50 Thought-provoking Would You Rather Questions for a Fun Team-building Session

Have you ever thought about how you and everybody you know would respond to unusual choices? ‘Would You Rather’ questions for work allow people to skip the small talk and communicate freely. The situations can be funny, weird, or difficult, and employees get to know each other better as they find out each other’s preferences in various situations. Check out our list of 50 thought-provoking Would You Rather questions for a fun team-building session!

1. What are Would You Rather Questions?

‘Would You Rather’ questions poses a dilemma with two situations which are often extreme, and it requires the person to choose one of two situations (they are not allowed to be neutral about it). The choices can be:

  • Attractive – “Would you rather only have money or only have fame?”
  • Exciting – “Would you rather only have the superpower to fly or only have the superpower to be invisible?”
  • Funny – “Would you rather eat only chips for one year or not be able to eat chips for one year?”

‘Would You Rather’ questions help in improving team dynamics at work. The rationales for choosing a situation spark interesting conversations and debates amongst coworkers and increase employees’ engagement. You can also play it as a virtual team-building game or a group exercise where members take turns in asking questions. Keep in mind to make the questions safe for work and non-triggering, yet funny and quirky at the same time!

2. Would You Rather Questions for Work

2.1 General Work Questions

2.1.1 Would you rather only have super fast typing speed or only be able to read ridiculously fast?

2.1.2 Would you rather always be 10 minutes late to work or always be 20 minutes early to work?

2.1.3 Would you rather take an all-expenses-paid dream vacation for a month every year at a mediocre job or have your dream job but pay for your vacations yourself?

2.1.4 Would you rather only have a constant supply of the best coffee or only have a constant supply of the best snacks at your office?

2.1.5 Would you rather work four-day weeks with long work hours or six-day weeks with short work hours?

2.1.6 Would you rather work in an office for the rest of your life or work remotely for the rest of your life?

2.1.7 Would you rather work a mediocre job and be the best at Microsoft Excel or work at your dream job and be poor at Microsoft Excel?

2.1.8 Would you rather be in charge of the food committee or be in charge of games arrangements for an office party?

2.1.9 Would you rather have your salary come in on the first day of the month or the last day of the month?

2.1.10 Would you rather only be able to have your video on during an office conference call or only be able to have your video off during an office conference call?

2.2 Questions for Coworkers

2.2.1 Would you rather only be able to move to a new city every month or never be able to leave the city you were born in?

2.2.2 Would you rather instantly become a successful startup founder or instantly become a CEO of a major company?

2.2.3 Would you rather always sit by the printer or always sit by the water cooler at the office?

2.2.4 Would you rather be the best in the world at a skill or job of your choice but have no work-life balance or be mediocre at work and have a great work-life balance?

2.2.5 Would you rather work an extra hour and get two hours of break time or work with no breaks and leave the office an hour early?

2.2.6 Would you rather live ten minutes away from a mediocre job or commute two hours to your dream job?

2.2.7 Would you rather work at a really fancy office or work at an office where you could wear pajamas to work?

2.2.8 Would you rather get paid a year’s salary at once or get paid in installments throughout the year?

2.2.9 Would you rather work for a startup for the rest of your life or work for a multinational corporation for the rest of your life?

2.2.10 Would you rather give up eating pizzas with your team or give up eating birthday cakes with your team?

2.3 Questions for Team Building

2.3.1 Would you rather always be the leader or always follow the leader?

2.3.2 Would you rather always have a team lunch or always have a team dinner?

2.3.3 Would you rather always be the host of a team-building activity or always be a participant in a team-building activity?

2.3.4 Would you rather have Batman in your team or Superman in your team?

2.3.5 Would you rather have a group activity indoors or outdoors?

2.3.6 Would you rather be a part of a smaller team or a larger team?

2.3.7 Would you rather only be able to choose the participants for your team for the rest of your life or only get picked for a team for the rest of your life?

2.3.8 Would you rather only be able to go first in a team game or only be able to go last in a team game?

2.3.9 Would you rather team up with your boss in a game or go head-to-head with them in a game?

2.3.10 Would you rather be the team lead for a year or never be a team lead for the rest of your life?

2.4 Silly Questions

2.4.1 Would you rather give up brushing your hair for the rest of your life or brushing your teeth for the rest of your life?

2.4.2 Would you rather be in the real-life version of Squid Game or The Walking Dead?

2.4.3 Would you rather wear your partner’s clothes for a month or let them pick your work outfits for a month?

2.4.4 Would you rather only be able to watch only one OTT show for the rest of your life or only be able to watch the first episode of any OTT show for the rest of your life?

2.4.5 Would you rather get a paper cut on your finger or stub your pinky toe?

2.4.6 Would you rather have a helium-inhaled voice every time you’re having a serious conversation with someone or laugh every time someone cries?

2.4.7 Would you rather have a hamster-sized cat or a cat-sized hamster?

2.4.8 Would you rather always have bad breath or always have smelly feet?

2.4.9 Would you rather have the ability to talk to animals or have the knowledge of everything in the world?

2.4.10 Would you rather be only able to go to a specific year into your past for 10 minutes or a specific year into your future for 10 minutes?

2.5 Tricky Questions

2.5.1 Would you rather only have ears that record everything or only have eyes that film everything?

2.5.2 Would you rather only be able to go out during the day or only be able to go out during the night?

2.5.3 Would you rather have a full-time personal chef or become a gourmet chef yourself instantly and cook your own meals?

2.5.4 Would you rather only be able to visit space or only be able to explore the depths of the sea?

2.5.5 Would you rather never be able to watch your favourite movie again or never be able to listen to your favourite music album again?

2.5.6 Would you rather lose the ability to use digital payments or lose the ability to use GPS for the rest of your life?

2.5.7 Would you rather only be able to control fire or only be able to control water?

2.5.8 Would you rather lose the ability to use social media or lose the ability to use search engines?

2.5.9 Would you rather only live on the beach for a year or only live in a cabin in the woods for a year?

2.5.10 Would you rather only be able to do leg exercises for the rest of your life or only be able to lift weights for the rest of your life?

3. FAQs

3.1 What are some funny Would You Rather questions for work?

Here are some funny would you rather questions for work:-

3.1.1 Would you rather give up using deodorant for a year or give up using toothpaste for a year?

3.1.2 Would you rather be friends with Dwayne Johnson or Keanu Reeves?

3.1.3 Would you rather always have ice cream toppings on pizza or always have pizza toppings on ice cream?

3.1.4 Would you rather only have telepathy or only have telekinesis?

3.2 What are some difficult Would You Rather questions?

Here are some difficult would you rather questions:-

3.2.1 Would you rather have an unlimited petrol/ gas supply to your car or have unlimited data on your mobile phone?

3.2.2 Would you rather always be able to visit tropical vacations spots or only be able to visit cold vacation destinations?

3.2.3 Would you rather never be able to remember someone’s name or never be able to remember directions?

3.2.4 Would you rather never be able to speak a second language or never be able to play an instrument?


Aakash GuptaAakash Gupta
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Aakash Gupta

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