71 Unique Would You Rather Questions For Work

Would you rather questions are a great way to spark conversation and offer some insights into your colleagues’ preferences and personalities.

They’re great for fun icebreakers when introducing new people, or as a way to mix things up and insert some energy into your regular team meetings.

Here are my top would you rather questions for work meetings and team building events:

General Work Preferences

1. Would you rather work from home or work in the office every day?
2. Would you rather have a short, intense workday or a longer, more relaxed one?
3. Would you rather have a big office with a window or a smaller, more private workspace?
4. Would you rather have unlimited vacation days or a higher salary?
5. Would you rather work on a single long-term project or multiple short-term projects?
6. Would you rather work in a large company or a small startup?
7. Would you rather work under a manager who micromanages or one who is totally hands-off?
8. Would you rather have a job with high pay but lots of stress or low pay with no stress?
9. Would you rather work in a team where everyone is very serious or where everyone is very relaxed?
10. Would you rather work in a noisy environment with lots of energy or a quiet, focused one?

Professional Development

1. Would you rather receive a promotion without a raise or a raise without a promotion?
2. Would you rather get a bonus based on individual performance or team performance?
3. Would you rather have job security in a role you don’t love or risk it for a dream job?
4. Would you rather have a mentor or be a mentor?
5. Would you rather attend a networking event or a skills development workshop?
6. Would you rather have a role with clear expectations or one with flexibility to define your own?
7. Would you rather work with cutting-edge technology or tried-and-true methods?
8. Would you rather work for a company known for innovation or one known for stability?
9. Would you rather specialize in one skill or be a generalist in many?
10. Would you rather have a fast track to management or become an expert in your field?

Office Culture

1. Would you rather have a boss who’s always joking or one who’s always serious?
2. Would you rather have weekly team-building activities or monthly social events?
3. Would you rather work in a company with a strict dress code or one with no dress code at all?
4. Would you rather have free snacks or a company-sponsored gym membership?
5. Would you rather work in an office where everyone is friends or where everyone is professional?
6. Would you rather have a company retreat in the mountains or at the beach?
7. Would you rather celebrate your work anniversary with a personal gift or a team party?
8. Would you rather have casual Fridays or flexible working hours?
9. Would you rather work in a place that values tradition or one that embraces change?
10. Would you rather be the youngest or the oldest person on your team?

Productivity and Work Style

1. Would you rather have an hour of focused work or two hours of interrupted work?
2. Would you rather attend back-to-back meetings or work on a tight deadline?
3. Would you rather be over-prepared or under-prepared for a meeting?
4. Would you rather start work early and finish early or start late and finish late?
5. Would you rather have a day full of meetings or a day full of tasks?
6. Would you rather work on a project alone or with a team?
7. Would you rather work on creative tasks or analytical tasks?
8. Would you rather brainstorm ideas in a group or on your own?
9. Would you rather work on a detailed plan or execute a broad vision?
10. Would you rather have a cluttered desk or a cluttered email inbox?

Career Path

1. Would you rather have a career that’s fulfilling but not well-paying or one that’s high-paying but unfulfilling?
2. Would you rather work in the same job for your entire career or change jobs every few years?
3. Would you rather climb the corporate ladder or stay in a comfortable position?
4. Would you rather lead a project with a tight deadline or be part of a team with a relaxed timeline?
5. Would you rather have a job with lots of travel or one where you stay in one place?
6. Would you rather work for a company with a great reputation or one with great benefits?
7. Would you rather be known for your creativity or your work ethic?
8. Would you rather be the go-to person for help or the person who gets things done quickly?
9. Would you rather switch careers completely or stick with the same industry for life?
10. Would you rather take on a role with lots of responsibility or one with less pressure?

Relationships at Work

1. Would you rather work with a difficult client who pays well or an easy-going client who pays less?
2. Would you rather have a friendly colleague who talks too much or a quiet one who’s hard to get to know?
3. Would you rather give a presentation to your team or to upper management?
4. Would you rather receive constructive criticism in private or in a group setting?
5. Would you rather work closely with your boss or have more independence?
6. Would you rather have a boss who gives you lots of feedback or one who gives very little?
7. Would you rather work in a team where everyone contributes equally or one where some people do more work?
8. Would you rather have a colleague who is always late or one who always leaves early?
9. Would you rather be the person who delegates tasks or the one who gets things done?
10. Would you rather work in a competitive environment or a collaborative one?

Fun and Unique

1. Would you rather win the employee of the month every month or have one amazing bonus at the end of the year?
2. Would you rather be stuck on a project with no guidance or with too much guidance?
3. Would you rather never have to attend another meeting or never have to write another report?
4. Would you rather work in an office with no coffee or no air conditioning?
5. Would you rather be the one who always brings snacks or the one who always eats them?
6. Would you rather have to wear business attire every day or pajamas?
7. Would you rather have a co-worker who never stops emailing you or one who never replies?
8. Would you rather attend a mandatory team-building exercise or skip it and work overtime?
9. Would you rather have a colleague who is a perfectionist or one who is very laid back?
10. Would you rather get along with everyone but not be very productive or be highly productive but not liked by everyone?
11. Would you rather have a job where you can take a nap every day or one where you get free lunch every day?