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Top 100 Icebreaker Questions for your next meeting

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As effective as icebreaker activities can be for teams to loosen up, they are equally as important in creating a safe space for important team discussions. It is the case for Agile Retrospectives, and for any other kind of team meeting.

Whether you’re a Scrum Master, an Agile Coach, or simply a devoted contributor on your team, you know the value in getting your colleagues to open up and confront problems head on. 

Next time you lead a remote retrospective meeting, test out our list of categorized icebreaker questions to create an open and collaborative climate for more meaningful team conversations. 

In this article, you will find thoughtful questions to…

  1. Foster empathy among the team members

  2. Improve team collaboration

  3. Help team members get to better know each other

  4. Boost team morale and motivation

  5. Having difficult conversations in a healthy space

  6. Create a psychologically safe and inclusive space

  7. Laugh and relax

Icebreaker questions to foster empathy among the members

Building trust between colleagues in a virtual reality can be tough, but seeing as it’s the glue of high performing teams, we need to be intentional about it. When trust is present, people speak their minds and have the real talk needed to improve as a team. These icebreaker questions will help your team build an empathetic dynamic with one another.

1. Who is someone you admire in your life and why?

2. If you could give your younger self one piece of advice, what would it be?

3. Tell us about a time when you felt proud.

4. What are two of the most defining moments in your life?

5. What is a passion of yours outside of the office?

6. What are your greatest triggers?

7. What are you most afraid of?

8. If you were a season, which would you be and why?

9. What is something you’ve always wanted to do but haven’t yet found the courage?

10. What is something you admire about yourself?

11. Can you tell us about your dream job?

12. Tell us about the best teacher you’ve ever had.

13. Do you like your name? Why?

14. Please tell us more about the meaning of life?

15. Describe your ideal work day in one sentence.

More than 100 Icebreaker questions to break the ice and start you retrospective the right way

Icebreaker questions to improve team collaboration

Getting people with different perspectives and working styles to jive together is not always easy. These icebreaker questions focused on collaboration will help your team get on the same page.

1. What do you value most when it comes to teamwork?

2. If you could suggest three values for your team to follow, what would they be?

3. Describe your communication style in three words.

4. Why are relationships at work important?

5. What help could you use from your teammates that you haven’t asked for?

6. What impresses you most about the people on your team?

7. What do you value most in relationships at work?

8. What is something that you think your team does really well together?

9. What is your ideal collaboration style?

10. What is the best remote work tip you would like to share with your colleagues?

Icebreaker questions to help your team get to know each other as people

Knowing a little more about each member of the team is always fun. Without going too much into personal stuff, these questions will allow you to discover certain aspects of your colleagues. With great kindness.

1. Who is your favourite artist?

2. What is your all time favourite movie?

3. What was your most memorable travel experience?

4. Coffee or tea?

5. What is your favourite colour?

6. What was the last concert you went to?

7. What is your favourite TV show?

8. Where would you build your dream home?

9. If you wrote a book, what would it be about?

10. Are you an early bird or a night owl?

11. Think back. Can you remember the first CD you ever had?

12. Tell us something we don’t know about you.

13. Childhood memories! What was your favourite cereal?

14. What is your zodiac sign? Do you care about it? Why?

15. Tell us about your first job ever.

16. If you had the power to teleport yourself, where would you go right now?

17. What is your favourite videogame?

18. What is your favourite board game?

19. Who is your favourite superhero?

20. Congratulations, you just won a million dollars. What are your projects ?

Icebreaker questions to boost team morale and motivation

Teams ebb and flow when it comes to motivation and morale. When your team is in a slump, these icebreaker questions will help kick off your next meeting with a well needed boost!

1. What is a hidden talent of yours?

2. Share a moment where you surprised yourself at work.

3. What are the top three things you are most proud of about yourself?

4. What are the top three things you are most proud of about your team?

5. If you could retire right now, what would you spend your time doing?

6. If you could learn a new language, which one would you choose?

7. Would you rather give up your favourite food or give up your favourite activity?

8. What is one work-related skill that you would like to develop?

9. If you were to have one extra day off a week, what would you do with it?

10. What is the most exciting part about working virtually for you?

11. If you could travel back in time, where/when would you go and why?

12. What are you most excited about this year?

13. What was the last thing you put 100% of yourself into?

14. Who was the last person you felt inspired by?

15. Imagine you could be anywhere on Earth right now. Where would it be?

Icebreaker questions to create a safe space for difficult conversations

Before diving head first into a difficult conversation, set a collaborative, resolution-oriented tone for the meeting by asking these reflective icebreaker questions.

1. What is most important to you when it comes to communication and feedback?

2. What is one area of your own communication you would like to work on?

3. “Conflict at work is inevitable”. Explain why this is true.

4. What is the difference between confrontation and conversation?

5. What is one piece of positive feedback you can give to your coworker?

6. What do you hope to achieve from this meeting?

7. What are two things you can do to contribute to this meeting’s success?

8. Tell us about a time you felt proud of how you handled a difficult situation?

9. What is one thing you value about your team?

10. What’s the best piece of advice you’ve ever heard?

More than 100 Icebreaker questions to break the ice and start you retrospective the right way

Icebreaker questions to create a psychologically safe and inclusive space

Feelings of safety and inclusion are non-negotiables in retrospective meetings. If you want people to open up, first take the time to check in and learn how everyone is showing up to the meeting on a personal and emotional level.

1. What is something that you have learned about yourself in the past 6 months?

2. How do you recognize when you are feeling stressed at work?

3. What question do you wish people would ask you?

4. If you could describe how you are feeling today in one word, what would it be?

5. What is something you wished you learned earlier in your lifetime?

6. What would improve your day today?

7. Finish this sentence “If you really knew me, right now you’d know that….”

8. What color would best describe how you’re feeling this week and why?

9. What have you been nostalgic about recently?

10. Who has made a positive difference in your life recently? Why?

Icebreaker questions to help your team laugh and let loose

Sometimes, you need to help your team let loose and hold a retrospective meeting that reboots tired energy and gets people laughing together. It is, after all, the best medicine. 1. Who makes you laugh the most and why?

2. What is one of your pet peeves?

3. What is the most embarrassing thing you’ve ever done?

4. If an actor were to play you in a movie, who would it be and why?

5. If you could have one superpower, what would it be?

6. What is your most used emoji? Why?

7. Tonight, we're all going for karaoke. Which song will you sing?

8. If you could live in another decade, which one would you choose and why?

9. Can you tell us about your first car?

10. What is one style choice you made in the past that you wish you could take back?

11. How would you say your name if you were an alien?

12. What song have you listened to the most in your life?

13. If you were invisible for a day, what would you do?

14. When was the last time you laughed at work? What was it about?

15. Tell us about the superhero costume you would wear? Yes - you’re a superhero now.

16. Tell us about that video/meme that made you laugh recently!

17. If you were a fruit or vegetable, what would you be, and why?

18. If you could bring back any fashion trend, what would it be?

19. Would you tell us about your childhood crush?

20. Hey, Chef! What is the best dish you can cook?

There you have it! 100 questions for all different team scenarios.

We hope these will help you set the tone for your team to have the honest discussions needed to boost performance.