100 winter would you rather questions for work
Winter would you rather questions give your team two cold-weather choices and everyone picks a side. Here are 100 clean ones for December through February, with no holiday needed. Tap the picker to put one on a shared screen.
Snow and coldWould you rather get one huge snowstorm a year or a light dusting every week all winter?
How to play winter would you rather
Read one question, everyone votes at once, and one person from each side gets 15 seconds to defend their pick. Eight to ten questions fill a 10-minute icebreaker; a meeting opener takes three or four. Every question is about the season, not a holiday, and all of them are safe to ask coworkers.
15 snow day would you rather questions
Cold-weather choices everyone can picture, even the teammates who have never shoveled a driveway.
1. Would you rather get one huge snowstorm a year or a light dusting every week all winter?
2. Would you rather have a heated driveway or heated seats in every car you ever ride in?
3. Would you rather build the biggest snow fort on the block or read by a frosty window all day?
4. Would you rather live somewhere with real winters or somewhere it never drops below 60 degrees?
5. Would you rather scrape ice off a windshield every morning or wait 15 minutes for a bus in the cold?
6. Would you rather wake up to a silent snowfall or fall asleep to sleet tapping on the window?
7. Would you rather go winter camping in a heated tent or spend one night in an ice hotel?
8. Would you rather see the northern lights once or a frozen waterfall every winter?
9. Would you rather have a coat that is always the right temperature or boots that never get wet?
10. Would you rather have a dog that lives for snow or a cat that refuses to go outside until April?
11. Would you rather shovel your own walk or secretly shovel your neighbor's walk before they wake up?
12. Would you rather have snow only on weekends or only on weekdays?
13. Would you rather sled down the biggest hill in town or ride a snowmobile across a frozen lake?
14. Would you rather walk on fresh snow that crunches or glide across a frozen pond?
15. Would you rather have one snowed-in week at home or one snowed-in weekend at a mountain lodge?
Want a host to run a winter game for your team?
Ten questions warm up a meeting. A live host runs the whole hour: winter games and trivia in small teams that change every round, scoring and music, with nothing for you to prep. It keeps a remote team of 15 or a 150-person kickoff on one Zoom call moving. Hosted games book about 2 weeks ahead; the hot chocolate kit workshop ships to every guest and books about 3 weeks ahead for US addresses.
Winter Fun & GamesStarting at $35 USD / person
Winter Showdown!Starting at $35 USD / person
Winter Resort Vacate-tion!Starting at $35 USD / person
Hot Chocolate BombStarting at $90 USD / person
Reserve online with a 50% deposit, or send your date and headcount for a full plan within 24 hours. More options on our virtual winter games page.
15 cozy would you rather questions for winter nights
Blankets, books and long evenings. A calm set for a small team or the end of a long week.
16. Would you rather have a fireplace in your bedroom or a hot tub on your back deck?
17. Would you rather spend a winter weekend in a cabin with no wifi or a city hotel with a heated rooftop pool?
18. Would you rather wear slippers to work all winter or a blanket cape to every meeting?
19. Would you rather finish one long novel this winter or ten short mysteries?
20. Would you rather learn to knit a scarf or learn to bake bread this winter?
21. Would you rather have soup night every Monday or a pancake breakfast every Sunday?
22. Would you rather binge a whole series in one snowy weekend or watch one episode a night until spring?
23. Would you rather nap in a sunny window seat or on a couch under three blankets?
24. Would you rather host a winter game night or a soup swap with friends?
25. Would you rather have a reading nook with a big window or a craft table stocked with every supply?
26. Would you rather have your home always smell like a wood fire or like fresh bread?
27. Would you rather hibernate for one week in January or get an extra hour of daylight every day?
28. Would you rather wear pajamas all weekend or get dressed up for a winter dinner out?
29. Would you rather fall asleep to rain on the roof or to the quiet of falling snow?
30. Would you rather sleep under flannel sheets or under a giant down comforter?
Want everyone holding a real mug while they answer? A hot chocolate bomb workshop ships the chocolate, sprinkles and marshmallows to every guest, and a host walks the team through making them live. Book about 3 weeks ahead for US addresses; each guest needs a microwave or stovetop and a fridge.
15 winter food would you rather questions
Comfort food and warm mugs. Easy for a lunch-and-learn or the first meeting back in January.
31. Would you rather have a hot cocoa bar at every meeting or a soup bar at every lunch?
32. Would you rather drink only hot drinks until March or only cold drinks all winter?
33. Would you rather have grilled cheese and tomato soup every Friday or ramen every Tuesday?
34. Would you rather make one big pot of stew that lasts all week or a new dinner every night?
35. Would you rather have fresh cinnamon rolls every morning or a hot pretzel every afternoon?
36. Would you rather own a waffle maker that never sticks or a slow cooker that never burns?
37. Would you rather have hot cocoa that never cools down or toast that always comes out golden?
38. Would you rather dip everything in chocolate fondue or in cheese fondue?
39. Would you rather put maple syrup on everything or honey on everything?
40. Would you rather taste every stall at a winter food festival or cook one perfect dish at home?
41. Would you rather eat oatmeal with ten toppings or eggs any style every winter morning?
42. Would you rather make s'mores over a fire pit or bake cookies in a warm kitchen?
43. Would you rather have a lunch box that keeps soup hot until 3 p.m. or a mug that keeps tea hot all day?
44. Would you rather judge the office chili cook-off or enter it?
45. Would you rather get a tea of the month or a coffee of the month all winter?
15 funny winter would you rather questions
Snowmen, penguins and slightly cursed weather. Both sides are ridiculous, so nobody's pick is wrong.
46. Would you rather have every snowflake that lands on you ring like a tiny bell or every step in snow squeak like a toy?
47. Would you rather be a penguin who can't swim or a polar bear who hates the cold?
48. Would you rather have a snowman that follows you around or a snowball that never melts in your pocket?
49. Would you rather wear a full snowsuit to every video call or join every call from inside a blanket fort?
50. Would you rather have your breath freeze into little letters or your words come out as visible snowflakes?
51. Would you rather have a car that warms up instantly but only plays polka or one that takes 20 minutes but plays your favorites?
52. Would you rather live in a snow globe someone shakes once a day or an igloo with excellent wifi?
53. Would you rather have a pet snowman who lives in your freezer or a pet penguin who lives in your bathtub?
54. Would you rather wear mittens on your hands all winter or earmuffs that only play the weather report?
55. Would you rather have every icicle play a note when touched or every snowbank thump like a drum when kicked?
56. Would you rather have a sled that only goes uphill or skis that only go backward?
57. Would you rather have hot cocoa come out of the office water fountain or snow fall only in the break room?
58. Would you rather have a weather app that only speaks in riddles or a groundhog who texts you the forecast?
59. Would you rather wear four layers everywhere or carry a tiny space heater in your bag?
60. Would you rather have a snowball fight where everyone has perfect aim or where nobody can hit anything?
Want more silly ones for the rest of the year? Our funny would you rather questions have 150 more. For a full hour of laughs, Comfy Cozy Game Shows is a hosted game show you can book with its winter theme, which leaves the holidays out.
15 winter would you rather questions for work
For the January kickoff, a Monday meeting or the long stretch to spring. About ten of these fill a 10-minute opener.
61. Would you rather have a walking meeting in the snow or a meeting in front of a fireplace video?
62. Would you rather start work an hour later all winter or finish an hour earlier while it's still light out?
63. Would you rather work from a ski lodge for a week or from a beach cafe for a week?
64. Would you rather have a snow day that's fully off or one with a cozy half day of remote work?
65. Would you rather set one big goal for the new year or twelve small monthly ones?
66. Would you rather have a team soup potluck or a team hot chocolate tasting?
67. Would you rather keep a cozy blanket at your desk or a desk heater with three settings?
68. Would you rather run the first meeting of the year or get the recap in two lines?
69. Would you rather have the team's winter outing be tubing down a snowy hill or bowling in a warm alley?
70. Would you rather join winter calls with a cozy cabin background or a sunny beach background?
71. Would you rather start Mondays with warm drinks delivered or end Fridays with a team game?
72. Would you rather take a long weekend in January or a long weekend in February?
73. Would you rather have the office thermostat set exactly right or a free warm lunch every Thursday?
74. Would you rather clean out your inbox in January or your desk drawers?
75. Would you rather plan the winter team outing or plan the summer one?
Planning a January kickoff for 50 or more people? Chat votes get slow at that size, and a host-run game from our virtual winter games splits everyone into small teams so each person still gets a turn. Our kickoff meeting ideas cover the rest of the agenda.
How to run it in the office, hybrid or on Zoom
Four steps turn a list into a game. They work the same in a room or on a call.
- Choose a set for the mood. Funny or snow days to wake up a Monday, cozy or work for a calmer check-in. Put the question on screen or read it once.
- Vote with your hands, not your voice. Left hand for the first option, right hand for the second, all at once. On video, hold the hand up to the camera.
- Hear the strongest case from each side. One person per side, 15 seconds. Then re-vote; anyone who switched explains what won them over.
- Keep it to ten minutes. Eight to ten questions fill it. For a January kickoff opener, three or four is plenty.
- In the office: one side of the room per option, and the side with fewer people picks the next question.
- Hybrid: everyone votes in the meeting chat or a quick poll, people in the room too, so remote teammates count the same. Call on a remote person first.
- On Zoom, Teams or Google Meet: share the picker above, vote with reactions and unmute one defender per side.
- In a team chat channel: post one question each Monday morning in January with two emoji to vote, and share the closest split on Friday.
12 winter travel and sports would you rather questions
Mountains, beaches and the occasional curling stone. Good for teams that like to talk about trips.
76. Would you rather learn to snowboard or learn to cross-country ski this winter?
77. Would you rather spend a week in a snowy mountain town or a week on a warm beach?
78. Would you rather have front-row seats to a figure skating final or a curling final?
79. Would you rather try curling for the first time or try ice climbing?
80. Would you rather ride on a dog sled or in a horse-drawn sleigh?
81. Would you rather visit a winter festival full of ice sculptures or a hot spring surrounded by snow?
82. Would you rather fly somewhere warm the day after the first snow or stay home for the coziest week of the year?
83. Would you rather have a lift ticket for every mountain in the country or a free week at one favorite resort?
84. Would you rather go ice fishing for a day or snowshoe up a mountain?
85. Would you rather watch a hockey game from right against the glass or a ski jump from the bottom of the hill?
86. Would you rather take a train through snowy mountains or a road trip through them?
87. Would you rather spend a winter evening at an outdoor ice rink or an indoor climbing gym?
Team loves an adventure? Winter Resort Vacate-tion is a hosted escape game set at a snowy mountain resort, with puzzles and silly contests in small teams on Zoom.
13 rapid fire winter would you rather questions
Short enough to read in two seconds. Fire five in a row in the chat and skip the debate.
88. Would you rather have snow or sunshine all January?
89. Would you rather wear a beanie or a hood?
90. Would you rather go sledding or snowshoeing?
91. Would you rather have tea or cocoa?
92. Would you rather drink from a mug or a thermos?
93. Would you rather watch the snow fall or play in it?
94. Would you rather make snow ice cream or a snow sculpture?
95. Would you rather have January or February?
96. Would you rather have a cabin in the woods or a loft in the city?
97. Would you rather wake before sunrise or sleep past it?
98. Would you rather play cards or a board game?
99. Would you rather shovel snow or use a snowblower?
100. Would you rather walk on ice or wade through slush?
Need a different format? Our winter this or that list is the two-word version, the winter icebreaker questions open up longer answers, and winter trivia makes a good second round. For the first weeks back, try these January icebreakers, and in February switch to Valentine's Day would you rather.
