60 Team Building Questions for Remote Workers

A group of remote workers getting to know each other

It doesn’t matter if you’re talking about 5 remote team members, or 50, it takes effort for coworkers (and managers!) to get acquainted with each other. There’s no physical water cooler, no collaborative stand-up meetings, or long lunches to help facilitate togetherness.

It’s incredibly important to have a bond with your remote team members, and coming up with team building questions can go a long way to help with that. With that in mind, I’ve listed out several questions that can give you a headstart in that regard. These team building questions are categorized by situation, that way you can take your pick based on the personality of your remote employee.

Ice Breakers and Personal Introduction

Questions in this category are designed to help team members get to know each other after meeting. Helping remote coworkers and employees feel comfortable right away is very important. The questions should aim to disarm them and make them feel more just vulnerable enough to give some great answers to the team building questions. I would suggest including questions about hobbies, interests, backgrounds, or even what kind of pets they have!

Many of the team building questions in subsequent sections will relate to movies, pets, and history, so you might try to include things like that in the ice breaker questions.

  • What’s your favorite book/movie/TV show, and why do you love it?
  • If you could learn any new skill or hobby without any effort, what would it be?
  • If you could be any character from a book or movie for a day, who would you choose and what would you do?
  • Imagine you’re an inventor…What whimsical or unusual invention would you create?
  • If you had to live in a video game world for an entire month, which game would you choose and why?
  • What would your dream house look like if you were to build it in a fantasy world or another planet?

Work Environment and Home Office Setup

For remote workers like ourselves, our workspace is basically sacred. It doesn’t matter if we’re at home, at an Airbnb castle, or on a tropical island, having a productive workspace is incredibly important. For this reason, our personal preferences (as it relates to workspace) is such a good type of team building question.

These questions should encourage team members to share insights about their home office setup, daily routines, and personal touches that make their workspace comfortable and productive. It’s an opportunity to explore the individual challenges and advantages of remote working spaces, no matter what type of place they work from.

Questions that prompt discussions about ergonomic setups, favorite gadgets, or even the views from their desk are great options to include! Since remote work often blurs the lines between personal and professional life, these questions can also offer a glimpse into the personal lives of team members.

  • What’s one item in your home office that you can’t work without?
  • Do you have any routines or rituals that help you start your workday?
  • If you could invent a new piece of home office technology, what would it be and how would it work?
  • Share a ‘work from home’ myth you believed in and tell us how your experience has debunked it.
  • If you could have any fictional character as your virtual assistant for a day, who would it be and why?
  • If you could share your workspace with any historical figure for a day, who would it be and what would you hope to learn from them?

Communication and Collaboration

Good communication is the lifeline of remote work, it simply can’t work without it. These questions are designed to uncover the tools, strategies, and personal preferences that make this possible. They should encourage team members to reflect on their communication styles, as well as the nuances of non-verbal communication, tone, and timing in a digital world.

Questions might explore preferences for video calls vs messaging, how to handle misunderstandings in a virtual environment, or creative ways to maintain team cohesion. This category is crucial for identifying areas where communication can be improved and for celebrating the unique ways in which team members connect and work together even though they aren’t in the same physical space.

  • How do you overcome the challenges of not being able to communicate face-to-face?
  • Can you share an experience where effective communication significantly benefited a project?
  • If you could create a new, innovative communication tool for remote teams, what unique feature would it have?
  • Imagine if our team communication was like a sci-fi movie. How would futuristic technology change the way we interact?
  • If you had to describe your communication style as a weather phenomenon, what would it be and why?
  • What if we had a team mascot that represented our communication style? What would it be and what qualities would it embody?

Work-Life Balance

The boundaries between personal and professional life can often become blurred, making it essential to consciously address balance and well-being. In my experience, this usually isn’t much of an issue, but it can leave us (remote workers) more susceptible to getting burned out.

These questions should encourage team members to share their strategies for disconnecting from work, managing stress, and maintaining a healthy lifestyle. They can also explore the unique challenges and solutions related to remote work, such as creating a dedicated workspace, dealing with isolation and loneliness, or staying physically active. This is an opportunity for team members to learn from each other’s experiences, and maybe even to gain new ideas for enhancing their work-life balance.

  • How do you create a clear distinction between ‘work time’ and ‘personal time’ when working from home?
  • What’s your favorite way to unwind or take a break during a busy workday?
  • If you could have a fictional character as your personal life coach, who would it be and what life lesson would you want to learn from them?
  • What if you could teleport to any place in the world for your lunch break? Where would you go and what would you do?
  • If you could invent a magical device to improve your home work-life, what would it do and how would it look?
  • Imagine a world where your pet (or a dream pet) could talk during your workday. What advice do you think they would give you about work-life balance?

Challenges and Solutions in Remote Work

As agile and nimble as remote work can be, remote workers also have unique challenges. For instance, I once had an e-commerce client that we were doing SEO for…but they were in Australia. Take it from me, anything in the Oceania region is difficult to work with from a time zone standpoint (I’m in the US). We had calls that started so early in the morning (my time), that sometimes I would just stay up half the night to take it and then just sleep in. Those were some looooooong days.

Questions here can have a wide range of subjects. In fact, I would tailor these questions differently if you are asking them to medium to high-level managers. Many of the challenges for managers relates directly to staff, so take this into consideration when putting together questions of your own in this section.

The questions here should be designed to get them to reflect on their personal experiences with these challenges. This goes a long way to fostering a problem-solving mindset within the team. This is also a space for imaginative thinking – considering how hypothetical scenarios or innovative technologies could enhance remote working experiences.

  • What has been your biggest challenge working remotely and how have you addressed it?
  • How do you stay motivated and productive when working alone?
  • If you could get advice from a historical figure about overcoming challenges, who would it be and what would you ask?
  • Imagine a day where everything that could go wrong with remote work does. How would you handle it, and what would you learn?
  • If you were to write a sci-fi story about a remote worker overcoming extraordinary challenges, what would be the main plot?
  • What if you discovered a hidden virtual world inside your computer that could solve any remote work challenge? Describe your first adventure in it.

Team Goals and Objectives

I’m a marketer, so I often take the “if you don’t track it you can’t get better” mindset. The questions here should be sculpted to better understand the team’s goals, and more importantly, what they are doing to accomplish them.

This is also an opportunity to explore how team members envision their growth within the team and the support they need to achieve their aspirations. By openly discussing these topics, the team can strengthen its alignment, ensure everyone is working towards common goals, and identify opportunities for growth and development.

  • What personal or professional goal are you currently working towards, and how does it align with our team’s objectives?
  • How do you see your role evolving in the team, and what support do you need to achieve this growth?
  • If you could lead a project of your choosing, what would it be and how would it benefit the team?
  • Imagine our team is a crew on a space mission. What role would you play, and what unique skills would you bring to ensure the mission’s success?
  • If you could gain one superpower to help you achieve your goals faster, what would it be and why?
  • What if our team had an anthem or theme song that played at the start of each meeting? What would it be and how does it reflect our goals?

Feedback and Improvement

Feedback is a powerful tool for personal and professional growth, especially in a remote setting where direct interactions are limited. The problem I ran into with my team was that they wouldn’t ask for feedback in the first place. This was much more a fault of mine than theirs. However, when I learned this, I started to make a deliberate point to ask more questions about an assignment. That would usually get them to open up a lot more.

Similar to the communication questions, feedback team building questions give everyone a chance to discuss the importance of constructive criticism, the challenges of communicating feedback remotely, and the ways in which feedback can be used positively.

  • What’s one piece of constructive feedback you’ve received in your career that made a significant impact on your work?
  • How do you prefer to receive feedback, and what makes it most effective for you?
  • If you could get feedback from any historical figure, who would it be and what would you want to learn from them?
  • Imagine a future where AI provides instant feedback on your work. What would you want it to analyze and why?
  • If your work life was a video game, what feedback or ‘game tips’ would you expect to see pop up on the screen?
  • What if you had a personal cheerleader who gave you feedback every day? What encouraging words or phrases would you want to hear?

Cultural Exchange and Diversity

Remote teams often consist of members from various cultural backgrounds, and this diversity can be a tremendous asset. The questions here aim to encourage team members to share their cultural heritage, traditions, and perspectives.

This sharing not only enhances mutual understanding and respect but also enriches the team’s collective experience. And from a practical standpoint, it can help better understand things from a managerial standpoint as well. Days off for different holidays, what kind of projects they can’t work on (per religion, personal preference, etc).

Discussions can revolve around cultural influences on work styles, communication, and problem-solving approaches. This is an opportunity for team members to express pride in their cultural identity and for others to broaden their cultural awareness. One word of warning though: try and make sure none of your questions are unknowingly insensitive or intrusive. You might be surprised at what some cultures find offensive or are looked at as overstepping.

  • Can you share a tradition or custom from your culture that you find meaningful or enjoyable?
  • How has your cultural background influenced your approach to work and collaboration?
  • If you could host a virtual cultural exchange event for our team, what activities or experiences would you include?
  • Imagine a festival from your culture being celebrated by the whole team. What unique aspects would you want everyone to experience?
  • If you could create a new holiday that combines elements from different cultures represented in our team, what would it look like?
  • Imagine you’re taking the team on a virtual tour of your hometown or country. What are three must-see places or experiences you would include and why?

Innovation and Creativity

It becomes even more important to actively encourage creative thinking and innovative approaches to work when a team is remote. It’s like a fire that needs to be poked every once in a while. If you don’t nurture it, eventually it will die out.

The questions in this category should inspire team members to think outside the box, share their creative ideas, and discuss how innovation can be applied in their daily tasks and long-term projects. This is a chance to explore how each team member views what inspires them, and how they overcome creative blocks (this is especially important for certain roles). Discussions can also focus in on fostering creativity and how the team can collectively create an environment that nurtures and values innovative thinking.

  • What’s one innovative change you’ve made to your work routine that has significantly helped you?
  • Can you think of a recent project where a creative approach solved a challenging problem?
  • If you could collaborate with any inventor or creative mind from history on a project, who would it be and what would you create?
  • Imagine if our team was tasked with inventing a new planet. What unique features would it have and how would they facilitate remote work?
  • What if you had the ability to bring any fictional technology to life for our team’s use? What would it be and how would it change our work?
  • If you could design a virtual reality world for our team meetings, what would it look like and what interactive elements would you include?

Fun and Engagement

Don’t forget the fun questions! The team building questions in this category should encourage team members to share what brings them joy and laughter, their ideas for fun team activities, and how they like to engage with colleagues in a relaxed setting.

This is an opportunity to brainstorm on quirky traditions, or creative ways to celebrate achievements and milestones. It’s about creating memorable experiences that foster a sense of community and belonging, making remote work not just productive but also delightful.

  • What’s your favorite way to have fun or relax during a virtual team hangout?
  • If you could organize a virtual team-building activity, what would it be and why?
  • Imagine if our team could go on a virtual adventure together. Where would we go and what would we do?
  • If you had to choose a theme for a team costume party, what would it be and what would you dress up as?
  • What if we had a team mascot that only communicated in riddles? What riddle would it tell us today?
  • If our team was in a band, what instrument would each person play, and what genre of music would we perform?
Founder : Wherever I May Work | Website | Other Posts

Jared has worked remotely for 15 years in various marketing capacities, and has managed hundreds of marketing campaigns along the way. He has held freelance, agency, and in-house positions for companies large and small.

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