Most Likely To Questions for Work
For team leads, organizers and anyone asked to run a warm-up for coworkers at a meeting, a team-building session or an away day. The prompts are grouped into office life, meetings and messages, remote work, teammates, hidden talents and away day, and every one is a compliment or a harmless quirk, so nobody is voted worst at anything. Each has a note on what to do after the vote so the person named gets a good moment.
One at a time · 01 of 104
Office life
“Who is most likely to know where the good scissors, the spare batteries and the tape actually live?”
Why ask it
Every workplace has one person who is the map. Once the vote is in, quiz them on the most obscure item anyone can think of, then thank them for all the times they got up to point.
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The questions
Each question, and why to ask it
Office life
Who is most likely to know where the good scissors, the spare batteries and the tape actually live?
Why ask it
Every workplace has one person who is the map. Once the vote is in, quiz them on the most obscure item anyone can think of, then thank them for all the times they got up to point.
Who is most likely to bring in homemade baking on an ordinary Tuesday for no reason at all?
Why ask it
Requests are the reward here, so let the room call out what it wants in the next batch. On a team with no bakers, the vote goes to whoever turns up with the good pastries.
Who is most likely to know every teammate's coffee or tea order by heart?
Why ask it
Put it to the test with three orders from people in the room. A correct answer gets applause, and a wrong one gets a correction they will not need twice.
Who is most likely to say good morning on a Monday and sound like they mean it?
Why ask it
Best at the top of a Monday meeting, when the evidence is minutes old. They can explain what they know about Mondays that everyone else is missing, and nobody is obliged to believe it.
Who is most likely to refill the printer paper before it runs out on somebody else?
Why ask it
A job nobody sees when it is done well, which makes the vote itself the thanks. Say so in plain words, then check whether they can clear a paper jam too, and book them for the next one.
Who is most likely to have a favorite mug that everybody knows not to borrow?
Why ask it
Skip the jokes about what happens to borrowers and go to the mug itself: where it came from and how long it has been on the job. On a call, it gets held up to the camera.
Who is most likely to have a desk plant that is doing better than everyone else's?
Why ask it
Offer the gardener a new title: plant sitter for the whole floor during vacations. Whether they accept tells the team who to leave a watering can with.
Who is most likely to get a birthday card signed by the entire team without the birthday person noticing?
Why ask it
Count how many cards they have smuggled around the building this year. Then check when their own birthday is, since the person who runs the cards is the easiest one to forget.
Who is most likely to turn a lunch order for twelve people into a smooth operation?
Why ask it
There is a method, and the room should hear it: the shared list, the firm cutoff, or a flat refusal to accept 'anything is fine' as an order. Colleagues who tried it once and gave up can lead the applause.
Who is most likely to greet everyone in the building by name, from the front desk to the delivery driver?
Why ask it
No test and no joke after this one. Say out loud that people have noticed, because someone who does this out of habit may not know it stands out.
Who is most likely to have the desk where people stop to chat on their way past?
Why ask it
Regular visitors can own up to how often they take the long way around on purpose. For a hybrid team, the remote version is the colleague whose quick messages always turn into a conversation.
Who is most likely to own a label maker and use it on everything within reach?
Why ask it
Two quick questions: the last thing that got a label, and the strangest. Then the team nominates one object in the room that still needs one and leaves the wording to the expert.
Who is most likely to know the best lunch within a five-minute walk?
Why ask it
Get one recommendation and the exact order, then set a date for the team to go. A vote that ends with a lunch plan has done its job.
Who is most likely to give names to the printer, the coffee machine and the slow elevator?
Why ask it
If the names have stuck, say so, because that is the compliment. Then pick one piece of equipment that is still anonymous and hold a christening.
Who is most likely to leave a drawing on the whiteboard that nobody has the heart to erase?
Why ask it
Strongest on a team where one doodle has already outlived several meetings. Pass the artist a marker for a new one, and get the room to promise it stays up.
Who is most likely to give a visitor a better tour than the official one?
Why ask it
Which stop is on their tour that no official one includes? A window, a shortcut, a particular vending machine: whatever they pick says what they like about the place.
Who is most likely to have built the spreadsheet that the whole team now runs on?
Why ask it
Whoever leans on that spreadsheet hardest should describe a week without it. Its builder then gets to name the formula they are proudest of, and should be allowed the full explanation.
Who is most likely to try the new software first and write the how-to for everyone else?
Why ask it
The how-to is the generous half, so thank them for that part specifically. When the next system arrives the team knows whose guide to wait for, and its author deserves fair warning.
Meetings and messages
Who is most likely to find the perfect GIF within three seconds of a message landing?
Why ask it
Speed and taste are both on trial, so run the trial: invent an announcement, post it in the team chat and give them ten seconds. Everyone else scores the result out of ten.
Who is most likely to end a meeting ten minutes early and get thanked for it?
Why ask it
What is the sentence they use to wrap things up? Get the exact wording, because it is the one part anybody else who runs a meeting can borrow by this afternoon.
Who is most likely to send the notes and next steps before people are even back at their desks?
Why ask it
Do they type during the meeting or write it all up from memory afterward? Either answer impresses people, and a thank-you from whoever relies on those notes most finishes it off.
Who is most likely to write a message so clear that nobody needs to ask a follow-up?
Why ask it
Clear messages look effortless and are not. Get one rule they write by, such as putting the request in the first line, and watch for colleagues trying it in the chat later the same day.
Who is most likely to react to every announcement with a full row of emoji?
Why ask it
Before they say a word, the group guesses their signature emoji. Then tell them what is true: an announcement with six reactions under it feels far better to have posted than one that lands in silence.
Who is most likely to drop a pun in the team chat that makes everyone groan and then repeat it all week?
Why ask it
The repeating proves it worked. Have a colleague quote the one that lasted longest, then allow a single fresh attempt and groan as loudly as it deserves.
Who is most likely to ask "what problem are we solving?" at exactly the right moment?
Why ask it
Introduce it as the question that saves an hour, so nobody hears it as the question that interrupts. How they can tell the moment has come is the part worth asking about.
Who is most likely to build slides so tidy that people ask for the template?
Why ask it
One rule they follow on every slide, given away for free, is the right price for this award. If the template really is in demand, agree where it will be shared before moving on.
Who is most likely to reach an empty inbox on a Friday afternoon and take a screenshot of it?
Why ask it
A screenshot counts as evidence if they have one. Anyone who wants to can call out their own unread count, purely so the champion can enjoy the gap, and nobody is made to.
Who is most likely to make sure the quietest person in the meeting gets asked what they think?
Why ask it
Read the result out straight, with no joke attached. Do not ask for a demonstration or point out who the quiet colleagues are: hearing that the habit has been noticed is the whole reward.
Who is most likely to explain an acronym before anyone has to admit they do not know it?
Why ask it
Newer colleagues tend to vote fastest on this one. Afterward, anyone willing can confess a term they nodded along to for months, starting with the most senior person present.
Who is most likely to sketch a diagram that finally gets the whole room on the same page?
Why ask it
Name the specific meeting if you can, because the person may not know which drawing made the difference. Then find out whether they think in pictures or only reach for the marker when words stall.
Who is most likely to answer a quick question with a link, a screenshot and an arrow pointing at the right button?
Why ask it
The arrow is the detail to praise: someone spent ten extra seconds so a colleague would not have to hunt. Whoever asked them the last quick question can say how long it would have taken alone.
Who is most likely to write an out-of-office reply that people enjoy reading?
Why ask it
A past reply recited from memory starts things off. After that, everyone gets two minutes to draft their own and the champion judges.
Who is most likely to have a catchphrase the whole team now uses?
Why ask it
On three, everyone says the phrase together. Its owner may have had no idea it had spread that far, and their face at that moment is the prize.
Who is most likely to volunteer to go first when the room goes quiet?
Why ask it
Going first is a favor to everyone who was dreading it, and it is rarely called one. Their prize is the right to choose who goes first at the next meeting.
Who is most likely to carry on calmly from memory when the slides refuse to load?
Why ask it
The applause is for the calm more than the memory. Colleagues who were in the room when it happened should describe it, since the presenter was too busy to see how unbothered they looked.
Who is most likely to keep a thread of good news going in the team chat?
Why ask it
Start a round of it right now: one piece of good news from the person named, then one from each colleague, about work or anything else. Hold everyone to a sentence so it stays a warm-up.
Remote work
Who is most likely to have a pet stroll across the keyboard and steal the whole call?
Why ask it
On video, the pet gets brought into frame for a formal introduction, name and job title included. In a room, a photo passed around on a phone draws the same noise.
Who is most likely to make an excellent point while still on mute?
Why ask it
Expect a tie and a lot of people voting for themselves, since nobody is innocent. The follow-up is the best sentence anyone here has ever lost to the mute button.
Who is most likely to change their virtual background to match the topic of the meeting?
Why ask it
Challenge them to find one for this meeting before the next prompt is read. If nobody on the team does this yet, treat the vote as a prediction that someone now has until Friday to live up to.
Who is most likely to have a shelf behind them that people try to read during calls?
Why ask it
The shelf's owner picks one thing from it to show, and only that. Leaving the choice with them keeps a curious team from turning the prompt into a tour of somebody's home.
Who is most likely to work from a different spot every day, from the porch to the public library?
Why ask it
A top three, with what each spot is good for, is the thing to request. An answer like 'writing on the porch, calls in the parked car' is the kind that gets copied.
Who is most likely to have a desk setup with more screens than seems strictly necessary?
Why ask it
Sixty seconds for a tour, shown or described, and the time limit matters because they could happily fill ten minutes. Close by asking what the next upgrade is.
Who is most likely to be wearing slippers under the desk right now?
Why ask it
Take their word for it. Nobody tilts a camera to prove anything, and a spoken description of the slippers gets a bigger laugh than the sight of them would.
Who is most likely to take a call on a walk and come back with the best idea of the day?
Why ask it
Where does the route go, and which idea came back from it? If the story is a good one, propose that one call this week is taken on foot by anyone who wants to.
Who is most likely to cook a proper lunch from scratch between two meetings?
Why ask it
Today's menu, please, in full. Everyone who ate crackers over a keyboard gets to be openly jealous, and the cook gets to enjoy it.
Who is most likely to wave goodbye at the end of every single video call?
Why ask it
A wave ends a call warmly, where the alternative is a row of faces hunting for the leave button. Honor the vote at the end of today's call: everybody waves out together.
Who is most likely to fix a teammate's audio problem over chat in under a minute?
Why ask it
Which fix works most often? Have it typed into the chat and pinned where the team can find it, so the next person with a silent microphone can try it before sending for help.
Who is most likely to know what time it is for every person on the team without looking it up?
Why ask it
Quiz them on two or three colleagues in other time zones. It is a bigger compliment than it sounds, because this is the person who never books a meeting at someone else's dawn.
Who is most likely to own a standing desk and really stand at it?
Why ask it
The joke lands on everybody else, whose standing desks have been sitting down for months. How long does the champion last each day? Count the guilty looks while they answer.
Who is most likely to share their screen with every tab already open in the right order?
Why ask it
Is it a ritual before every meeting, or does their screen simply always look like that? Either way, thank them on behalf of everyone who has watched a presenter search for the right window.
Who is most likely to set up a virtual coffee with a colleague they have not talked to in a while?
Why ask it
Who was the last one with, and who is next? If someone on the call says they would like an invitation, the vote has arranged a coffee, which beats applause.
Who is most likely to send the recording to whoever missed the call, with the important minute marked?
Why ask it
The marked minute is the thoughtful part, so name it. Anyone who was spared an hour of video by that timestamp can say thank you now, out loud or in the chat.
Teammates
Who is most likely to drop what they are doing to help with a problem that is not theirs?
Why ask it
Slow the game down here and take two or three examples from the room. The person named may have no idea how many colleagues are carrying a story about them.
Who is most likely to notice you are having a rough day and quietly put a coffee on your desk?
Why ask it
Nobody has to say what the rough day was about. One thank-you from someone who found that coffee on their desk is the whole moment, and a joke would only get in its way.
Who is most likely to share the credit with the whole team when they are the one being praised?
Why ask it
The fair reply is to hand the credit back. Go around the voters and collect one thing each that this person did and never claimed.
Who is most likely to make a stressful week feel lighter just by being in the room?
Why ask it
Easy to vote on and hard to explain, so make the group try. What is it they do? Expect small things, a tone of voice or a habit of asking, which the person may be hearing listed for the first time.
Who is most likely to remember the name of your dog, your kid or your favorite team and ask after them?
Why ask it
Return the compliment: how much can the group recall about the rememberer's own pets, people and teams? If the answers come out thin, the team has homework.
Who is most likely to ask how your weekend was and then really listen to the answer?
Why ask it
Try it live. They ask one volunteer about the weekend while everybody else listens for the second question, because the second question is where the listening shows.
Who is most likely to teach you a shortcut that saves an hour every week?
Why ask it
The prize is a one-minute lesson, taught immediately. They get to be the expert, and everyone goes back to work with a trick they did not have when the game started.
Who is most likely to celebrate a colleague's win louder than their own?
Why ask it
Turn it around for once. They name something of their own that went well lately, and the team cheers at the volume this person normally supplies for others.
Who is most likely to be the first person a new hire is told to go and talk to?
Why ask it
Recent joiners can confirm the result or overturn it. What does this person always say to someone in week one? Long-serving colleagues should hear it as well, in case the advice has changed.
Who is most likely to send a thank-you after a project that names exactly what each person did?
Why ask it
Does anyone still have one of those messages saved? A single line read aloud by its recipient shows the writer what becomes of their thank-yous after they are sent.
Who is most likely to say "let me find out" and come back with the answer the same day?
Why ask it
Reliability almost never gets its own award, so announce this like one. The useful follow-up is practical: where do they write a promise down so it survives until the end of the day?
Who is most likely to give feedback so kindly that you end up thanking them for it?
Why ask it
Ask only for the sentence they open with. Keep it general: nobody's actual feedback should be replayed in front of the team, however well the conversation went.
Who is most likely to settle a tense moment with one well-timed joke?
Why ask it
Timing is the talent being voted on, more than being funny. Does the line get planned, or does it just arrive? Leave the tense meeting itself unnamed, since someone present may have been the tense part.
Who is most likely to know the story behind why something is done the way it is?
Why ask it
Choose one odd process the team follows and request its origin story. A memory that long is what stops a team from rerunning an experiment that already failed once.
Who is most likely to make a new idea sound possible before anyone lists why it cannot work?
Why ask it
Thank them on behalf of every half-formed idea that survived its first meeting. Then ask which idea they are glad they spoke up for.
Who is most likely to forward an article or a course with the words "this made me think of you"?
Why ask it
Those words mean somebody was keeping a colleague's goals in mind while reading. People who have received one can say what it was, and admit whether they ever opened it.
Who is most likely to coach a newer colleague for months without ever calling it mentoring?
Why ask it
Watch who points first, because it is probably the person being coached. They get the floor for one thing they learned, which their unofficial mentor may never have heard said.
Who is most likely to have a customer ask for them by name years later?
Why ask it
For teams that deal with customers, clients, patients or students, and worth swapping the word to fit. A colleague should tell the story of the nicest thing a customer said, because the person it was said about will play it down.
Who is most likely to win the office quiz on a category nobody saw coming?
Why ask it
The group guesses the category first, then the expert reveals it. One test question follows, set by whichever colleague believes they know the subject just as well.
Who is most likely to speak more languages than the team realizes?
Why ask it
Let them count the languages off themselves and, only if they feel like it, say good morning in each. Two colleagues sometimes find out at this point that they share one.
Who is most likely to carry a tiny toolkit and fix the wobbly table before the meeting starts?
Why ask it
What is in the kit, and what did it last rescue? Any wobbling table or squeaking chair within sight of this meeting has just found its repair person.
Who is most likely to have had the most surprising job before this one?
Why ask it
Run it as a second vote: each nominee offers one past job of their own choosing and the room picks the biggest surprise. Nobody is asked to list everything they have ever done.
Who is most likely to make something by hand that people would happily pay for?
Why ask it
Knitting, woodwork, pottery, bread: whatever it is, a photo on a phone does more than a description. Be ready for a colleague to try to place an order on the spot.
Who is most likely to finish the crossword before their coffee has cooled?
Why ask it
Which puzzle is the daily one, and what is their best time? Asking it tends to bring every other solver on the team out of hiding, and a lunch table may form.
Who is most likely to play an instrument well enough to join a band tomorrow?
Why ask it
Once the instrument is known, cast the other band members from the team: who sings, who drums, who drives the van. A colleague who has kept quiet about a guitar may speak up.
Who is most likely to have a sports medal in a drawer that they have never mentioned?
Why ask it
Confirm or deny, and both answers are accepted. A real medal comes with a real day, so get the event, the year and who was there to watch.
Who is most likely to do a spot-on impression of a cartoon character?
Why ask it
Cartoon characters and famous voices only, never colleagues or the boss. One short line is plenty, and only from someone who is visibly keen to deliver it.
Who is most likely to have been on television, on stage or in a newspaper without ever bringing it up?
Why ask it
Telling it is their choice, and 'yes, and that is all I am saying' is a complete answer. Leave room for a second colleague to announce that they have one too.
Who is most likely to do the math in their head before anyone has opened a calculator?
Why ask it
Test it with the bill for an imaginary team lunch, split nine ways with a tip. Applaud the answer whether or not anybody in the room can check it.
Who is most likely to pull off a magic trick with whatever is on the table?
Why ask it
A real magician gets the choice: one trick now, or a booking for the next gathering. If the vote was only a hunch, hand over a coin and thirty seconds, and clap for the attempt.
Who is most likely to grow vegetables and bring in the surplus for the team?
Why ask it
Ask what is growing at the moment and what did best last year. Any other gardeners on the team will want to compare notes on tomatoes, so decide beforehand how long that conversation gets.
Who is most likely to write a funny poem for a colleague's farewell card?
Why ask it
Commission one on the spot: a subject that is not a person, such as the coffee machine or the Monday meeting, and a few minutes to write while the game carries on. The poem gets read out at the end.
Who is most likely to name any song from its first three seconds?
Why ask it
Easy to check with a phone and a playlist. Three songs, three seconds each, and the champion either defends the title or hands it to whoever got there faster.
Who is most likely to collect something unexpected, such as old maps, board games or rare sneakers?
Why ask it
Three questions cover it: how many, which was hardest to find, and which one they would rescue first in a flood. Then stand back, because a collector does not often get an audience.
Who is most likely to keep the whole team fed, warm and entertained if we got snowed in at the office overnight?
Why ask it
Votes tend to split between whoever would find the food, whoever would organize the blankets and whoever would run the games. Appoint all three, and the team has an emergency plan it will never need.
Away day
Who is most likely to be first on the dance floor at the team party?
Why ask it
Somebody has to go first or nobody dances, so read the vote as gratitude. Find out which song gets them up and pass it to whoever is running the music.
Who is most likely to take the map on a scavenger hunt and lead the team straight to the answer?
Why ask it
If a hunt is on today's schedule, the vote has just picked a navigator. Otherwise ask about the last time their sense of direction saved a group.
Who is most likely to crack the escape room with one sudden idea?
Why ask it
Lists, hunches or trying every key in every lock: which is their method? A teammate can often add a moment from a real project when the same thing happened at a whiteboard.
Who is most likely to take a friendly game of mini golf more seriously than anyone expected?
Why ask it
A competitive streak is funny when the prize is a plastic trophy, and the person who has one generally knows it. They may state their rules of fair play for the record, and are owed a rematch.
Who is most likely to give a two-minute speech at the team dinner that people quote on Monday?
Why ask it
Do not put them on the spot unless they offer. Asking for only the opening line gives them the laugh without the pressure of a full speech.
Who is most likely to organize the group photo and get every single person into the frame?
Why ask it
Take the photo now, with the person named directing. It will be the one picture from the day with nobody missing, which is exactly the talent being voted on.
Who is most likely to sign up for karaoke first and bring three colleagues along?
Why ask it
Signing up is only half of it: the recruiting is what gets an evening going. Which song, and which three colleagues? The three are free to decline.
Who is most likely to have a whole table laughing within five minutes of sitting down?
Why ask it
Whoever writes the seating plan should take down this name. People who shared a table with them today can confirm the result, and say what the first laugh was about.
Who is most likely to build the tallest tower in the spaghetti and marshmallow challenge?
Why ask it
Votes tend to split between the planner and the person who just starts building. Ask each nominee for their approach in one sentence, then run the challenge if supplies allow.
Who is most likely to know the rules of every board game on the table and explain them in under a minute?
Why ask it
Time them on a game the group only half knows. A quick explainer is the reason a game starts while people still want to play it, so seat this person in the middle of the table.
Who is most likely to sit with a different department at lunch and know everyone by dessert?
Why ask it
Who did they meet today, and what is one thing they learned? Asked before the next meal, it works as a nudge for everybody else to change seats.
Who is most likely to plan the snacks and the playlist for the bus ride?
Why ask it
To this person the ride there counts as part of the day. Put them in charge of the trip home and open the floor to requests, songs first and snacks second.
Who is most likely to suggest a volunteer day and get the whole team signed up?
Why ask it
Which cause would they choose, and what would the team spend the day doing? If the room likes the answer, someone should write down a date before the feeling fades.
Who is most likely to have a slideshow of the day's photos ready before the bus gets home?
Why ask it
Make the job official: they collect everyone's pictures from today. Say where to send them now, while phones are still in hands.
Who is most likely to cheer the loudest for the other team?
Why ask it
Sportsmanship deserves a prize of its own. Both teams give this person one cheer at full volume, so they find out what it is like on the receiving end.
Who is most likely to make sure the leftover catering goes home with someone who wants it?
Why ask it
Practical kindness, and nothing goes in the bin. Put them in charge of today's leftovers and let them hand out the boxes as they see fit.
How to run most likely to at work
Practical guidance for the conversation itself
Setting it up with a team
Say the rule before the first prompt
Tell the group that every prompt is a compliment or a harmless habit, that nobody is being voted worst at anything, and that anyone can pass on a prompt without explaining. A colleague deciding whether to join in wants to know the game is safe first, and hearing the rule out loud answers that.
Choose eight to twelve prompts in advance
Do not read the list from the top. Pick prompts that fit people you know will be there, mix the funny habits with two or three plain thank-yous from the teammates group, and make sure your selection could be won by at least six different people. Ten minutes is long enough for a meeting warm-up.
Vote all at once, and allow self-votes
In a room, everyone points on a count of three, which stops the team from waiting to see where the manager points. Let people vote for themselves too. A colleague who proudly claims the label maker has made the game easier for everyone else.
Do the thing in the note
Each prompt comes with a suggestion for what happens after the vote: a quick test, a story, a thank-you from the people who benefited. That half minute is the point of the game. Without it you are only announcing names, and the person named has nothing to do but smile.
Voting on a video call
Chat on a countdown
Read the prompt, give people a moment to type a name in the chat without pressing enter, then count down from three so the names arrive together. It works on any platform, takes no setup, and the wall of names is fun to read out.
A poll for bigger groups
Past about fifteen people the chat scrolls too fast to follow. Use the platform's poll tool with names as the options, or split into breakout rooms of five and let each room report one result. With a poll, show the winner and skip the percentages.
Give the winner the screen
On a call the named person can disappear into a grid of faces. Say their name, invite them to unmute, and let them hold something up, share a photo or answer the follow-up. Cameras stay optional: a voice or a typed reply counts.
When half the team is in one room
Run the vote in the chat for everyone, including the people sitting at the table. Otherwise the room points and laughs while the people on the screen watch a game they are not in.
Awards at an away day
Collect the votes beforehand
Send a short form a week ahead with ten to fifteen prompts and a dropdown of names. Nobody sees the counts, you get time to spot problems, and people who would never point at a colleague in public will happily fill in a form.
One award each
Go through the results before anything is printed. Where one person has won four prompts, give them the one that suits them best and pass the others to the runners-up. If the team is small enough, add prompts until every person has a certificate.
Write the reason on the certificate
The prompt becomes the award title: Most Likely to Know Where Everything Lives. Underneath, add one line from a colleague saying why. That line is what gets pinned up at a desk afterward.
Keep the ceremony short
Two awards a minute is a good pace: title, name, applause, and one sentence from the winner if they want it. Hand them out between courses or just before the day wraps up, when people are relaxed and everyone is still there.
How to stop it turning into a roast
Test every homemade prompt
Teams start inventing their own prompts within minutes, and that is where roasts begin. The test is simple: would the winner be happy to see it on a certificate at their desk? Looks, age, lateness, pay, who is good at their job, dating and drinking all fail it, however funny the room finds them.
Stop the pile-on early
One story about the winner is a tribute. A third person adding another example of the same habit is a pile-on. Cut in after the first story with the follow-up from the note, or go to a new prompt, and nobody will notice you did it on purpose.
When the manager is playing
A team may vote more carefully when the boss is watching, and a manager's own vote can sound like a performance review. A manager who joins in should point last or vote for themselves, and should be a good sport when they win the label maker.
Spread the wins around
Keep a rough count as you go. If one popular person keeps winning, choose prompts built for someone else, and if a quiet colleague has not been named, pick the sincere prompt you know belongs to them. Whoever runs the game is allowed to steer it.
If a vote stings anyway
You cannot predict every sore spot. When someone goes quiet after being named, resist the urge to defend the prompt or tell them how it was meant. Read the next one, make it a sincere one from the teammates group, and find the person at the break to ask whether that was all right.