work has changed much since we used to work closely?
- Life lessons
30 Questions to Ask a Coworker About Life Lessons
30 questions to ask a coworker about the lessons they've learned — thoughtful, professionally appropriate, and a real way to know the person beside the role.
- The future
50 Questions to Ask a Coworker About the Future — the Work's, Not the CV's
50 questions to ask a coworker about the future: where the work is heading, what this team is becoming, and what you are each building toward.
- Values
50 Questions to Ask a Coworker About Values — the Ones That Are Safe to Ask
50 values questions you can actually ask a coworker: what they refuse to cut, who the work is for, and where the line runs between person and role.
- Work and career
32 Questions to Ask a Coworker About Their Work and Career
32 career-story questions colleagues never ask each other — how they got here, the job that taught them most, what they'd tell their younger self.
- Deep questions
30 Deep Questions to Ask a Coworker You Trust
30 deep questions for a coworker you want a real connection with — past the small talk, without crossing the lines a workplace friendship still respects.
- Fun & icebreakers
50 Fun Questions to Ask Coworkers — Icebreakers Nobody Has to Perform For
50 fun, low-stakes questions for coworkers — icebreakers for standups, retros, and team lunches that nobody has to perform for.
- Hypotheticals
50 Hypothetical Questions to Ask a Coworker
50 light, workplace-safe hypothetical questions for a coworker — what-ifs that break the ice without crossing a single professional line.
- To get to know deeper
30 Questions to Get to Know a Coworker Beyond the Job Title
30 workplace-safe questions to turn a colleague into a real work friendship — warm, boundaried, and ordered from small talk to actual talk.
- To reconnect
30 Questions to Reconnect With a Coworker
30 questions to reconnect with a coworker — after a team change, a long stretch heads-down, or a friendship that quietly went quiet. Warm, not awkward.