“Would you rather” questions are a fantastic tool for team managers, remote teams, and event organizers looking to spark lively conversations and connect with colleagues on a more personal level.
With a blend of humor and curiosity, these questions can lighten the mood, break down barriers, and make team meetings something to look forward to.
In this article, we’ll dive into 101 of the best “would you rather” questions for work, designed to bring a smile to your face and strengthen your team’s bond.
Why Use “Would You Rather” Questions?
Breaking the Ice
Breaking the ice in a team setting can sometimes feel like a challenge, especially in virtual environments. This is where “would you rather” questions come in handy. They’re a simple yet effective way to ease tension and get everyone talking.
By posing light-hearted dilemmas, you create an environment where team members can express opinions without feeling pressured. These questions serve as conversation starters, encouraging participation from even the most reserved members.
Unlike formal introductions or standard icebreakers, “would you rather” questions can reveal a bit of personality, allowing colleagues to connect over shared interests or laugh over diverse choices.
Building Team Dynamics
Effective teams thrive on strong dynamics and mutual understanding. “Would you rather” questions help in building these dynamics by encouraging team members to interact in a relaxed and enjoyable manner.
When team members share their preferences and rationale behind their choices, it provides insight into their thinking processes and values.
This can be particularly useful for managers to understand their team better and tailor their approach accordingly.
Encouraging Creative Thinking
“Would you rather” questions aren’t just fun, they can also be a powerful tool to encourage creative thinking. These questions often present unusual scenarios that require out-of-the-box thinking.
When team members are asked to choose between two seemingly impossible options, they tap into their creativity to justify their choices.
This kind of mental exercise helps in developing problem-solving skills and can stimulate innovative ideas.
101 of the Best “Would You Rather” Questions for Work
Business Questions
- Would you rather lead a high-risk, high-reward project or a safe, steady one? 🚀
- Would you rather have unlimited PTO with a lower salary or limited PTO with a higher salary? 🌴💰
- Would you rather work with a demanding client who pays well or an easygoing client with a modest budget? 🤔
- Would you rather innovate a new product or optimise an existing one? 💡🔧
- Would you rather attend a week-long intensive training or spread it out over several months? 📅🏋️♂️
- Would you rather manage a small team with a tight-knit culture or a large team with diverse skills? 👥🌐
- Would you rather have a job you love with a long commute or a job you’re neutral about that’s ten minutes from home? 🚗❤️🏠
- Would you rather hit quarterly goals consistently or land one huge annual deal? 🎯🏆
- Would you rather work for a startup where you wear many hats or a large corporation with a clearly defined role? 🎩🏢
- Would you rather have a flexible schedule but work weekends or a strict 9-to-5 with free weekends? ⏰🕘
Personal Questions
- Would you rather be able to travel for free anywhere in the world, but never settle down, or have a permanent home, but never travel again? 🌍🏡
- Would you rather have an unlimited wardrobe but never be able to wear the same outfit twice, or a limited wardrobe with your absolute favourite pieces? 👗👖
- Would you rather be incredibly skilled at a hobby you love but can’t monetise, or moderately skilled and make a living from it? 🎨💵
- Would you rather always have to say everything on your mind, or never be able to speak again? 🤐🗣️
- Would you rather spend a month without any technology or a month without human interaction? 📵👥
- Would you rather have the ability to read minds but get headaches or be able to see into the future but experience constant dejá vu? 🧠🔮
- Would you rather explore space or the deepest parts of the ocean? 🚀🌊
- Would you rather have an endless summer or a permanent winter? 🌞❄️
- Would you rather be famous for doing something embarrassing or be forgotten entirely? 📸🤦♂️
- Would you rather have the power to change one law or the ability to establish a new tradition? ⚖️🎉
Fun Questions
- Would you rather have a pet unicorn or a pet dragon? 🦄🐉
- Would you rather always be 10 minutes late or always be 20 minutes early? ⏰🤔
- Would you rather live in a world made of candy or a world made of toys? 🍬🎲
- Would you rather have a pause button for life or a rewind button? ⏸️⏪
- Would you rather be able to control the weather or talk to animals? 🌦️🐾
- Would you rather have a flying carpet or a car that can go underwater? 🧞♂️🚗🌊
- Would you rather eat only pizza for a year or never eat pizza again? 🍕😱
- Would you rather attend Hogwarts or live in Narnia? 🧙♂️🦁
- Would you rather be able to teleport anywhere in the world or be able to time travel but only to the past? 🌍⏳
- Would you rather always have to sing karaoke every time you speak or dance every time you move? 🎤💃
Thought-provoking Questions
- Would you rather have the power to erase one past mistake or foresee a huge future decision? 🤔🔮
- Would you rather dedicate your life to solving one global issue or improve a local community drastically? 🌍🏡
- Would you rather be completely honest and risk hurting feelings or tell white lies to keep peace? 🤐🕊️
- Would you rather never be able to make a new friend or never be able to keep an old one? 🤝🚪
- Would you rather know the date of your death or the cause of it? 📅⚰️
- Would you rather experience a constant high of happiness or a continuous state of calm serenity? 😊🌿
- Would you rather live in a world where everyone ignores you or a world where everyone is your constant critic? 👥🔍
- Would you rather have the ability to change others’ opinions or your own? 🗣️🤔
- Would you rather discover a new planet or find a new cure for a disease? 🌌🧬
- Would you rather be remembered for your kindness or your intelligence? ❤️🧠
Motivational Questions
- Would you rather achieve a lifelong dream with no recognition or accomplish something unexpected with widespread acclaim? 🎯🏆
- Would you rather inspire one person profoundly or motivate a thousand people slightly? 💬💡
- Would you rather be known for your optimism during tough times or your practicality during crises? 😊🛠️
- Would you rather overcome a personal fear to achieve a goal or help someone else overcome theirs? 😰➡️💪
- Would you rather constantly learn new things or master one skill completely? 📚🎨
- Would you rather be a mentor to someone younger or seek guidance from someone more experienced? 👩🏫👨🏫
- Would you rather work towards a significant change in your field or steadily improve small aspects? 🔄🔧
- Would you rather find motivation from competition or collaboration? 🤝🏆
- Would you rather focus on personal achievements or team accomplishments? 🤔👥
- Would you rather chase your own success or contribute to someone else’s? 🌟🤝
Goal-related Questions
- Would you rather hit all your quarterly targets and receive a small bonus, or exceed one significant annual goal and get a large bonus? 💰
- Would you rather lead a project that transforms the company culture or one that boosts revenue by 20%? 🌟
- Would you rather work towards a promotion within a year or take on a challenging project for the experience and growth? 🚀
- Would you rather be recognised for your teamwork in achieving a goal, or receive individual accolades for your contribution? 🤝🏅
- Would you rather focus on short-term successes or build strategies for long-term sustainability? ⏳
- Would you rather work on a project with immediate financial impact or one with lasting social influence? 💼🌿
- Would you rather achieve a personal milestone your team isn’t aware of, or celebrate a team goal collectively? 🎉
- Would you rather mentor a junior team member to achieve their first big goal or attend a workshop to develop a new skill yourself? 👨🏫👩💼
- Would you rather finish a project ahead of schedule with satisfactory results, or take longer to ensure exceptional outcomes? ⏰✨
- Would you rather receive a personal thank you from the CEO for your success or get a public shout-out at a company meeting? 🎤🙌
Icebreaker Questions
- Would you rather have every meeting start with a joke or end with a team cheer? 😂👏
- Would you rather brainstorm new ideas during a fun team picnic or a cozy café meeting? 🧺☕
- Would you rather share an office with a colleague who loves music or one who loves silence? 🎵🤫
- Would you rather have an office with a view of the city skyline or a peaceful park? 🌆🌳
- Would you rather attend a work conference in a bustling city or a tranquil resort? 🏙️🏝️
- Would you rather have team-building activities in an escape room or during a cooking class? 🔍🍳
- Would you rather receive a personal handwritten note of appreciation or a public shout-out at a team meeting? ✍️🎉
- Would you rather have a team lunch at a new restaurant every month or have a monthly international food potluck? 🍽️🌎
- Would you rather work from a high-tech, futuristic office or a warm, vintage-inspired space? 🤖📚
- Would you rather have a coffee machine that never runs out or a snack drawer that’s always full? ☕🍫
Morale-boosting Questions
- Would you rather have a surprise team lunch catered by your favourite restaurant 🍽️ or an unexpected team outing to a fun activity? 🎳
- Would you rather start every team meeting with a funny meme or end with a motivational video? 😂📹
- Would you rather have a weekly “no-email day” or a “PJ day” where the dress code is comfort only? 📧🚫🛌
- Would you rather receive a personalised thank-you note from every team member 📝 or a group video shout-out for your efforts? 📽️
- Would you rather participate in a team karaoke night 🎤 or a team cook-off challenge? 🍳
- Would you rather have the team invent a fun secret handshake 🤝 or create a motivational team chant? 🗣️
- Would you rather share a fun fact about yourself at each meeting or have a “mystery fact” week where you guess whose fact it is? 🕵️♀️
- Would you rather have office nap pods available 😴 or an unlimited snack bar? 🍪
- Would you rather celebrate team success with a pizza party 🍕 or an ice cream social? 🍦
- Would you rather have a team appreciation day every quarter 🎈 or a small, personalised gift for each team member annually? 🎁
Remote-team Questions
- Would you rather have a full day of uninterrupted focus time or frequent but short breaks to chat with teammates? 🧘♂️💬
- Would you rather attend a virtual team meeting with a fun dress-up theme or a meeting with an open mic for impromptu karaoke? 🎩🎤
- Would you rather work from your dream vacation spot but with unstable internet or from home with perfect connectivity? 🏝️📶
- Would you rather have a weekly virtual coffee chat with one team member at a time or a monthly virtual happy hour with the whole team? ☕🍹
- Would you rather collaborate on a project via a shared virtual whiteboard or through a series of brainstorming calls? 🖥️📞
- Would you rather receive virtual shout-outs in a team chat or personalised emails of appreciation from your manager? 📣📧
- Would you rather have a team-building exercise that involves playing online games or solving a virtual escape room together? 🕹️🔍
- Would you rather attend a virtual conference full of engaging speakers or have access to a comprehensive e-learning platform? 🎤🎓
- Would you rather switch to a four-day workweek with longer hours or continue with a five-day workweek with standard hours? ⏰📆
- Would you rather have team meetings start with a quick mindfulness session or end with a motivational quote? 🧘♀️💬
NSFW Questions
- Would you rather accidentally hit “reply all” on an email containing your salary details or your browser history? 📧🕵️♂️
- Would you rather be caught singing your favourite guilty pleasure song loudly in the office or dancing awkwardly when you think no one’s watching? 🎤💃
- Would you rather have your personal phone hacked or accidentally share a questionable meme in the company group chat? 📱😳
- Would you rather face a wardrobe malfunction during an important video call or spill coffee on yourself in a meeting? 👔☕
- Would you rather have your office chair replaced with a bean bag or your desk replaced with a treadmill desk for a week? 🪑🏃♀️
- Would you rather send a love letter to a colleague by mistake or receive a romantic gift at work addressed to someone else? 💌🎁
- Would you rather have your embarrassing childhood photos shared during a team presentation or your karaoke video? 📸🎤
- Would you rather get a tattoo of the company logo visible during meetings or have a forgotten Zoom filter on? 🖋️😅
- Would you rather discuss your most awkward office moment with the CEO or lead a team-building activity you’re unprepared for? 🙈😬
- Would you rather confess to your work crush or have your manager accidentally find out about it via a misdirected email? 💌❤️
Bonus Question
Need to gather team feedback? Just aaask
aaask streamlines the process of collecting and managing team feedback.
With aaask, you can set up check-ins tailored to your team’s needs, ensuring everyone’s voice is heard.
Whether it’s daily updates, weekly reflections, or fun team-building questions, aaask helps you keep track of all feedback in one organised place.
Invite team members to participate in specific check-ins, creating a focused environment for feedback on relevant topics. And schedule reminders so everyone is prompted to answer, making sure you don’t have to personally chase people up.
Plus, with automatic summaries, you can quickly review insights and engage in meaningful discussions.
This centralised approach to feedback not only saves time but also enhances collaboration by fostering an open and inclusive feedback culture.
By using aaask, you empower your team to share their thoughts effortlessly, leading to actionable insights and stronger team dynamics. Visit aaask to start your 30-day free trial and experience a new way of engaging with your team.
