Let’s Play! How to Create the Perfect Blended Virtual Retreat Experience


Our Workplaceless team is proudly fully remote and globally distributed. However, we still get giddy whenever we get the chance to connect in person, and we normally aim to meet in person once or twice a year. With the travel restrictions in 2020 and into 2021, we weren’t able to make it happen, but we all needed the opportunity to connect as if we were together. So we set out to plan a synchronous and asynchronous virtual team retreat.

 Planning the Retreat.

We started planning two months prior to our targeted retreat timing.

  • Select a planning committee. We wanted elements of our retreat to remain a surprise, so we selected a small planning committee and delegated responsibilities for organizing activities based on expertise and interest.
  • Set goals. Outlining goals for the retreat will help team members see value in the event and help them focus on the aspects that are most important. Thinking about purpose first makes planning easier, because you’re less likely to try to fit too much into the schedule. Our three goals were:
    1. Leave feeling more connected to one another.
    2. Solve a Workplaceless strategic problem together.
    3. Have fun.
  • Document ideas and decisions. One of our first steps was to create planning documents that we could collaborate on asynchronously. We knew this wouldn’t be our only virtual retreat, so it was nice to have a place to document ideas we didn’t move forward with that we could pick-up for future events. Information to consider including in a planning document includes: scheduling and availability preferences, activity ideas, and ownership of planning. 
  • Establish a theme. Having a unifying theme can help to build excitement, but it also helps to make decisions about whether or not to include specific activities easier. Our theme was “Let’s Play” an evolution of “Work Place Less” → “Work, Play, Let’s” 

  • Set a budget. Consider the goals and scale of the retreat when setting a budget. 
  • Block sync meeting time on calendars. We reached out early to team members to ensure we selected weeks that worked best for the most of our employees. We limited the sync time for our retreat for two hours during three days of our retreat week.
  • Decide what activities can be done async or sync. We were intentional about making our synchronous sessions as valuable as possible. We chose to focus on connecting and problem solving as the primary categories of tasks for these sessions, which helped us determine what we should do with that time. 
  • Book with outsourced vendors. While we love planning retreats ourselves, it’s also fun to bring in experts to lighten the load of the planning work, and to introduce new energy into the activities. To fit with our “fun” goal we booked the Art Heist game with TeamBuilding.com. Since one of our goals was also to connect with one another, we also took the Clifton Strengthsfinder assessment and incorporated our results into various activities. 


Prepping the Retreat.

The week before the retreat we shifted our focus to finalizing details and drumming up excitement across our teams.

  • Send out a retreat SWAG bag. We selected a variety of items in advance for our “Play Pack”—all of which connected to our theme of play. We also sent a sneak preview of the pack to get people guessing and excited about what was coming. 

  • Finalize the daily agenda. For everything to run smoothly, the week before our retreat kicked off we started finalizing details. Lean into the theme from the start! Our week included: 
    • Day 1 of Play: Let the Games Begin!
    • Day 2 of Play: Work Hard. Play Hard. 
    • Day 3 of Play: Closing Ceremony
  • Create a communication channel. Let attendees know where to go to receive and respond to details about the retreat. We created a Slack channel, specifically for our retreat called #lets_play_retreat.
  • Finalize resources. We used a combination of MURALs and a Slack bot we created centered around play. 
  • Encourage use of an Out of Office autoresponder. We thrive with boundary and expectation setting. We wanted our team members to be able to be fully focused on our virtual retreat, so we drafted a sample Out of Office message to give our team the mental freedom to fully participate.
  • Assign any prework. Particularly for our session where we aimed to “solve a Workplaceless strategic problem together,” we wanted team members to come prepared to add value so some advanced review of existing documents and decisions were in order. 


The Retreat!

Here’s how our event went:

  • Start with energy. We sent our agenda out to the team including a video from our CEO to set the tone of play. In keeping with our theme, the agenda was a gameboard. We asked team members to select their game piece to keep track of their game progress.

  • Start async activities. A couple of ours included:
    1. Our Slack channel Slack bot kicked off a game of “Two Truths and a Lie” voted on by emojis.
    2. We started a 40 hour Async Scavenger Hunt based on points. 
    3. We were inspired by Doist for our own version of async telephone.

  • Cherish sync time. Within the three two-hour blocks we dedicated to spending time together, each activity was selected with intention to align with our goals. 
    1. We thoroughly enjoyed the Art Heist via Team Building
    2. We spent one sync session together focusing on a critical pillar of our 2020 strategic plan. 
    3. We created and tested out a couple sync games to play live, including: work-safe “Never Have I Ever” and Zoom Charades. 
    4. We allocated time for team members to get outside and enjoy “walkie-talkie” 1:1 catch-ups with one another.
  • Bring it all together. We wanted our closing ceremony to bring us together and to continue to celebrate play yet pull together activities that occurred throughout the week. Via the Async Scavenger Hunt, we learned a variety of things about our teammates that we were able to highlight in a slideshow with accompanying soundtrack for the event and showcase insights about one another. 

Reflecting on the Retreat

Here’s how we followed up:

  1. Collect Feedback. We created space to ensure that our team members could give us you honest feedback about the retreat. 
  2. Keep the Party Going. As with any time investment, we hoped to learn something new about our team together. No matter how big or how small, we take those findings into the future. We loved the spirit of play and little moments to connect in async ways, so we decided to keep our play bot alive and well.  

We’d be happy to share our insights on planning virtual retreats that help to cultivate a strong remote culture. Let’s schedule time to connect.

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Workplaceless Team

Workplaceless Team

Workplaceless envisions a workforce that thrives in a flexible and digital-first future—where performance and growth are not constrained by location. Our team goal is to share insights and practices that will help professionals and companies achieve this aspiration.
Workplaceless envisions a workforce that thrives in a flexible and digital-first future—where performance and growth are not constrained by location. Our team goal is to share insights and practices that will help professionals and companies achieve this aspiration.
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