Starting a conversation at work does not always have to feel formal or serious. A few simple choices can help coworkers talk, laugh, and learn more about each other. This-or-that questions for work are an easy way to bring people together during breaks, team activities, office parties, or casual chats.
These questions give everyone two options, so there is no need to think of a long answer. Tea or coffee? Early start or late start? Emails or phone calls? Simple choices can lead to surprisingly fun conversations.
They can also work well for team-building activities. A quick round can help new employees feel more comfortable around their coworkers. Managers can use them during informal meetings, while teams can add them to office games or virtual gatherings.
Looking for something funny? There are plenty of playful choices. Want something more interesting? You can ask questions about work habits, communication styles, goals, routines, and personal preferences without getting too personal.
The best part is how easy these questions are to use. You can ask one during lunch, send a few in a group chat, or create a full game for your next team activity. Keep the questions light, let everyone choose an option, and allow the conversation to continue naturally.
From funny office choices to questions for managers, employees, coworkers, and teams, this list has plenty of ideas to try. Pick a few favorites and see where the conversation goes. Ready to get started? Here are some fun and easy choices for your next workplace conversation.
This or That Questions for Work
- Would you rather work from home or work in an office?
- Would you rather start work early or finish work late?
- Would you rather have a four-day workweek or shorter workdays?
- Would you rather have coffee or tea at work?
- Would you rather attend a meeting or send an email?
- Would you rather work alone or with a team?
- Would you rather have a quiet office or a lively office?
- Would you rather sit near a window or near the door?
- Would you rather have a morning meeting or an afternoon meeting?
- Would you rather use a laptop or a desktop computer?
- Would you rather have flexible hours or a fixed schedule?
- Would you rather take a long lunch or leave work early?
- Would you rather have music in the office or complete silence?
- Would you rather have a private office or a shared workspace?
- Would you rather work on one big project or several small projects?
- Would you rather give a presentation or write a report?
- Would you rather make phone calls or answer emails?
- Would you rather have a team lunch or a team game?
- Would you rather work with a strict deadline or a flexible deadline?
- Would you rather have fewer meetings or fewer emails?
- Would you rather work in the morning or at night?
- Would you rather have a standing desk or a regular desk?
- Would you rather take notes by hand or type them?
- Would you rather work on creative tasks or practical tasks?
- Would you rather plan everything or work as things happen?
- Would you rather have a big office or a small office?
- Would you rather lead a project or support a project?
- Would you rather receive feedback privately or during a team meeting?
- Would you rather have a busy day or a quiet day?
- Would you rather work with numbers or words?
- Would you rather have snacks at your desk or a snack room?
- Would you rather attend a workshop or watch a training video?
- Would you rather have a casual dress code or a formal dress code?
- Would you rather have a company lunch or a company dinner?
- Would you rather finish one task before starting another or multitask?
- Would you rather have a whiteboard or a digital planning board?
- Would you rather have daily check-ins or weekly check-ins?
- Would you rather work on a new project or improve an old one?
- Would you rather receive praise in person or by email?
- Would you rather have a short meeting or a detailed meeting?
- Would you rather solve a problem alone or ask for help?
- Would you rather have a busy inbox or a busy calendar?
- Would you rather work in a large company or a small company?
- Would you rather have a desk phone or use your mobile?
- Would you rather attend an office party or a team outing?
- Would you rather have a flexible lunch break or a flexible start time?
- Would you rather organize an event or attend one?
- Would you rather work on something familiar or learn something new?
- Would you rather have a personal assistant or better office equipment?
- Would you rather end Friday early or start Monday late?
Funny This or That Questions for Work
- Would you rather attend five meetings in one day or answer 100 emails?
- Would you rather forget your password or forget your meeting time?
- Would you rather have your computer freeze during a presentation or your microphone stop working?
- Would you rather accidentally reply to everyone or send an email without an attachment?
- Would you rather work beside a loud talker or a constant snack eater?
- Would you rather spill coffee on your desk or drop your lunch?
- Would you rather wear the same outfit for a week or have mismatched shoes for a day?
- Would you rather have a funny ringtone during a meeting or a loud notification?
- Would you rather call your manager by the wrong name or send them the wrong file?
- Would you rather have your chair squeak all day or your keyboard make loud sounds?
- Would you rather join a meeting five minutes late or five minutes too early?
- Would you rather have a printer that jams every day or a mouse that stops working?
- Would you rather accidentally share your screen or forget to mute yourself?
- Would you rather work with a very talkative coworker or a very quiet coworker?
- Would you rather have a desk covered in papers or sticky notes?
Interesting This or That Questions for Work
- Would you rather learn a new skill or improve an existing skill?
- Would you rather work in another country or another city?
- Would you rather manage a large team or a small team?
- Would you rather create a new product or improve an existing one?
- Would you rather work four days a week or six hours every day?
- Would you rather attend an industry event or an online workshop?
- Would you rather have more responsibility or more free time?
- Would you rather become an expert in one area or learn several areas?
- Would you rather work on a creative project or a research project?
- Would you rather have a mentor or become a mentor?
- Would you rather change your job role or change your work schedule?
- Would you rather travel for work or work entirely from home?
- Would you rather lead a presentation or host a discussion?
- Would you rather solve a difficult problem or create a new idea?
- Would you rather have more vacation days or a shorter workweek?
This or That Questions for Coworkers
- Would you rather have lunch together or grab coffee together?
- Would you rather sit together or work in separate spaces?
- Would you rather chat in person or message online?
- Would you rather share snacks or share office stories?
- Would you rather work on the same project or different projects?
- Would you rather have a team lunch or a coffee break?
- Would you rather help with a presentation or help with a report?
- Would you rather attend a workshop together or a company event?
- Would you rather discuss work or weekend plans?
- Would you rather have a quick chat or a long conversation?
- Would you rather share a desk area or share a meeting room?
- Would you rather work together in the morning or afternoon?
- Would you rather exchange book recommendations or movie recommendations?
- Would you rather play an office game or take a group break?
- Would you rather have lunch inside or outside the office?
This or That Questions for Colleagues
- Would you rather send an email or make a quick call?
- Would you rather have a short meeting or a long meeting?
- Would you rather work on a shared document or separate files?
- Would you rather discuss ideas in person or online?
- Would you rather have a weekly meeting or a daily check-in?
- Would you rather share tasks or handle them separately?
- Would you rather receive a message or receive an email?
- Would you rather work on a deadline together or separately?
- Would you rather plan ahead or decide as you go?
- Would you rather have lunch together or take separate breaks?
- Would you rather exchange tips or share resources?
- Would you rather discuss ideas over coffee or during a meeting?
- Would you rather review work together or independently?
- Would you rather attend training together or watch it separately?
- Would you rather solve a problem together or compare solutions afterward?
This or That Questions for Teams
- Would your team rather have a team lunch or team breakfast?
- Would your team rather work in person or remotely?
- Would your team rather have one long meeting or several short meetings?
- Would your team rather play a quiz or a guessing game?
- Would your team rather have a casual Friday or a themed day?
- Would your team rather celebrate birthdays or project milestones?
- Would your team rather have a team outing or an office party?
- Would your team rather work on one large project or several smaller ones?
- Would your team rather use chat or email?
- Would your team rather have a shared calendar or a shared task list?
- Would your team rather brainstorm in person or online?
- Would your team rather have weekly goals or monthly goals?
- Would your team rather have flexible hours or flexible locations?
- Would your team rather attend a workshop or a team activity?
- Would your team rather start with a quick meeting or a quick game?
This or That Questions for Employees
- Would you rather have flexible hours or more vacation days?
- Would you rather work from home or from the office?
- Would you rather receive a bonus or extra vacation time?
- Would you rather have a shorter workday or a shorter workweek?
- Would you rather have more training or more project opportunities?
- Would you rather work on a new task or a familiar task?
- Would you rather receive written feedback or verbal feedback?
- Would you rather have a quiet workspace or a social workspace?
- Would you rather choose your own schedule or your own projects?
- Would you rather attend a conference or a professional course?
- Would you rather have a personal workspace or a shared workspace?
- Would you rather have more team activities or fewer meetings?
- Would you rather learn from a manager or a coworker?
- Would you rather take a long lunch or finish early?
- Would you rather have a four-day week or longer holidays?
This or That Questions for Managers
- Would you rather lead a small team or a large team?
- Would you rather have daily updates or weekly updates?
- Would you rather give feedback in person or by email?
- Would you rather manage one large project or several small projects?
- Would you rather hire someone experienced or someone eager to learn?
- Would you rather have a team meeting or individual check-ins?
- Would you rather set detailed plans or broad goals?
- Would you rather solve a problem yourself or guide your team through it?
- Would you rather have flexible schedules or fixed schedules?
- Would you rather organize a team lunch or a team activity?
- Would you rather focus on deadlines or long-term plans?
- Would you rather have a creative team or a highly organized team?
- Would you rather work with written reports or quick updates?
- Would you rather train new employees or mentor experienced employees?
- Would you rather start the week with planning or finish the week with a review?
Conclusion
This or that questions for work can make everyday conversations more enjoyable and help people connect at the office. From funny choices to thoughtful workplace topics, there are plenty of options for coworkers, teams, employees, and managers. Pick a few questions for your next break, meeting, or team activity and let everyone share their choices.
