Using ‘Would You Rather’ questions with your team is a fun way to inspire conversations at work.
They present two extreme situational options which requires the person to choose and explain their position…
‘Would You Rather’ questions help by inspiring laughter and conversation at work.
The interesting discussions and debates between coworkers that result from introducing these “forced choice” options can increase employee morale and strengthen connections.
You can use this list of questions as a fun and unexpected addition to your next virtual team meeting, or as an occasional part of your office teambuilding efforts.
How to Actually Use These Questions So They Do Something
Most teams use questions like these as filler. Someone reads one out loud, three people answer, everybody laughs, and the meeting moves on.
Nothing wrong with that. Laughter is good for a team.
But if you want these questions to do more than pass two minutes, you have to run them with a little more intention.
Here is what I do when I facilitate these with a group:
Ask for the why, not just the answer. The answer is entertainment. The reason behind the answer is where you learn something about a teammate. Pirate or ninja tells you nothing. Why someone picked ninja tells you they value working quietly and being underestimated.
Let people disagree out loud. The best moments come when two people pick opposite answers and have to defend them. That low stakes friendly disagreement builds the exact muscle your team needs for higher stakes disagreements later.
Go around in a different order every time. If you always start with the same person, the same people dominate. Start with someone different, and start with someone quiet.
Use one question, not ten. One question with real conversation beats ten questions with quick answers. You are not trying to get through a list. You are trying to get people talking.
Do it before the agenda, not after. Teams that connect first make better decisions. Teams that save connection for the end never get to it because the meeting runs long.
- Would you rather time travel back to the past or to the future?
- Would you rather give up brushing your hair or brushing your teeth for a year?
- Would you rather be able to read minds or be invisible?
- Would you rather only be able to whisper or only be able to shout?
- Would you rather meet your great-great-grandmother or your future granddaughter?
- Would you rather live without music or movies for the rest of your life?
- Would you rather have the ability to understand every language or talk to animals?
- Would you rather win a Nobel Prize or an Oscar?
- Would you rather never get tired or never have to go to the bathroom?
- Would you rather compete in a summer Olympic sport or a winter Olympic sport?
- Would you rather be the oldest person in the office or the youngest?
- Would you rather give up bathing for a month or give up the internet for a month?
- Would you rather permanently live 500 years in the future or 500 years in the past?
- Would you rather be in a monthly fight club or a weekly book club?
- Would you rather lose the ability to read or lose the ability to speak?
- Would you rather have a huge imagination or a photographic memory?
- Would you rather live in a world where there is no crime or no privacy?
- Would you rather give up pizza or give up ice cream?
- Would you rather have to grow your own food or sew all your clothes?
- Would you rather be a captain of a ship or an airplane pilot?
- Would you rather all your future meetings be online or face to face?
- Would you rather be famous for all the wrong reasons or not famous at all?
- Would you rather get three solid months of vacation or get one day off every week?
- Would you rather have a terrible boss but a great job or a great boss but a terrible job?
- Would you rather commute two hours to a dream job or two minutes to a boring job?
- Would you rather your skin be blue like a Smurf or green like Shrek?
- Would you rather be a pirate or a ninja?
- Would you rather never be able to leave the US or travel and never be able to return?
- Would you rather work in an office where you’re paid per hour or per task?
- Would you rather have a tail or horns?
- Would you rather have a job where you talk to people all day or talk to nobody all day?
.
.
Five Questions That Work Best in a Work Setting
Not every question on this list belongs in every room. If you only have time for one, these five tend to produce the most useful conversation with a work team:
Would you rather have a terrible boss but a great job or a great boss but a terrible job?
This one surfaces what people actually value about their work. Some people are motivated by the task. Some are motivated by the relationship. Knowing which is which changes how you lead them.
Would you rather all your future meetings be online or face to face?
Every hybrid team has an unspoken disagreement about this. Better to have it out loud with laughing than to let it simmer.
Would you rather have a job where you talk to people all day or talk to nobody all day?
This is a personality style conversation hiding inside a silly question. Your outgoing people and your reflective people will split cleanly, and the whole team gets a reminder that both types are on the roster.
Would you rather work in an office where you’re paid per hour or per task?
People reveal how they think about accountability. Some want their effort recognized. Some want their output recognized. That distinction shows up in every performance conversation you will ever have.
Would you rather be the oldest person in the office or the youngest?
Multigenerational teams rarely talk about generational dynamics directly. This gives them a side door into it.
Have fun using these questions to spark conversation
(DOWNLOAD A PDF OF THIS “WOULD YOU RATHER” LIST HERE)
Sometimes just adding a bit of light conversation is just what a team needs.
And if you want to improve collaboration, trust, and accountability in your organization, planning a more intentional corporate team building event may be a valuable idea.
Team building is more than just recreational FLUFF or silly activity.
Real team building involves profitable fluff – an ongoing commitment to create meaningful connections in your organization.
Great leaders ensure that everyone understands and cares about how they are contributing to a compelling common goal… and they ensure that everyone understands and appreciates the strengths and team personality types of the people they are working with.
A healthy, positive, and profitable workplace culture begins with those two connections.
Fun Is a Start, Not a Strategy
I want to be straight with you about what these questions can and cannot do.
They can break tension. They can help a quiet person say something out loud. They can remind a team that the people on the other end of the video call are actual humans.
What they cannot do is fix a team where expectations are unclear, accountability is inconsistent, or trust has already eroded.
I have walked into plenty of organizations where leaders had tried the icebreakers, the happy hours, the escape room, and the ropes course, and were frustrated that nothing changed on Monday morning.
The activity was never the problem.
The problem was that the activity was not connected to anything.
Culture is the set of behaviors that are allowed and repeated. If you want different behaviors, people need a new experience that creates new awareness, and then a leader who reinforces it consistently after the fun is over.
That is the difference between a recreational activity and a real team building event.
Use the questions. Have the laugh. Then decide whether your team needs something more than a laugh.
What Might Also be Helpful…
If the fun stuff is not moving the needle, the Sticky 11 checklist is the next step.
I wrote the Sticky 11 checklist because I kept watching leaders let culture drift.
Not from a lack of intent. From a noisy week.
The small things that hold a team together are always the first things to go when the calendar fills up.
So I pulled eleven habits out of my leadership parables and speaking programs and stripped them down to something a leader can run in five minutes on a Friday:
You can grab the FREE weekly leadership checklist HERE.
