Organizational Wellness

122 This or That Questions to Liven Up Work Meetings

Jul 20, 2023
Last Updated Jun 14, 2024

How do you get to know the people on your team? Sure, a lot of relationship-building happens organically over time. But you can always give it a helping hand with fun icebreaker activities or questions!

This or that questions can be an excellent icebreaker activity for work. They're simple to ask and don't take much time to play, so you can easily get through a few at the start of a meeting. Even better, they help your team get to know each other and understand how each other thinks. Team members who don't know each other well may be surprised to find they have lots in common, sparking great conversations.

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What Are This or That Questions?

This or that questions are a fun way to learn more about the people you work with. These types of questions are posed with two options, and the person you're asking must choose one of them. They can be used as an icebreaker, team-building activity, or even a conversation starter when you're getting lunch together! 

Whether you're asking about fun topics or sticking to work-related subjects, this or that questions can help you learn more about the people around you. They’re a simple way to get to know people a bit better by discovering their preferences out of two opposing options.

Working Style This or That Questions

You can use this or that questions as an informal way to understand how the people on your team like to work. If you ask questions about their preferred working styles, you can figure out what works best for your team. This can help you create a working environment that suits as many people on your team as possible, and can help everyone feel comfortable and productive when at work. This type of this or that question can also help team members work better together, as they better understand each others' working styles and preferences.

With that in mind, here are some example this or that questions to help you dig into how your team likes to work

  • Work in teams or work independently?
  • Structured workday or a flexible one? 
  • Find deadlines motivating or stressful?
  • Would you prefer a maker or manager schedule?
  • Strict routine or mix things up?
  • Work with music on or in silence?
  • Go into the office or work remotely?
  • Several short breaks or one long one?
  • Get in early or stay late?
  • Learn best by seeing or doing?
  • Meetings in person or on Zoom?
  • Save as you go or save at the end?
  • Open plan or cubicle?
  • Creative tasks or logical/analytical ones?
  • Meetings or emails?
  • Focused work or multi-tasking?

Office Life This or That Questions

Working in the office all day every day is no longer the norm. Only one in five U.S. workers go into the office every day, according to a 2022 report by Gallup, and around half work in a hybrid environment spending part of the week on-site and half at home. 

If you're an office-based company (or trying to tempt more people back into the office), it's important to create environments where employees feel comfortable, so they can focus on doing their best work. Use these questions to figure out what's most important to your teams when they're in the office. While these may feel like fun, informal icebreaker questions, they're a great way to gather insights for your office manager or HR team. 

Here are some this or that questions focused on work life in an office environment:

  1. Assigned desk or desk-hopping?
  2. Large meetings or small groups?
  3. Packed lunch or buy lunch?
  4. Dishwasher or coffee machine?
  5. Conference room meeting or desk meeting?
  6. Upgrade your chair or your computer?
  7. Dress code: smart or casual?
  8. Unlimited tea and coffee or unlimited snacks?
  9. Fruit or chocolate?
  10. Tidy desk or messy desk?
  11. Are you more likely to have a snack stash or stationary stash in your desk?
  12. Work through lunch or take a break?
  13. Holiday party or company retreat?
  14. Would you rather have a private office or designated parking spot?
  15. Office too hot or too cold?

Remote Work This or That Questions

The pandemic catapulted remote working into the limelight and it shows no signs of going away. In 2022, the number of people choosing to work remotely increased by 24% over 2021, according to a study by Owl Labs. So it's pretty likely you'll have some folks on your team who work remotely, or you'll work remotely yourself. 

But nearly half of the respondents reported feeling isolated from their colleagues while working remotely during the pandemic, a Glassdoor study found. These icebreaker questions give people a chance to connect and have fun with their colleagues in what can sometimes feel like a lonely environment. Here are some this or that questions related to remote work, to help you get to know your remote colleagues and their work preferences a bit better.

  1. Slack or Teams?
  2. Fixed work hours or flexible schedule?
  3. Work at home or from a coffee shop?
  4. Sweatpants and comfy clothes or smart work outfit?
  5. Camera on or off for work calls?
  6. 1:1 chats or group virtual meetings?
  7. Work at a table or on the sofa?
  8. Pets in your "office" or pets not allowed?
  9. Virtual background or keepin’ it real?
  10. Synchronous or asynchronous work style?
  11. Fully remote or hybrid working?
  12. Meetings at the start or end of the day?
  13. Netflix at lunch or lunchtime workout?
  14. Remote forever or back to the office?
  15. Team building online or in person?

Fun This or That Questions

Your this or that questions don't need to be all about work. They're also a nice way to get to know people more personally. Here are some this or that questions that are a bit more fun (though some of them are still loosely related to work):

  1. Coffee or tea?
  2. Summer vacation or winter holiday?
  3. Cats or dogs?
  4. Make food from scratch or order in?
  5. Get a raise or get a bonus?
  6. Watch the movie or read the book?
  7. Beach trip or trip to the mountains?
  8. Sweet snacks or savory snacks?
  9. Inbox zero or 100+ unread emails?
  10. One long message or messages



  1. A raise or more PTO?
  2. Be able to type really quickly or read really fast?
  3. Add colleagues on social media or keep personal life separate?
  4. Salad or sandwich for lunch?
  5. Drinks after work or team lunch?
  6. Team socials or whole company socials?

Productivity This or That Questions

Let’s dive into the nitty-gritty of how we all like to get stuff done! Are you the planner with every minute accounted for, or do you prefer riding the wave of inspiration as it comes? These questions peel back the layers of our work habits to find out what really makes us tick and how we can mesh our productivity puzzles together for a masterpiece of efficiency.
Work by lists or wing it?

  1. Detailed planning or big picture focus?

  2. Start projects early or work under pressure?

  3. Use multiple monitors or a single screen?

  4. Daily to-do list or weekly plans?

  5. Prioritize tasks by deadline or importance?

  6. Strict deadlines or open timelines?

  7. Weekly planning meeting or daily stand-ups?

  8. Set personal work goals or team objectives?

Work Environment
This or That Questions

Imagine your ideal workspace. Is it a jungle of plants and personal mementos or a zen-like temple of minimalism? Through these questions, we’re on a mission to discover what makes our workspaces feel like a second home. Let’s figure out how we can spruce up our square footage to make everyone’s day brighter and better.

  1. Desk plants or minimalist space?

  2. Quiet workspace or bustling office?

  3. Personal office decor or company-branded?

  4. Office snacks or bring your own?

  5. Water cooler chats or stay at your desk?

  6. Shared workspaces or personal offices for concentration?

  7. Dress-down Fridays or uniform work attire?

  8. Ergonomic accessories or traditional desk setup?

Communication This or That Questions

In the grand symphony of our workplace, communication and collaboration are the melodies that keep us in tune. But how do we prefer to hit those notes? Are we soloists or do we rock better as a band? These queries aim to decode our communication concertos and collaborative compositions, making sure every voice is heard in harmony.

  1. Team brainstorming or individual research?

  2. Take notes during meetings or listen and absorb?

  3. Face-to-face feedback or written feedback?

  4. Use emojis in work chats or keep it formal?
Coffee breaks or stretch breaks?

  5. Celebrate successes big or small?

  6. One-on-one mentoring or group training sessions?

  7. Use project management software or email for coordination?

  8. Company newsletter or team chat updates?

Technology This or That Questions

In the toolbox of our daily grind, are we more old-school hammers and nails or cutting-edge power tools? This segment is all about uncovering our tech tendencies and gadget go-tos. Let’s discover which tools empower us to build our ideas into reality and how we can integrate the best of both worlds into our workflow symphony.

  1. Use physical notebooks or digital notes?

  2. Handwritten memos or digital reminders?

  3. Use a planner or a scheduling app?

  4. Use tech gadgets or keep it simple?

  5. Brainstorm with markers and whiteboard or digital tools?

  6. Virtual sticky notes or physical post-its?

  7. Use a mouse or touchpad?

  8. External hard drives or cloud storage?

Personal Development This or That Questions

Ever think about what fuels your brain engine? Are we seeking adrenaline-packed seminars or the quiet contemplation of an online course? Here, we're curious cats, exploring the alleyways of learning and growth to satisfy our professional curiosity. Let's chat about how we keep our brainwaves surfing the edge of innovation and self-improvement.

  1. Learn on the job or professional development courses?

  2. Attend workshops or webinars?

  3. In-house training or external conferences?

  4. In-person training or online courses?

Work Habits This or That Questions

Dive into the quirks and features of our workday rides! Are you cruising in the fast lane with your tasks lined up like dominoes, or are you off-roading, taking the path less traveled by? These questions are your GPS through the landscape of work habits, guiding us to understand the unique journeys we each take to get through our to-do lists.

  1. Early bird or night owl?

  2. Brainstorming sessions or solo ideation?

  3. Standing desk or traditional sitting?

  4. Organize emails meticulously or keep a cluttered inbox?

  5. Organize files in folders or keep on desktop?

  6. Time tracking software or honor system?

Company Culture This or That Questions

What’s the secret sauce to our team’s spirit? Is it the epic saga of our annual retreats or the everyday magic of coffee breaks together? Here, we’re on a treasure hunt for the gems that make our team and company culture shine. Let’s share the moments and traditions that keep our collective hearts beating and our work meaningful.

  1. Office games or no distractions?

  2. Team socials or whole company socials?

  3. Annual company picnic or monthly team outings?  

This or That Questions

Welcome to the potluck of queries, where the questions are as varied as the dishes at a family gathering! From your battle between coffee and tea to your stance on inbox management, these are the spices of our workplace life. Let’s dish out our preferences and tastes, discovering the flavors that make our work family unique.

  1. Dress code: smart or casual?

  2. Lunch meeting or walking meeting?
  3. Get a raise or get a bonus?

  4. Inbox zero or 100+ unread emails?

  5. Traditional business cards or digital contacts?

  6. Voice memos or written notes?

Boost Retention With Employees Engagement

Icebreaker games like asking this or that questions offer many benefits for your employees. They encourage connection and bring a bit of fun into the workplace, helping people feel engaged with each other — and the company. 

Pairing regular icebreakers with a comprehensive wellness program can give employee engagement and retention a real boost. In fact, our research shows 92% of company leaders believe wellness programs are important for employee retention. Wellness programs provide a holistic approach to employee wellbeing, encompassing physical fitness and emotional wellbeing. 

If you want to learn what a wellness program can do for employee engagement, reach out to a Wellhub wellbeing specialist today. 

Company healthcare costs drop by up to 35% with Wellhub! (* Based on proprietary research comparing healthcare costs of active Wellhub users to non-users.) Talk to a Wellbeing Specialist to see how we can help reduce your healthcare spending!



Wellhub Editorial Team

The Wellhub Editorial Team empowers HR leaders to support worker wellbeing. Our original research, trend analyses, and helpful how-tos provide the tools they need to improve workforce wellness in today's fast-shifting professional landscape.


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