Holding a virtual offsite? Our tips for fun and team-building

Holding a virtual offsite? Our tips for fun and team-building
By Isabella Chiu | On Jan 11, 2022
6 min read

For distributed or remote teams, meeting in person (what we call an “in-person offsite”) is crucial. It helps everyone get to know each other and form the meaningful connections necessary for turning a group of individuals into a cohesive team working toward common goals.

Of course, during the COVID-19 pandemic, meetings like this have had to be put on hold for everyone’s safety. Everyone at TestBox was hugely disappointed to miss the opportunity for an in-person event. So, we decided to put together a virtual offsite and make it awesome!

Since this was our first time planning a virtual offsite, we spent some time researching what other teams do. Sadly, there weren’t many resources available, which is why we thought we’d share our process and how it all turned out.

In this article:

Our goals

We started our planning by making a list of goals. We asked ourselves: What do we hope to achieve by bringing the team together virtually?

Your goals will likely be different, but here’s what was important for our team:

  • Make time for lots of fun.
  • Leave time for decompressing between sessions.
  • Prioritize team bonding and feeling rested like we would if we could have traveled to a fun place together (e.g., having a day dedicated to fun and keeping the last day more relaxed as it would have been a travel day for most attendees).
  • Optimize the timing to be inclusive of our whole global team. This meant making certain tradeoffs and asking team members to be flexible with their time. We decided to start later in the day for those on East Coast time and run into the evenings so it would be easier for our West Coast and Australian team members to attend. 

Our schedule of activities

We decided to include the following activities in our schedule:

  • Reflection sessions
  • DEIB (diversity, equity, inclusion, and belonging) workshops
  • An Engineering team session
  • A hackathon
  • Meals and games time

We deliberately scheduled our more intensive sessions for early in the week while we were all fresh. For meals, we ate together as the entire team, in smaller teams, or other randomly organized groups, such as by time zone. Since we scheduled the fun events in the evenings, we made these optional and invited people to bring a +1. 

Here’s the schedule we built:

Team reflections

At TestBox, we’re firm believers in the value of open conversations, so we’ve held a Team Reflections session before. We find this to be a powerful way to get everyone on the same page. It generates a lot of excitement and helps us dream big.

For the offsite, we asked everyone to reflect on the following questions:

  • What are the product goals you would like us to achieve by the end of this year?
  • What about the end of next year?
  • What do you think we are doing really well as a company?
  • What do you think we are not doing as well as you’d imagined, given we’re six months into our journey as a company?
  • What are you most excited about when you think about TestBox and our potential?

We also focused part of the session on vulnerability and sharing our individual professional development goals (we talk more about why this is important in our previous post). The idea of being vulnerable is based on the philosophy shared by Adam Grant in his podcast — Adam suggests that one moment of vulnerability leads to a full year of psychological safety.

Creating a safe environment for a team has to be done through leading by example. Simply asking team members for feedback isn’t enough — leaders have to show that when they receive feedback, they are open to it and won’t become defensive. At our offsite, Sam and Peter shared professional development areas where they have each struggled in the past. They also outlined areas where they want to improve and how the team can support them. This made it safe for everyone in the team to join in and share their own goals and how the team could empower them.

To get people thinking about their professional development goals, we asked these questions:

  • What professional development goals have you previously worked on and now have relative mastery at?
  • What are you currently working on, or would you like to start tackling for your professional development?
  • What has held you back from progressing on these development goals?
  • How can we, as a team, support you in working toward these goals?

Gift exchange

A gift exchange is always fun! For this event, we assigned everyone a giftee in advance. We asked everyone to put together a gift that represented their location. For instance, being from Canada, my gift included Roots socks, maple syrup tea, and Canadian candy. A team member from North Carolina sent their giftee a Duck Donuts shirt and mug. We encouraged people to buy and pack their gifts by hand for a personal touch. This helped bring a physical element of togetherness to the week. 

Games and challenges

We held games and challenges throughout the week, including a scavenger hunt, daily mini-challenges, and the hackathon. The overall winner, the person with the most points, received a gift card and the privilege of picking the next type of team swag we should order.

Daily challenges included: 

  • Draw the best self-portrait while wearing a blindfold.
  • In five minutes, turn your bathroom into the sort of venue you might visit for a great night out. Best bathroom conversion wins!
  • Throw a tea bag into a cup from the furthest distance.

Two examples of our blindfolded self-portrait 

An example from our scavenger hunt, where I couldn’t find a cactus so I pretended to be the cactus myself 

The team playing hide and seek – Jake was the leader of the round and the rest of the team hid successfully

As a quick aside, we did get mixed feedback on some of the challenges. It turns out that they might have been a bit disruptive to roommates and others at home (oops!) — so, keep this in mind when you’re coming up with ideas for your team.


We thrive on exploring new ideas, so we wanted to give the team a chance to think outside the box and investigate concepts that we haven’t been able to fit onto our regular roadmap. We also wanted to create an opportunity for different folks to work together — sometimes these collaborations can result in unexpectedly wonderful contributions.

We split the team into groups of three (pre-planned so we could balance engineering resources, personalities, time zones, and other considerations). Each group had time to brainstorm ideas, and then the executive team reviewed the ideas to make sure there was no overlap and provided extra input where it made sense. The groups had free rein to build as they needed. We set aside two hours to explore all the hackathon projects before our final presentations so people could brainstorm questions to ask in advance.

Getting people into different spaces

One of the things we like about in-person offsites is the opportunity to get out of the office and away from our usual surroundings. We find that it gives us a new perspective and opens us up to thinking about things in new ways.

To do this virtually, we decided to hold our kickoff breakfast/lunch at cafes that were local to each of us. We encouraged everyone to pick a place they were comfortable going to — whether that was indoors at a cafe, on a patio, or in a garden. This also meant we could be mindful of everyone’s COVID-19 restrictions wherever they were. To further simulate a real offsite, we provided a budget for ordering something yummy to eat.

We also played a round of games at local parks. In advance, we asked people to answer a series of cryptic questions, such as:

  • I like to go to the park and watch _________________.
  • My favorite kind of car is a ________________________.
  • If I could build a house from scratch, it would be made out of ______[color] ________[material]. 

The blanks became the basis of a scavenger hunt, which had us exploring our local parks looking for those objects. We shared photos of what we found on Slack and voted on the best answers to give points. There were some hilarious photos and tons of laughs, as well as extra steps and fresh air that day!

Tools we found helpful

It doesn’t take much in the way of tools to create a virtual offsite, so don’t worry that you’ll have to amp up your tech stack to make it awesome. Sometimes, simple is best.

Here are the tools we used: 

  • Gather: We loved meeting in the virtual Gather town because it let us wander around a virtual office and meet in groups of various sizes. 
  • Google Meet or Zoom: We used these tools when we needed to record a session if the full team would not be there. For our sessions in cafes and parks, we used Zoom so folks could dial in by phone if they needed to.
  • Miro: We found this virtual whiteboard great for brainstorming sessions. It let everyone leave sticky notes, and we could arrange and rearrange them throughout our conversation.
  • Slack: We used a Slack channel to chat and share photos.

Lessons for next time

The most important lesson, I think, is to make a real commitment to the event. We made it very clear during the weeks leading up to the event that there was no expectation for anyone to be doing “normal” work. We wanted people to bring their full energy and excitement to the offsite rather than splitting their attention with their usual work. We planned accordingly to account for a week of team downtime.

Other lessons we learned:

  • Add more of a time buffer. We consistently underestimate how much time it takes for the team to share reflections. We suggest breaking up the more involved reflection-heavy sessions across several days. Holding the reflections session on Monday, followed by the DEIB workshop on Tuesday, felt like overload.
  • Add more structure to the team meals. We found it a bit weird to sit and eat with others virtually, so we might add a moderated activity the next time. That way, if someone doesn’t want to eat at that time, they can still participate. Examples could be playing a game, watching a video or movie, or having specific topics to discuss. 
  • Reduce the number of games and challenges. Looking back, we had a lot of these activities. While it created a lot of chances for the team to get silly and have fun with each other, some of us did find it exhausting.
  • Add cross-functional sharing sessions. One of our team members expressed that they wanted to learn more about what others do in their different roles. An offsite would be a great chance to talk about the work other people do, so everyone understands how we all fit into the team.

Personally, I thoroughly enjoyed our virtual offsite and having a chance to get to know the rest of our team better. I think the connections we built will really help us work together more effectively. Hopefully, you’ll find some inspiration here to help you put together one of these events for your distributed or remote team.

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Isabella Chiu

Hi, I'm Isabella! I'm a proud Canadian with extensive tech strategy experience. I'm passionate about making complex processes easier and more efficient. There's nothing in my life I haven’t tried to optimize.

When I'm not making spreadsheets, I enjoy drawing (I published a kids' book, Let's Get Boba!), cooking, and spending time with friends and family.

TestBox empowers you to have a self-serve, customer-led experience so you can buy new software and feel confident that you made the right choice. Currently focused on Customer Support, TestBox allows you to test out Zendesk, Freshdesk, HubSpot, Dixa, and other products side-by-side. It takes a matter of minutes to sign up and take these products for a test drive. Find out more at TestBox.com or follow on LinkedIn.