Spark Conversations, Boost Team Chemistry, or Just Survive the Workday!
Stuck in a work rut? Need to break the ice, lighten a meeting, or just avoid awkward silence? These 99 brutally simple “Would You Rather” questions cut through small talk and force real choices. No fluff. No clichés. Just quick, punchy dilemmas that:
- Reveal quirks
- Test priorities
- Expose pet peeves
Why Scroll Away?
Every question below takes 5 seconds to read but could spark hours of debate, laughter, or unexpected honesty. Don’t just skim—challenge your team (or yourself) to answer all 99. You’ll either bond, vent, or finally figure out who’s actually stealing the office snacks. For even crazier choices, check out our Weird Would You Rather Questions and take the game to the next level!
❔99 Would You Rather Questions Especially for Work
Office Environment
❔1. 🌡️🆚🪟 Would you rather work in a windowless room with perfect temperature or a room with windows but broken HVAC?
❔2. 🪑🆚🗄️ Would you rather have a squeaky office chair or a wobbly desk?
❔3. 🥪🆚🚫 Would you rather share a refrigerator with messy coworkers or lose fridge access entirely?
❔4. 💡🆚🕯️ Would you rather work in a fluorescent-lit room or a dimly lit room with desk lamps?
❔5. 🛑🆚☕ Would you rather have a broken elevator or a broken coffee machine?
❔6. 🧼🆚🚽 Would you rather clean the office microwave weekly or clean the office bathroom monthly?
❔7. ❄️🆚🔥 Would you rather work in a room with no air conditioning or no heating?
❔8. 📠🆚🚪 Would you rather have a noisy printer nearby or a loud hallway outside your workspace?
❔9.👐🆚📦 Would you rather work in an open office with no privacy or a cubicle with no natural light?
Work Style
❔10. 📄🆚🎤 Would you rather write a 10-page report or give a 10-minute presentation?
❔11. 🧩🆚🧠 Would you rather tackle five easy tasks or one complex task daily?
❔12. 🧍🆚👥 Would you rather work alone with no feedback or collaborate with constant input?
❔13. ⏳🆚🌀 Would you rather finish work early with strict deadlines or take flexible time with no deadlines?
❔14. ✍️🆚💻 Would you rather take notes by hand or type them digitally forever?
❔15. 📅🆚🎲 Would you rather have a rigid daily schedule or a completely unpredictable workflow?
❔16. 📧🆚🗣️ Would you rather receive instructions via email or face-to-face?
❔17. 🔍🆚🖋️ Would you rather proofread a document or create one from scratch?
❔18. 📊🆚⚡ Would you rather plan a project for a week or execute it in a day?
Career Development
❔19. 🆙🆚💵 Would you rather get promoted without a raise or a raise without a promotion?
❔20. 🎲🆚🏆 Would you rather lead a high-risk project or assist on a guaranteed-success project?
❔21. 🤝🆚📚 Would you rather attend a networking event or a skills-training workshop?
❔22. 🎉🆚💰 Would you rather receive public praise or a private bonus?
❔23. 🏢🆚🚀 Would you rather work for a famous company with low pay or a startup with high pay?
❔24. 👹🆚😇 Would you rather have a mentor who’s harsh but helpful or one who’s kind but unskilled?
❔25. 🎤🆚📰 Would you rather present at a conference or write an industry article?
❔26. 🎯🆚🌈 Would you rather gain expertise in one skill or basic knowledge in five skills?
❔27. 🌅🆚🌇 Would you rather retire early with a modest pension or retire late with a large pension?
Team Dynamics
❔28. ⏰🆚👀 Would you rather work with someone who’s always late or someone who micromanages?
❔29. 🛠️🆚📋 Would you rather resolve a team conflict alone or involve HR immediately?
❔30. 🍱🆚🍻 Would you rather have a team lunch or a team happy hour?
❔31. 👫🆚👤 Would you rather collaborate with a close friend or a stranger?
❔32. 😠🆚👔 Would you rather receive harsh feedback from a peer or a manager?
❔33. 🌱🆚🛋️ Would you rather work with someone inexperienced but eager or skilled but lazy?
❔34. 💡🆚🚫 Would you rather do a group brainstorm alone or skip it entirely?
❔35. 🌟🆚👥 Would you rather take credit for a team success or let the team take credit?
❔36. 🧑🏫🆚📦 Would you rather train a new hire for a week or cover their workload for a month?
Work Challenges
❔37. 🔧🆚🙏 Would you rather fix a critical error before a deadline or apologize to a client afterward?
❔38. ⏳🆚📅 Would you rather work overtime for a week or work weekends for a month?
❔39. 🌐🆚📞 Would you rather lose internet access for a day or lose phone access for a week?
❔40. 😡🆚😴 Would you rather present to a hostile audience or a disinterested audience?
❔41. 👤🆚👔 Would you rather handle an angry customer or an angry executive?
❔42. 🕒🆚📤 Would you rather miss a deadline by an hour or submit incomplete work on time?
❔43. 🛠️🆚⏳ Would you rather troubleshoot a tech issue yourself or wait hours for IT support?
❔44. 📀🆚🧪 Would you rather work with outdated software or untested new tools?
❔45. 🔄🆚😬 Would you rather redo a month’s work or admit a mistake to your boss?
Work-Life Balance
❔46. ⏳🆚📅 Would you rather work four 10-hour days or five 8-hour days?
❔47. 📧🆚🌙 Would you rather answer emails on vacation or work late every day for a week?
❔48. 🥪🆚🚪 Would you rather skip lunch breaks for early departure or take lunch but leave late?
❔49. ∞🆚📆 Would you rather have unlimited paid time off with strict quotas or limited PTO with flexibility?
❔50. 🚌🆚🏠 Would you rather commute two hours daily or live near work with a smaller home?
❔51. 💰🆚🎉 Would you rather work holidays for double pay or have holidays off with no pay?
❔52. 🏕️🆚🌃 Would you rather attend a work retreat weekend or work overtime the following week?
❔53. 💸🆚🏢 Would you rather take a pay cut for remote work or keep your salary for in-office work?
❔54. 😴🆚🌅 Would you rather lose sleep to finish work or wake up early to complete it?
Technology & Tools
❔55. 🐢🆚🌐 Would you rather use a slow computer or a slow internet connection?
❔56. 📱🆚💻 Would you rather lose your work phone or your work laptop?
❔57. 📊🆚📽️ Would you rather use only spreadsheets for a month or only slideshows for a month?
❔58. ⌨️🆚🖱️ Would you rather have a keyboard with missing keys or a mouse that double-clicks?
❔59. 🍎🆚💻 Would you rather switch to a Mac if you’re a PC user, or vice versa?
❔60. 🗣️🆚☝️ Would you rather use voice commands for all typing or type with one finger forever?
❔61. 📺🆚🌀 Would you rather have a monitor that flickers or a fan that rattles?
❔62. 📼🆚🐞 Would you rather use software from 2005 or beta-test buggy new software?
❔63. 💾🆚🎲 Would you rather back up data manually daily or risk losing files automatically?
Workplace Ethics
❔64. 🚨🆚☮️ Would you rather report a coworker’s dishonesty or ignore it to keep team peace?
❔65. 🛡️🆚⚖️ Would you rather take blame for a team error or let the team face consequences?
❔66. 💰🆚🤝 Would you rather work for a company with unethical practices or earn less at an ethical company?
❔67. ✂️🆚📏 Would you rather meet quotas by cutting corners or miss quotas with proper methods?
❔68. 🤐🆚📢 Would you rather keep a client’s harmful secret or expose it and lose their business?
❔69. 🤑🆚🙅 Would you rather receive an undeserved bonus or decline it and explain why?
❔70. 🎭🆚🎯 Would you rather fake enthusiasm for a project or voice your concerns openly?
❔71. 📜🆚🎨 Would you rather follow an outdated policy or improvise without approval?
❔72. 🎓🆚👨👧 Would you rather hire an overqualified candidate or an underqualified referral?
Leadership & Management
❔73. 🌀🆚👔 Would you rather manage a disorganized team or report to a disorganized boss?
❔74. 🔥🆚🔄 Would you rather fire a underperforming employee or retrain them repeatedly?
❔75. 🚀🆚😴 Would you rather set ambitious goals that stress the team or easy goals that bore them?
❔76. 💡🆚🤖 Would you rather hire someone who challenges your ideas or agrees with everything?
❔77. 🦸🆚🤲 Would you rather lead a team through a crisis alone or delegate authority to others?
❔78. 🤝🆚🌟 Would you rather promote a loyal employee or a talented outsider?
❔79. 🗣️🆚🌸 Would you rather share negative feedback candidly or soften it to avoid conflict?
❔80. 📉🆚🔍 Would you rather take responsibility for a failed project or analyze its causes publicly?
❔81. 🎓🆚👔 Would you rather invest in employee training or hire already-trained staff?
Remote Work
❔82. 📹🆚🏢 Would you rather work remotely with daily video check-ins or work onsite with no oversight?
❔83. 📹🆚📧 Would you rather have Zoom meetings all day or reply to 100 emails daily?
❔84. 💡🆚📹 Would you rather lose power during a remote workday or lose video in a critical meeting?
❔85. 🛌🆚👔 Would you rather work in pajamas with camera off or dress professionally with camera on?
❔86. 🐶🆚👶 Would you rather have a pet interrupt meetings or a child interrupt meetings?
❔87. 🐢🆚🗣️ Would you rather use a slow VPN or a chatty coworker in your home workspace?
❔88. 🌍🆚🤝 Would you rather work in a different time zone than your team or your clients?
❔89. 📶🆚💻 Would you rather have your WiFi crash hourly or your work laptop crash daily?
❔90. 🖥️🆚🚗 Would you rather attend a virtual team-building activity or an in-person mandatory meeting?
Bonus Questions
❔91. 🗣️🆚🤫 Would you rather work with a talkative colleague or one who never speaks?
❔92. 🙊🆚📝 Would you rather have a boss who forgets your name or one who remembers every mistake?
❔93. 🤫🆚🎵 Would you rather work in silence or with non-stop background music?
❔94. 👔🆚👕 Would you rather wear a formal uniform daily or casual clothes with strict dress code rules?
❔95. ⏳🆚🕔 Would you rather have a 1-hour daily meeting or a 5-hour weekly meeting?
❔96. 🎁🆚📅 Would you rather receive a surprise performance review or a scheduled one?
❔97. 😴🆚😰 Would you rather work in a job that bores you or stresses you?
❔98. 💸🆚🎲 Would you rather take a pay cut to keep your job or risk layoffs for full salary?
❔99. 🔄🆚👋 Would you rather retire from your current job or switch careers every 5 years?
