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Retrospective resources

144 Icebreaker Questions to Kick Off Retrospectives

A quiet group that needs a nudge, or a good retro that deserves a laugh first: pick one question, go around the room, then open the board. Grouped by mood so you can find the right one in seconds.

The first few minutes of a meeting decide who talks for the rest of it. Someone who has already answered one easy question keeps contributing when the retrospective gets to the hard part. That is the whole job of an icebreaker: every voice heard once, in under three minutes, before the real discussion.

Use one per retro and rotate through the groups. Pair it with a format from the retrospective formats library, and run the board itself on ScatterSpoke retro boards, free.

Quick check-ins

One-word or one-number answers. Thirty seconds around the room and everyone has spoken once.

  1. Which animal best represents you today?
  2. If your mood today was an emoji, which emoji would it be?
  3. On the scale of 1 (low) - 5 (high), what is your level of morale like today?
  4. On the scale from 1 (not too busy) to 10 (too busy for my own good), how busy are you this week?
  5. If your mood were a season, which season would you be today?
  6. If your mood today was a musical genre, which one would it be?
  7. What is the theme song of your day?
  8. If this year were a song, which song would it be?
  9. Which movie soundtrack is the soundtrack to your life?
  10. What calms your nerves?
  11. Name one thing that stresses you out without fail.
  12. Are you a morning person or a night owl?
  13. How dependent on caffeine are you in order to start your day off right?
  14. When you wake up in the morning, what’s the first thing you read?
  15. What’s your favorite day of the week? Why?
  16. What’s the first tab you have open in your browser right now?
  17. What’s your desktop background?
  18. What’s your cellphone wallpaper right now?

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This or that

Two choices, no wrong answer. Good for a group that still needs a nudge to talk.

  1. Would you rather sit through a Star Wars marathon or a Lord of the Rings marathon?
  2. If you could choose one, what would it be: working in an office or working from home?
  3. Would you rather see Prince or Freddie Mercury in concert?
  4. If you had to go without drinking coffee or tea for the rest of your life, which one would you choose to live without?
  5. Do you prefer Slack or Zoom for work-related conversations?
  6. Are you a cat person or a dog person?
  7. Would you rather travel to Italy for a week or do a stay-cation in your own town?
  8. Would you rather post on TikTok or Instagram?
  9. If you could go back in time, which decade would you travel to?
  10. If you could stay an age all your life, what age would you choose?
  11. If you weren't born in the country in which you were, where would you want to be from?
  12. If you won a trip for two to Las Vegas, who would you take with you?
  13. Which famous actor/actress would play you in the movie about your life?
  14. Which fictional workplace do you imagine yourself fitting in?
  15. Which TV show most resembles your life right now?

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Funny and lighthearted

For the retro that needs a laugh before it needs a plan.

  1. How would you caption this GIF? (share GIF in chat)
  2. What is the weirdest thing in your Netflix queue right now?
  3. What is your go-to karaoke song?
  4. If you had to get a silly tattoo on a dare, what would it be?
  5. What’s your favorite dad joke?
  6. What is your go-to dance move?
  7. What’s the last thing that embarrassed you?
  8. Name something funny your pet does when they’re at home.
  9. If you were Batman, which member of the team would be Robin?
  10. If you could sing a duet with anyone on this team, who would you sing with?
  11. Which celebrity would you be able to survive a duo road trip with?
  12. Which fictional character would you most like to have dinner with?
  13. If you could have any superpower, what would it be?
  14. If you had $1M, but couldn’t spend a penny of it on yourself, what would you spend it on?
  15. If you didn’t have to sleep, how would you spend these extra 8 hours?
  16. If you could have unlimited supply to one thing for the rest of your life, what is it?
  17. If it were your birthday today, what gift would you like to receive?
  18. If you had to cook a meal with your team, which meal would you cook?
  19. What country would you visit with your team for a week?
  20. If your team at work was a sports team, what sport would you play?
  21. If you had met your team for the first time outside of the work context, where would you have met?

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Getting to know each other

Stories and preferences. Best for new groups and for the sprint after a reorg.

  1. What was your least favorite class in high school?
  2. What was your first job ever?
  3. How would you describe your personality when you were a kid vs your personality now, in one word?
  4. What is the last place, outside of the country in which you live, that you travelled?
  5. What did you want to be when you grew up?
  6. If you played a musical instrument, which would you play?
  7. If you weren’t in your current role, what job would you be doing?
  8. What’s one food you couldn’t live without?
  9. What’s your favorite way to commute? (ex. car, public transport, bike or walking)
  10. Share something no one on the call would guess about you.
  11. What’s your current obsession?
  12. What’s one dream you recently had?
  13. Share one crazy thing you’ve done recently. Why was it crazy?
  14. What’s your favorite healthy food?
  15. What’s your favorite guilty pleasure?
  16. What’s your ideal road trip?
  17. What does a great vacation look like to you?
  18. What’s the last TV show you binge watched?
  19. Share two truths and a lie with the group.
  20. Name one thing that’s really changed about your hometown in the last 10 years.
  21. If you could make one of your childhood dreams come true, which one would you choose?
  22. What’s something you’ve really missed doing, but never have time?
  23. What’s one documentary you recently watched and loved?
  24. What’s the story of your name?
  25. Are you named after anyone?
  26. If you could go back to college, what would you major in?
  27. Name something you think is cool that most people think is boring.
  28. What’s something that you will never understand?
  29. What’s your best purchase this past year?
  30. What is the last book you read?
  31. What song do you jam to while you work?
  32. If you had to live by one quote, what would it be?

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Work and remote life

About the job and the desk. These often surface a real improvement before the retro even starts.

  1. Share something new in your work space with the group.
  2. Name three things that are always on your desk in your home office space.
  3. What’s one manual thing that you wish could be automated in your job?
  4. Name one tool that will help you do your job better.
  5. What’s your pet peeve at work?
  6. What’s your pet peeve at home?
  7. What’s the best part about working from home?
  8. What’s the worst part about working from home?
  9. What does an awesome day at work look like?
  10. How do you spend your lunch break?
  11. Name something you do regularly, but should really delegate down the line.
  12. What’s something you didn’t know about the company you work at on your first day?
  13. Where does your to-do list live?
  14. How do you decide what you will focus on in a given day?
  15. What’s the first thing that pops into your head when I say the word: teamwork?
  16. What’s the most difficult job in the world?
  17. If you could trade roles with anyone on your team, who would it be?

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Wins, lessons and growth

Reflective questions that set the tone for a retrospective: what went well, what was hard, what changed.

  1. If we’re celebrating something that happened to you this month, what are we celebrating?
  2. Which professional skill do you hope to develop in your lifetime?
  3. Which personal skill do you hope to develop in your lifetime?
  4. What have you learned about yourself during the pandemic?
  5. Tell us about the task you did at work that truly challenged you and why.
  6. Share a challenge that you have overcome in the past year.
  7. Name one thing you absolutely rock at.
  8. Name one thing you absolutely suck at.
  9. What is one thing you appreciate knowing today?
  10. What is one thing you wish you had learned sooner in life?
  11. What is the last thing that shocked you?
  12. Share your latest revelation with the team.
  13. What’s the last thing you did at work that made you feel proud of yourself?
  14. What’s the last thing you did at home that made you feel proud of yourself?
  15. Share a game-changing life hack that you recently discovered.
  16. What’s one of the biggest risks you’ve taken in your life or career that really paid off?
  17. Share something you discovered at work that surprised you.
  18. Tell us about the last event you went to that blew your mind.
  19. Name someone in your life that inspires you?
  20. Name a historical figure that inspires you?
  21. How do you keep yourself motivated?
  22. What’s something you most need help with in your life right now?
  23. Have you tried something for the first time recently?
  24. What’s the most difficult thing you’ve had to learn how to do recently?
  25. What’s the best piece of advice you have ever received?
  26. What is the wisest thing someone has told you lately?
  27. What’s one thing you’ve been putting off for a long time?
  28. What bad habit have you kicked and how did you do it?
  29. What good habit have you cultivated recently?
  30. What’s one area in which you could use a mentor to improve?
  31. If you had to step in to teach a high school class today, which subject would you teach?

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For team meetings

For a weekly meeting or a kickoff rather than a retro: quick to answer, and each one tells the group something useful about the week ahead.

  1. What’s one thing you’re looking forward to this week?
  2. What’s the most useful thing you learned since we last met?
  3. What’s one small win from last week nobody heard about?
  4. What’s on your plate this week that the rest of us might not know about?
  5. If you could clear one meeting from your calendar this week, which would it be?
  6. What’s one tool or shortcut that saved you time recently?
  7. Who helped you out lately, and how?
  8. What’s one word for how this week is going so far?
  9. What’s something you’re stuck on that someone here might help with?
  10. What would make this meeting worth your time today?

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How to use them

How do you use an icebreaker in a retrospective?
Pick one question, give everyone thirty seconds to answer in turn, then open the retro. Two or three minutes in total. The point is that every voice has been heard once before the real discussion starts.
Why start a retrospective with an icebreaker?
People who speak early in a meeting keep speaking. A quiet group that has already answered one easy question is far more likely to add ideas and action items when the retro gets to the hard part.
How many icebreaker questions do you need?
One per retro. Rotate through a different group each sprint so nobody gets the same question twice, and keep the reflective ones for retros where the tone matters.
Which icebreakers work best for remote retrospectives?
The quick check-ins and the this-or-that questions: they need no props, can be answered in chat, and take seconds. Save the story questions for a group that already knows each other.
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