How to play 21 Questions

Here's a fun game to play the next time you're in a group setting and want to get everyone involved somehow. Simply go around in a circle and take turns answering questions from the list. If somebody doesn't like the question, they can skip to the next one. The aim of the game is to get everybody participating and comfortable with one another.

Icebreaker Games for Remote Meetings

If you're looking for more ways to break the ice in your remote meetings, be sure to check out Brightful Meeting Games. We've put together the best list of questions, trivia, games for you to play, all for free!

Here is our list of questions for the 21 Questions game

1. What is the TLDR version of your life?

This question will help you understand what they think is important. If their answer gets included in the highlight reel of their life so far, it must be pretty important to how they see themselves and their place in the world.

2. What is something that you have always wanted to try but never have?

You might be surprised what some of your peers and friends would like to try. It's an opportunity to try something new with them or maybe it's an opportunity to introduce them to a new idea.

3. What is your favorite place in the world and why?

If your peer loves to travel, this is a question they are bound to have an interesting story or two about.

4. What do you do for fun?

You might be surprised with the answer to this one. People find interesting ways to have fun.

5. What is your favorite TV show, movie, or book?

This is a great question to try to get your peer to explain why they liked something. In the explanation, they are bound to have a story to tell.

6. What is one question you would ask the founder of X if you could?

I love asking this question of people that work at small tech startups. What's their go-to question for the founder?

7. What do you value more than anything else?

Your peer should answer this in a way that gives you an understanding of what they value and why they value it. This is where you'll learn their priorities.

8. What is your idea of a good time?

The idea of a good time will depend on who you ask. This question is interesting for the answer and also for the differences between what they think is a good time versus what you might think is a good time.

9. If you could live anywhere in the world, where would you live?

This can lead to a discussion about favorite cities, favorite countries, travel stories, etc.

10. What is your favorite sports team?

Maybe you both like the same team, maybe not. Either way, there will be a story or two about why your peer likes their team.

11. What do you like most about X?

This is a great question for the first few months at a job or internship. It helps the new person get to know their peers and also learn more about the organization they're joining.

12. If you could tell your younger self one thing, what would it be?

What would your peer's younger self have to change? I've been told that you need to do things and see things in order to learn and better yourself. This question should make the other person think about what they could've done better in their life.

13. What would you put on your own personal billboard?

What would your peer like to be famous for? What would they like people to read on their own billboard?

14. What do you spend too much time thinking about?

Have you ever heard a song you didn't like, but the tune wouldn't leave your head? You were thinking about it all the time even though you didn't like it. This question is like that for people. I'm curious what your peer has been thinking about a lot lately.

15. What is one possession you can't live without?

Maybe you have an opinion about what a person's answer will be to this question. Do you think a person will say their phone, or maybe a photo of a loved one? I think it's something deeper than that, something that makes them who they are. What do they need to keep them grounded and connected to their life's purpose?

16. If you had unlimited money or time, what would you do?

What would they be doing with their life if they had unlimited money? Time?

17. What is your favorite thing about working at/with X?

The answer to this question will reveal the key aspects of your peers' workplace. This is an opportunity to learn more about your organization from an insider's perspective.

18. What do you do when you are feeling really down?

What helps your peer feel better when they are down? Maybe they listen to a certain song, or take a trip to a certain place, or hang out with a certain group of people. I'm curious to know what your peer does to turn things around.

19. What is your favorite photo that you took?

Maybe your peer is a talented photographer. I'm curious what they find most meaningful or intriguing about their photo. I'm sure there's a story attached.

20. What is one thing you have always wanted to accomplish?

This is an open-ended question, similar to the last one. People have big dreams and hopefully they're working on one or two of them. Maybe they've made progress on them already. I'm curious what your peer has always wanted to accomplish.

21. What is the most important thing you have learned?

I like to think about this as an opportunity for my peer to reflect on their life. There is a chance they may say something that's important to their life right now, or they might talk about something that they learned a long time ago but is still meaningful.

This list was hard to make. I asked a lot of questions to find the best ones. What would you add or take away? Leave a comment!