120 Interesting What If Questions to Make Your Team Think Outside the Box

Planning a team-building event and want to ramp up the fun? “What If” and “What Would You Do If” are perfect icebreaker questions to kickstart creative conversations at your next team party. Whether it’s choosing between a million bucks or the power to fly, or imagining yourself as CEO for a day, these questions are sure to get everyone thinking outside the box and bonding in no time. 

To make things easier, we have compiled a list of 120 What If questions across different categories that are guaranteed to be crowd-pleasers.

Table of Content 

What are What If Questions?

What If questions are hypothetical scenarios where team members take turns sharing their answers to the given statement. These questions can be like, ‘’What if you could swap lives with your role model?’’ This game challenges creativity, strengthens critical thinking, and works as an amazing icebreaker activity as well. You can ask questions from categories like pop culture, food, sports, and more.  It can also be included in your list of virtual team building activities  if your team works remotely.

120 What If Questions to Ask Your Co-Workers

What if questions are the best way to break those awkward pauses during team gatherings and help your team know each other better. Below is a list of 120 fun questions to ask your co-workers for a good laugh and shared memories. 

What If Questions for Work

Hectic schedules can lead to fewer conversations with your colleagues outside daily standups. These What If questions will help you and your team to explore each other’s take on these imaginary work situations. 

1. What if your laptop stopped working for a day?
2. What if you could take a sabbatical to pursue your passion project?
3. What if you become the boss for a day?
4. What if you could choose your working hours?
5. What if you are in charge of planning holiday parties?
6. What if you could implement a four-day workweek?
7. What if you could swap tasks for a day?
8. What if you could introduce a random holiday?
9. What if you could redesign your office space?
10. What if you had unlimited vacation days?
11. What if you could invite your favorite celebrity to an office event?
12. What if you could offer a new perk to your team?
13. What if you could add your favorite activity to team-building sessions?
14. What if you could make a work playlist for your team?
15. What if you had a ‘’no technology’’ hour at work?
16. What if you could choose an industry leader as your mentor?
17. What if you had to perform for a company-wide talent show?
18. What if you could plan an entire team retreat?
19. What if you could bring pets to work?
20. What if you could introduce social clubs in the office?
21. What if you had a 30-minute nap time after lunch break?
22. What if you had to communicate with your team through songs for a week?
23. What if you could have a personal assistant for a month?
24. What if you don’t have to attend any meetings for a week?

What If questions on Pop culture

From acting on a TV show to writing a script, discover your teams’ thoughts on some fictional prompts. This pop culture what if questions cover every possible scenario in movies, music, and TV shows to bond over some fun banter. 

1. What if classic sitcoms had modern reboots?
2. What if you could live in any fictional city from a movie?
3. What if you could create a theme park for your favorite show?
4. What if you could be a judge in America’s Got Talent?
5. What if video game characters were cast in Hollywood films?
6. What if you could play a role in F.R.I.E.N.D.S?
7. What if you got your favorite movie prop as a gift?
8. What if you got invited to ‘’The Tonight Show Starring Jimmy Fallon?’’
9. What if you could design clothes under your label for a fashion week?
10. What if you could live in any fictional world?
11. What if you could interview a celebrity for a popular magazine?
12. What if you could form a band with singers from the 80s?
13. What if you could read a book in an hour?
14. What if American celebrities could star in international soap operas?
15. What if ‘’The Simpsons’’ and ‘’The Family Guy’’ had a crossover?
16. What if you could direct the remake of a classic film?
17. What if you could attend the Grammys as a guest? 
18. What if every TV show had a live audience?
19. What if you could perform with a country band for a day?
20.  What if you could experience a day in the life of an actor?
21. What if you could start a pop culture podcast?
22. What if you could rewrite the ending of a movie or a TV show?
23. What if pop stars had to perform only in retro-themed music videos?
24. What if you could livestream your favorite concert?

Funny What If Questions 

Share some funny moments with your team as you answer these funny what if questions. Engage in some light-hearted conversations as you share your take on these hilarious situations.

1. What if you could stop aging physically?
2. What if you could have any superpower for a day?
3. What if you had to live in a house made of Lego bricks?
4. What if you had to crack a joke every time you meet someone new?
5. What if you could only communicate using riddles?
6. What if you had a funny secret talent?
7. What if your hair changed colors according to your mood?
8. What if you had to give a TED talk on a topic you don’t know?
9. What if you had a device that predicts funny moments from the future?
10. What if you had to give up your phone for a week?
11. What if you had to write a grocery list in the form of poetry?
12. What if you had to talk in a made-up funny accent for a day?
13. What if you had a special watch to freeze time?
14. What if your teenage self had written your resume?
15. What if you could pause time whenever you want some rest?
16. What if you could only speak in riddles for a day?
17. What if you had to wear a superhero costume for a day?
18. What if you had to text your friends using emojis for a day?
19. What if you could broadcast your dream on a big screen?
20. What if you could play only one song on repeat?
21. What if you could eliminate an important invention?
22. What if you had to use a typewriter at work?
23. What if you had to trade lives with a cartoon character for a day?
24. What if your pet could give you a parent performance review?

What If Questions on Travel

Bring out the wanderlust personality as you answer a bunch of questions on hypothetical vacation scenarios. Explore a list of some fun what if questions on travel and take some notes from your team’s survival strategy. 

1. What if you could get one free trip anywhere in the world?
2. What if you could pack only three things for a month-long trip?
3. What if you had to update a travel blog after every vacation?
4. What if you had to travel without a camera?
5. What if you could attend Tomorrowland for free?
6. What if you could draft an itinerary for fellow travelers?
7. What if you could explore a new destination every weekend?
8. What if you had to learn a new language before every trip?
9. What if you could go on a road trip with a celebrity you like?
10. What if you could travel to Hogwarts?
11. What if you could only use physical maps to navigate?
12. What if you could only travel to one place with the best hiking trails?
13. What if you are a tour guide in a place you never visited before?
14. What if your travel only involved interacting with the local people?
15. What if you could time travel to your favorite childhood vacation?
16. What if you could live in a different country for every season of the year?
17. What if you had to explore a city on a bicycle?
18. What if you had to stay on a cruise ship for a year?
19. What if you get to experience the life of locals from a remote island?
20. What if you could stay at different hotels every night for a week?
21. What if you could only take a vacation with strangers?
22. What if you had to travel to every country in alphabetical order?
23. What if you could go on unlimited underwater expeditions?
24. What if you could go on a hot air balloon ride in every city you visit?

What If Questions on Food

Food bonds people with a variety of flavors, so why not use this category as a fun ice-breaking session? What if questions on food will challenge you and your team to come up with interesting answers to these unreal culinary situations. 

1. What if you had to eat dessert before every meal?
2. What if your food was prepared by a celebrity chef every day?
3. What if you could eat dishes served during holidays for a month?
4. What if you could host a culinary tasting for the next team-building session?
5. What if you had to invent a fusion dish using three different cuisines?
6. What if you had to cook without electrical appliances for a day?
7. What if someone serves you a delicious meal with an ingredient you don’t like?
8. What if you received the wrong order at a restaurant?
9. What if you had to create a meal using leftovers?
10. What if you could visit a cafe which serves food according to the weather?
11. What if you got to be a Michelin inspector for a day?
12. What if you could invent a new ice cream flavor?
13. What if you could order food from a different country?
14. What if you had to cook every meal from scratch?
15. What if your favorite hangout place closes its door forever?
16. What if you lost taste in all flavors except one?
17. What if you had to eat one cuisine for the rest of your life?
18. What if you get to fulfill your food bucket list in a day?
19. What if you get to try a weird food combo that tastes amazing?
20. What if you had to recreate the best meal you ever had?
21. What if you don’t get your comfort food on a bad day?
22.  What if you could buy only white-colored food?
23. What if you could start an interesting food trend?
24. What if you had to cut off junk food?

Frequently Asked Questions

How can ‘What If’ questions help in team building?

What If questions is a good ice breaker activity that helps to foster open communication and strengthen team bonding. These questions are free virtual team building activities that stimulate creative thinking and provide space for your team to explore different ideas. 

How to answer What If questions?

If somebody asks you a what would you do if question, analyze the scenario and think of an answer that suits the question. For example: if the question is, ‘’ What if all meetings were conducted virtually?’’ You can discuss the pros and cons of the given situation. 

How to play What If questions?

To play what if questions, start by preparing a list of questions across different categories. Introduce the game to your team and start the game by asking a question. Each team member gets to answer the question and share their take on it. To add some fun, vote for the best answers and see who wins.

How to create effective What If questions?

Keep the what if questions clear and easy to understand for active participation from your team. You can also divide the questions into separate categories to cater to different interests and personalities.

How to ensure that the session has enough participation from the team?

To receive maximum participation from the team, create a comfortable space for them to express themselves. Make sure to include questions from popular categories such that your team remains hooked throughout the session.

What are some other question game ideas for an icebreaker session?

Games like Never Have I Ever, Would You Rather, and This or That questions are some of the popular question games to break the ice in a team meeting.