90 Would You Rather Questions for Work

Most of us have pretty dull jobs, and so we have to find ways throughout the working day to keep ourselves entertained, that’s why these Would you Rather questions for work will give you some scenarios to make work life more fun!

In this challenge, you will find some funny questions which are purely for entertainment purposes, a great icebreaker round, and a team-building section.

Take a break from your screen, put on a pot of coffee, and have fun!

Are you ready to start?

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Funny Would You Rather Questions for Work

The words funny and work are not often found in the same sentence, but I think it’s time to change that!

Have you ever imagined what might make the working day more fun and what entertainment your boss could provide you with if only you had control?

I do not recommend trying out 90% of these scenarios in an actual workplace…though I may have done a few in my time!

Are you ready for a giggle?

Let’s go!

Would you rather have a boss who always speaks in rhymes or a coworker who only communicates through interpretive dance?
Would you rather have a job that requires you to wear a clown costume every day or a tutu every day?
Would you rather have a job where you have to sing everything you say or speak in a fake accent all the time?
Would you rather have a boss who constantly tells dad jokes or a coworker who always tells cheesy pickup lines?
Would you rather have a job where you have to work with your arch-nemesis or a job where you have to work with your ex?
Would you rather have a job where you have to wear roller skates all day or to wear flippers all day?
Would you rather have a boss who always talks like Yoda or a coworker who always talks like a pirate?
Would you rather have a job where you have to work with a group of clowns or a group of mimes?
Would you rather have a boss who always wears a tutu or a coworker who always wears a top hat?
Would you rather have a job where you have to speak in pig Latin all the time or in backwards sentences all the time?
Would you rather have a boss who always wears a monocle or a coworker who always wears a fake mustache?
Would you rather have a job where you have to wear a wig every day or a fake nose every day?
Would you rather have a boss who always wears a cape or a coworker who always wears a tiara?
Would you rather have a job where you have to work with a group of clowns or a job where you have to work with a group of magicians?
Would you rather have a boss who always speaks in puns or a coworker who always speaks in riddles?
Would you rather have a job where you have to wear a tutu and a top hat or a job where you have to wear a clown nose and a fake mustache?
Would you rather have a job where you have to work with a group of zombies or a group of aliens?
Would you rather have a boss who always wears a onesie or a coworker who always wears a tutu?
Would you rather have a job where you have to speak in song lyrics all day or to speak in movie quotes all day?
Would you rather have a boss who always wears a sombrero or a coworker who always wears a fez?
Would you rather have a job where you have to work with a group of robots or with a group of ghosts?
Would you rather have a boss who always wears a cowboy hat or a coworker who always wears a tiara?
Would you rather have a job where you have to speak in emojis all day or a job where you have to speak in hashtags all day?
Would you rather have a boss who always wears a superhero costume or a coworker who always wears a princess dress?
Would you rather have a job where you have to work with a group of clowns or a job where you have to work with a group of acrobats?
Would you rather have a boss who always wears a top hat or a coworker who always wears a bow tie?
Would you rather have a job where you have to speak in animal noises all day or a job where you have to speak in baby talk all day?
Would you rather have a boss who always wears a tutu or a coworker who always wears a feather boa?
Would you rather have a job where you have to work with a group of vampires or a job where you have to work with a group of werewolves?
Would you rather have a boss who always wears a tiara or a coworker who always wears a monocle?

Would You Rather Ice Breaker Questions for Work

Don’t you just hate that moment when you’re put in a meeting room and asked to say your name, age, hobbies, etc? I certainly do!

Icebreaker interactions don’t need to be awkward and intimidating anymore!

By playing a round of “would you rather”, you’ll learn more about yourself, employers, employees, and colleagues than you ever would in a normal ‘icebreaker’ situation.

It might also give employers a few pointers on how to improve productivity!

Ready to break the ice?

Would you rather have a job that pays really well but you hate or a job that pays poorly but you love?
Would you rather work for a company that has a strict dress code or a company that has no dress code at all?
Would you rather work in a quiet office or a noisy office?
Would you rather work in a small company with a close-knit team or a large company with lots of different departments?
Would you rather work in a job that requires a lot of travel or a job that requires no travel at all?
Would you rather work in a job where you have to work independently or a job where you have to work as part of a team?
Would you rather work in a job that requires a lot of physical activity or a job that requires a lot of mental activity?
Would you rather work in a job that has a lot of meetings or no meetings at all?
Would you rather work in a job that requires a lot of creativity or a job that requires a lot of organization?
Would you rather work in a job that has a lot of rules or no rules at all?
Would you rather work in a job that requires a lot of communication or a job that requires very little communication?
Would you rather work in a job that has a lot of deadlines or no deadlines at all?
Would you rather work in a job that has a lot of pressure or no pressure at all?
Would you rather work in a job that requires a lot of problem-solving or a job that requires very little problem-solving?
Would you rather work in a job that has a lot of variety or a job that is very repetitive?
Would you rather work in a job that requires a lot of physical labor or a job that requires very little physical labor?
Would you rather work in a job that has a lot of perks or no perks at all?
Would you rather work in a job that has a lot of flexibility or no flexibility at all?
Would you rather work in a job that requires a lot of multitasking or a job that requires very little multitasking?
Would you rather work in a job that has a lot of overtime or no overtime at all?
Would you rather work in a job that has a lot of travel opportunities or no travel opportunities at all?
Would you rather work in a job that requires a lot of customer interaction or very little customer interaction?
Would you rather work in a job that has a lot of training opportunities or no training opportunities at all?
Would you rather work in a job that has a lot of opportunities for advancement or no opportunities for advancement?
Would you rather work in a job that has a lot of technology or very little technology?
Would you rather work in a job that has a lot of paperwork or very little paperwork?
Would you rather work in a job that has a lot of social events or no social events at all?
Would you rather work in a job that has a lot of recognition for good work or no recognition at all?
Would you rather work in a job that has a lot of benefits or no benefits at all?
Would you rather work in a job that has a lot of challenges or no challenges at all?

Would You Rather Questions for Work Team Building

I have always been one of those people who love team-building activities!

There is no better way of discovering people’s strengths and weaknesses and also learning how understanding and encouraging colleagues can be towards one another.

Team building really does bring out the best and worst in people!

This is a fantastic round to play on the bus on the way to a team build activity.

Ready?

Would you rather work in a team where everyone has the same skill set or a team where everyone has different skill sets?
Would you rather work in a team where everyone is very competitive or a team where everyone is very collaborative?
Would you rather work in a team where everyone is very outgoing or a team where everyone is very introverted?
Would you rather work in a team where everyone is very organized or a team where everyone is very creative?
Would you rather work in a team where everyone is very detail-oriented or a team where everyone is very big-picture oriented?
Would you rather work in a team where everyone is very ambitious or a team where everyone is very laid-back?
Would you rather work in a team where everyone is very punctual or a team where everyone is very flexible with time?
Would you rather work in a team where everyone is very decisive or a team where everyone is very open to suggestions?
Would you rather work in a team where everyone is very analytical or a team where everyone is very intuitive?
Would you rather work in a team where everyone is very empathetic or a team where everyone is very objective?
Would you rather work in a team where everyone is very independent or a team where everyone is very interdependent?
Would you rather work in a team where everyone is very risk-averse or a team where everyone is very risk-tolerant?
Would you rather work in a team where everyone is very focused on results or a team where everyone is very focused on process?
Would you rather work in a team where everyone is very good at multitasking or a team where everyone is very good at single-tasking?
Would you rather work in a team where everyone is very good at problem-solving or a team where everyone is very good at conflict resolution?
Would you rather work in a team where everyone is very tech-savvy or a team where everyone is very tech-illiterate?
Would you rather work in a team where everyone is very good at delegation or a team where everyone is very good at taking initiative?
Would you rather work in a team where everyone is very good at time management or a team where everyone is very good at improvisation?
Would you rather work in a team where everyone is very good at communication or a team where everyone is very good at problem prevention?
Would you rather work in a team where everyone is very good at planning or a team where everyone is very good at execution?
Would you rather work in a team where everyone is very good at attention to detail or a team where everyone is very good at big-picture thinking?
Would you rather work in a team where everyone is very good at following rules or a team where everyone is very good at breaking rules?
Would you rather work in a team where everyone is very good at networking or a team where everyone is very good at self-promotion?
Would you rather work in a team where everyone is very good at risk management or a team where everyone is very good at risk-taking?
Would you rather work in a team where everyone is very good at innovation or a team where everyone is very good at optimization?
Would you rather work in a team where everyone is very good at conflict management or a team where everyone is very good at conflict avoidance?
Would you rather work in a team where everyone is very good at problem identification or a team where everyone is very good at problem resolution?
Would you rather work in a team where everyone is very good at data analysis or a team where everyone is very good at intuition?
Would you rather work in a team where everyone is very good at customer service or a team where everyone is very good at product development?
Would you rather work in a team where everyone is very good at brainstorming or a team where everyone is very good at decision-making?