CCulture Experts

Library

Questions that surface real culture.

A working library of prompts for workshops, retrospectives, one-on-ones, and employee listening — designed to get past the polished answer.

Workshops

  • If our culture had a tagline that was honest, what would it say?
  • Which of our stated values would a new hire experience in their first week?
  • What behavior do we tolerate that quietly contradicts our values?
  • If we could only keep three values, which would we keep — and why?

Retrospectives

  • What did we do this quarter that felt most like us at our best?
  • Where did our process get in the way of our values?
  • What's one ritual we should start, stop, or change?
  • Who deserves credit that hasn't been said out loud yet?

1:1s

  • What's one thing about how we work that frustrates you?
  • When did you feel most proud of your work recently?
  • What do you need more of from me as your manager?
  • What's something you've been thinking about saying but haven't?

Employee listening

  • Do you feel safe to disagree with your manager? Why or why not?
  • If a friend asked what it's really like to work here, what would you say?
  • Where do our stated values show up most? Least?
  • What's one thing leadership could do this month that would meaningfully change your week?

Onboarding & first 90 days

  • What surprised you most in your first two weeks — good or bad?
  • What did you have to figure out on your own that should have been told to you?
  • Who explained 'how things really work here' to you, and what did they say?
  • What did you expect from us in the interview process that hasn't shown up yet?

Exit interviews

  • When did you first start thinking about leaving?
  • What would have had to change for you to stay?
  • What did you stop bringing up because it never went anywhere?
  • What should we ask the next person in this role that we didn't ask you?

Leadership & board

  • What are we pretending not to know?
  • Which decision this quarter would we make differently if our values were the tiebreaker?
  • Who on this team would tell us we're wrong, and when did they last do it?
  • What behavior are we rewarding that we say we don't want?

Trust & psychological safety

  • What's the last mistake that was talked about openly here — and what happened to the person?
  • Where do people go quiet in meetings, and what's the topic?
  • If you saw something unethical, who would you tell — and would anything happen?
  • What question feels risky to ask out loud on this team?

Hybrid & remote

  • What information only travels in the room and never reaches people who aren't there?
  • Which meeting could be a document, and which document should be a conversation?
  • How do you know you're doing well when nobody sees you work?
  • What's the cost of being the remote person on this team?

Performance & growth

  • What feedback have you received that actually changed how you work?
  • What are you great at that this role never asks you to use?
  • What would the next step in your career here look like — and does it exist?
  • Who here has a career you'd want, and what did they do to get it?

Change & crisis

  • What are people saying about this change when leaders aren't in the room?
  • What did we promise during the last change that we didn't deliver?
  • What should stay exactly the same, no matter what else changes?
  • Who is carrying the most invisible work through this transition?

Belonging & inclusion

  • Whose ideas get repeated and credited here — and whose don't?
  • What do you have to hide or soften to fit in at work?
  • Where does our hiring bar measure sameness instead of ability?
  • Who gets the benefit of the doubt here, and who has to earn it twice?

Customer & quality

  • When did we last choose speed over the standard we claim to hold?
  • What do customers say about us that we've stopped listening to?
  • Who is allowed to stop the line when something isn't right?
  • What problem do we keep fixing instead of solving?

Meetings & decisions

  • Who actually decided the last big thing, and how did you find out?
  • Which recurring meeting would nobody miss if it disappeared?
  • Where do decisions go to die here?
  • What gets agreed in the room and undone in the hallway?