Why the habit dies
It's almost never the questions. It's that one person becomes responsible for producing a good one before 9am, every single day, forever. That person gets busy, misses a Tuesday, feels a bit sheepish on the Wednesday, and by Friday nobody mentions it again. Three failure modes cover nearly all of it:
- The unpaid second job. Thinking of a fresh question daily is a real task that appears on nobody's list and gets no credit. It is the first thing dropped in a busy week.
- The same six voices. If answering means speaking up in a meeting, you hear from the same confident handful and everyone else waits it out. That's not engagement, that's an audience.
- Questions that cost something to answer. "What's your biggest fear?" and "What's your proudest moment?" ask for disclosure at work, to colleagues, on a Tuesday. People deflect, and the deflecting is what makes it feel cringe.
The fix for all three is the same shape: make the question arrive by itself, make answering a single tap rather than a performance, and keep the stakes at pineapple-on-pizza level. Nobody has ever felt exposed by admitting they're a thick-spread Vegemite person.
Would you rather questions
Safe anywhere — new starters, mixed seniority, clients in the room
- Would you rather sneeze glitter or hiccup bubbles?
- Would you rather live in outer space or under the sea?
- Would you rather have a laugh that sounds like a car horn or a goat?
- Would you rather have a pet dinosaur the size of a cat, or a pet cat the size of a dinosaur?
- Would you rather be chased by one horse-sized duck or a hundred duck-sized horses?
- Would you rather taste colours or see sounds?
- Would you rather live in a house made of biscuits or bubble wrap?
- Would you rather have a rewind button or a pause button for your day?
- Would you rather have a fridge that restocks itself or a washing basket that empties itself?
- Would you rather commute by zip line or pogo stick?
- Would you rather have a robot butler that judges you, or a parrot that repeats your thoughts?
- Would you rather be followed everywhere by a marching band or a completely silent mime?
- Would you rather have socks that always match or cables that never tangle?
- Would you rather always find your keys, or always find the end of the sticky tape?
- Would you rather have an office chair that spins forever, or a desk that lifts you to the ceiling?
- Would you rather your thoughts be narrated by a nature documentary host or a sports commentator?
- Would you rather have a tiny orchestra living in your bag or a tiny bakery in your desk drawer?
- Would you rather every photo of you be blurry or taken mid-blink?
- Would you rather wear flippers all day or oven mitts all day?
- Would you rather have a shower that sings back or a fridge that applauds your choices?
A bit bigger — good for a team that already talks
- Would you rather speak every language or play every instrument?
- Would you rather be the best in the world at something useless, or pretty good at everything?
- Would you rather visit the past for a day or the future for a day?
- Would you rather remember every dream you have or never dream again?
- Would you rather be able to talk to animals or make any plant grow instantly?
- Would you rather always be ten minutes early or never wait in a queue again?
- Would you rather be able to nap comfortably anywhere or never need a nap again?
- Would you rather know the time without a clock or always know which way is north?
- Would you rather live somewhere it never rains, or somewhere it rains gently every night?
- Would you rather have endless free ice cream or endless free flights?
Questions that start an argument
These are the ones worth saving for a flat Wednesday. They split a room roughly down the middle, and the split never lands where anyone expects. Two people will get genuinely heated about the straw. That's the point.
- Is a hot dog a sandwich?
- Does a straw have one hole or two?
- Is cereal a soup?
- Is water wet?
- Toilet roll: over or under?
- Milk first or cereal first?
- Does the week start on Monday or Sunday?
- Is the letter H said aitch or haitch?
- Is a tomato a fruit or a vegetable?
- Is a doughnut a cake or a bread?
- Is silence a sound?
- Is a hallway a room?
- Is an egg breakfast food or anytime food?
- Does pressing a lift button twice make it arrive faster?
- In a band name, is "The" part of the name?
- Do you say the alphabet or sing it?
- Is a chair with only one leg still a chair?
- If a turtle loses its shell, is it naked or homeless?
- Is a rubber duck a toy or a colleague?
- Is a piano a percussion instrument or a string instrument?
The Australian ones
Reliable in an Australian office, and unexpectedly good with a team split across states — the potato scallop question is a genuine map of the country.
- Is it a potato scallop or a potato cake?
- Vegemite on toast: thin scrape or thick spread?
- Is the ibis a bin chicken or a magnificent bird?
- Is a sausage roll a type of pie?
- Sauce on a meat pie: essential or optional?
- Hot chips: tomato sauce or gravy?
- Is a jaffle a toastie, or its own thing entirely?
- Tim Tam Slam: with tea or with hot chocolate?
- Fairy bread: sprinkles edge to edge or a bit sparse?
- Is the magpie warble the best bird sound going, or wildly overrated?
- Sand at the beach: half the fun, or a menace you find for weeks?
- Perfect Saturday: beach or bush?
- Which is the best bit of the week: Friday arvo or Saturday morning?
- Always find the good shopping trolley, or always find a park right out the front?
One-second preference questions
For a room that's tired, or a Monday. No thinking required, everyone already knows their answer, and the vote is over in twenty seconds.
- Tea or coffee?
- Cats or dogs?
- Pineapple on pizza?
- Crunchy or smooth peanut butter?
- Window seat or aisle seat?
- Sweet or savoury breakfast?
- Milk chocolate or dark chocolate?
- Books: paper or screen?
- Pancakes or waffles?
- Popcorn: sweet or salty?
- Pizza: thin crust or thick crust?
- Roller coaster: front seat or back seat?
- Weekend mornings: sleep in or up early?
- Fitted sheet: folded or rolled?
- Chocolate bar: break it into squares, or bite straight in?
- Lasagne: middle piece or corner piece?
- Always autumn or always spring?
- Long weekend: go somewhere, or stay home doing nothing?
What to avoid
A daily question is a low-stakes ritual, not a values exercise. The ones that go wrong nearly always ask for something a person can't take back:
- Anything that surfaces money, health, family status or religion. "Where are you really from", "when are you having kids", "what did you weigh" — even asked warmly, these land differently depending on who's in the room and who your manager is.
- Ranking colleagues. Who's funniest, who'd survive the apocalypse, who'd you pick first. Someone is always last.
- Anything that requires a story. "Most embarrassing moment" is a performance request, not a question, and it disproportionately costs the quietest person in the room.
- Anything that only lands for one group. A question about a TV show, a sport, or a school system splits the room into people who get it and people waiting for it to end.
The test is simple: could the newest person in the team answer it truthfully in one word, on their second day, in front of their manager? If not, save it.
How to run it so it lasts
- Take it off a human. The question should already be there when people arrive, not waiting on someone's Tuesday. That single change is the difference between a habit and a chore.
- One tap, not a round-the-room. A vote means everyone participates, including the people who'd never volunteer an answer out loud — and the split is more interesting than any one person's answer.
- Hide the tally until they've voted. Show a running score and people follow the crowd. The whole fun of "is a hot dog a sandwich" is finding out afterwards that the office is 60/40.
- Keep it to ninety seconds. The moment it needs an agenda item, it's finished.
- Let it be asynchronous. Post the link once. People tap it with their coffee, or at 9pm, or not at all. Nothing is scheduled and nobody is put on the spot.
Common questions
What is a good question of the day for work?
One that everyone can answer in a single word without revealing anything about themselves — a would-you-rather, a food argument, or a straight preference. "Is a hot dog a sandwich" works in every workplace. "What's your biggest regret" does not.
How do you run a daily question with a remote team?
Asynchronously, with a link rather than a meeting. Share one link that shows today's question and takes a tap to answer, then let people hit it whenever their day starts. Nobody has to be online at the same time, and people in other time zones aren't answering yesterday's question.
How long should a question of the day take?
Ninety seconds if it's in a stand-up, or no scheduled time at all if people answer it on their own. Once it needs its own agenda item it has stopped being a warm-up and started being a meeting.
Should you show the results before people vote?
No. Visible tallies pull people towards the leading answer, and the interesting part is the honest split. Hide the numbers until someone has picked a side, then show them what the room actually thinks.
What if someone doesn't want to answer?
Let them skip it, silently and without follow-up. A question of the day that tracks who hasn't participated has turned a bit of fun into attendance-taking, which is the fastest way to make people resent it.
Or let it run itself
That's what the tool below does: 160 questions in the bank, a new one every morning in your timezone, a live vote where the tally stays hidden until someone picks a side, and no repeats. You share one link with the team once and never think about it again. Free, no accounts, and you can add your own questions to the rotation.