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25 questions

Deep icebreaker questions

Once a team knows each other's names, hobbies and coffee orders, small talk stops building anything new. Thoughtful questions about values, lessons and what people care about help a team understand why colleagues work the way they do.

These questions go deeper without going personal in a way that belongs outside work. Nothing asks about health, relationships, money troubles or beliefs, and every question can be answered at whatever depth the person chooses.

What is something you believed strongly five years ago that you see differently now?

All 25 questions

  1. What is something you believed strongly five years ago that you see differently now?
  2. Who has had the biggest influence on how you work, and what did they teach you?
  3. What is a moment you were proud of that nobody else noticed?
  4. What does a meaningful day look like to you?
  5. What is a lesson you learned the hard way?
  6. What is something you are still learning about yourself?
  7. What would you spend your time on if you had a whole year free?
  8. Which values do you try to bring to every team you join?
  9. What is a piece of advice you would give your younger self?
  10. What is a challenge you are glad you went through?
  11. What is a small kindness someone showed you that you still remember?
  12. When do you feel most like yourself?
  13. What would you like to be remembered for at work?
  14. What is a skill that took you a long time to learn but was worth it?
  15. What does trust in a team look like to you?
  16. What is a question you wish people asked you more often?
  17. Which book or idea changed the way you see the world?
  18. What are you curious about at the moment?
  19. When was the last time you changed your mind about something important?
  20. What is one thing that gives you energy when work gets hard?
  21. What does success mean to you right now?
  22. What is a tradition from your family or culture that you value?
  23. Who is someone you would like to thank but never have?
  24. What are you looking forward to in the next year?
  25. What is one thing you want to get better at as a teammate?

Tips for using these questions

  • Use these with groups that already trust each other, and always make passing an easy option.
  • Give people a minute to think before anyone answers.
  • Answer first yourself, and set the depth by example: honest, but not more than you would want others to share.

Need a speaking order or groups? The team generator and turn picker makes them in one click. For more ideas, read how to run an icebreaker that people actually enjoy.

Questions people ask

How many deeper questions questions should I use in one session?

One question is enough for a regular meeting. For a workshop or a team's first session, two or three work well. Save the rest for later meetings so they stay fresh.

What if someone does not want to answer?

Let them pass, without comment. A forced answer makes the whole group less comfortable, and the point of an icebreaker is the opposite.

Can I print this list?

Yes. Print the page from your browser, or copy the questions into your own slides or notes.

More icebreaker questions