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How To Plan a Virtual Offsite for a Distributed Team

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In January 2020, Loommates from around the world gathered in Barbados for our annual offsite — a special time for our globally distributed team to relax, bond, and create lifelong memories together.

Little did we know that, one year later, we’d find ourselves in a very different scenario.

We thought about postponing our 2021 offsite to a later date or organizing small, local gatherings so Loommates could still get together in-person. But with an unclear vaccine timeline, neither of those options were feasible. 

After months of working from home due to COVID-19, we knew we couldn’t just spend an entire week in Zoom meetings, though. So we pushed the boundaries of what we could do virtually, and we designed our offsite around virtual reality. 

Here’s how we successfully pulled off our first-ever virtual offsite, and some tips for how you can do the same.

7 suggestions for planning a successful virtual offsite 

1. Find ways to connect outside of Zoom calls.

When we first started planning our virtual offsite, we didn’t think there was much leeway when it came to planning virtual events apart from scheduling back-to-back Zoom calls. That is, until Loom Co-founder and CEO Joe Thomas suggested exploring the idea of virtual reality.

In non-pandemic circumstances, we’d be coordinating flights and accommodations for more than 100 employees to a single destination. With virtual reality, we were able to send everyone an Oculus Quest 2 headset to bring the virtual world to them. Plus, we were able to limit Zoom content to only two hours per day to keep the content engaging.

Once we confirmed that virtual reality would be a feasible medium for our offsite, I and a select few Loommates had the “difficult” job of trying out different kinds of VR apps. We ultimately chose SculptrVR and Wander, but there were plenty of others that would have worked equally well for team-building purposes. 

2. Get perspectives and ideas from outside of your People team.

Offsites are an opportune time for a team to interact with each other as people, not just as colleagues. Forming an offsite committee helps democratize the brainstorming process and makes it easier to put together a schedule your employees will be excited about.

Back in mid-October, we sent all Loommates a Google Form to solicit ideas for the offsite, along with a sign-up sheet for those interested in joining the offsite committee — from new hires to members of the Leadership team — to bring those ideas to life. 

Our offsite committee was instrumental in creating an offsite schedule that reflected Loom’s culture, including choosing a virtual reality format, serving as the week’s emcees, and coordinating our very first “LooMTV Cribs” screening. 

Senior Communication Designer Tim Lampe and Enterprise Support Specialist Jaclyn Thompson announced the official offsite schedule as emcees Chip and Babs.

Customer Marketing Manager Allie Hitchcock takes us on a tour of her Washington, D.C. workspace as part of our LooMTV Cribs screening. 

Additionally, Loom’s Brand team conceptualized our official offsite theme of “Here, There, Anywhere” and designed bright, tie-dyed t-shirts for everyone in the company.

Senior Director of Brand Stewart Scott-Curran explains why he and the Design team created t-shirts for the offsite. 

Pro tips:

  • Once you’ve settled on a date for your virtual offsite, form your committee at least 3-4 months in advance to ensure you have enough time to decide on your schedule, pull events together, and design and send out swag. 

  • Don’t make the committee formation process too complicated — simply have employees add their name to a doc and go from there! 

  • Schedule weekly syncs and check-ins to ensure you’re staying on track.

  • Use asynchronous communication to keep each other updated on your progress between syncs.

3. Create a virtual meeting place.

Loom offsites have always taken place in warm, beachy locales: Mexico in 2017, Costa Rica in 2019, and Barbados in 2020. We wanted to carry out tradition as best as possible while acknowledging the unique circumstances of this year.

We teamed up with Active Replica to create our unique, virtual island getaway called “Loom by the Sea.” Open 24/7 during our offsite week, Loom by the Sea became the virtual gathering spot for icebreakers, watercooler conversations, and happy hours.

Loom By the Sea screenshot
Loom By the Sea was accessible through virtual reality and desktop, offering our fully remote team a new, interactive way to meet up virtually and in real time.

Pro tips:

  • If you’re thinking of holding an offsite in virtual reality, don’t make VR-exclusive activities mandatory. Not everyone has (or wants to create) a Facebook account, making it impossible to use an Oculus device. Moreover, virtual reality can cause nausea, especially if used over long periods of time. Give participants the option to cast (VR-speak for stream) their activities online for those who don’t wish to participate so they’re still in on the fun!

  • Order virtual reality headsets as early as possible to give your team a chance to test them out and download any necessary apps well ahead of your offsite. Office Manager Tiffany York made sure every Loommate received their headset before or during our holiday break (about 1-2 weeks before the offsite began) so they could prepare ahead of time. 

4. Use asynchronous video messaging to create a shared experience.

From San Francisco to Lisbon to Auckland, Loommates live and work across the globe. To create a semblance of total togetherness like we’d have during an in-person offsite, we used Loom to stay connected. 

We created a dedicated offsite Slack channel so everyone could keep up with the schedule and activities, share screenshots and looms, and even plan unscheduled activities.

Loom virtual offsite Slack channel screenshot
Our virtual offsite Slack channel served as our centralized hub for updates, announcements, and memories.

Throughout the week, Loommates dropped looms of their time in Loom by the Sea so everyone at the company could create new memories together, even if they didn’t see the action unfold live. It was a great example of the impact asynchronous video messaging has on bringing distributed teams together. 

Staff Brand Strategist Brooks Chambers peeks into Engineering Manager Paulius Dragunas’ avatar head and contemplates the purpose of its tongue. Because he captured the moment on Loom, everyone in the company had a chance to experience the moment on their own time. 

Our offsite emcees, Chip and Babs, also delivered daily recaps made with Loom in the Slack channel to get everyone up to speed on the previous day’s events.

Chips and Babs virtual offsite agenda screenshot
Each day, offsite emcees Chip and Babs would provide a recap of the previous day’s events and share highlights.

Interestingly enough, we synchronized our favorite asynchronous moments to keep them fresh. Instead of holding a synchronous team talent show, for example, we simply watched our favorite Loom videos of the year for the very first time synchronously, both on Zoom and in Loom by the Sea. It was a simple event to put together, and it ended up being one of the crowd favorites. 

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5. Don’t schedule it like an in-person offsite. 

It’s easy to organize a set schedule of activities and meals for an in-person offsite. During a virtual offsite, however, everyone’s calendars are full of personal obligations, like child care and schooling, and they can’t dedicate 100% of their energy to connecting with teammates as they’d be able to do if they traveled away from home. We baked in enough unstructured time each day so everyone could be fully engaged in planned activities.

We also had the additional complication of navigating different time zones. Each day, we scheduled activities to cater specifically to EST/CST/European and PST/APAC time zones and scheduled a few events per day that overlapped well with all time zones so everyone in the company would have the opportunity to participate in them together.

Here’s a snapshot of our offsite schedule template, which we created in Notion. We kept daily activities light for four days to provide team members flexibility. 

Virtual offsite schedule Notion screenshot
Here’s a snapshot of our offsite schedule template, which we created in Notion. We kept daily activities light for four days to provide team members flexibility.

We were pleasantly surprised to see how many Loommates took advantage of unstructured time to start or participate in their own events.

Throughout the week, Loommates enjoyed impromptu Beat Saber competitions, played in a poker match, and even built a fully-stocked virtual bar in Loom by the Sea. Spontaneous activities like these helped us strengthen bonds virtually.

Paulius Beat saber Slack thread
When Engineering Manager Paulius Dragunas suggested holding a Beat Saber competition, an unofficial team bonding activity was born.
Ashwin virtual offsite casino game
Senior Software Engineer Ashwin Bhat organized a group poker game that took place in a virtual casino.
Loom by the Sea virtual dance floor
Teamwork makes … a dance floor and DJ booth operated by a narwhal inside of a pirate ship.

Now that you know how and when to plan your offsite schedule, the next step is determining what to plan. The goal of our offsite was twofold: team-building and having fun, and setting the stage for an incredible year ahead. 

We balanced each day with a team-building activity or two along with work-related ones. To kick off the week, Loom Co-founders Joe Thomas and Vinay Hiremath put together a presentation of Loom’s mission, vision, and strategy in the context of 2021, which served as the perfect warm-up activity for Loommates old and new. 

The following day, Joe moderated a fireside chat with former LinkedIn CEO and Executive Chairman Jeff Weiner, who shared his insights on what it takes to build successful teams and the most coveted leadership qualities. (Unsurprisingly, effective communication was a big one!)

Finally, as a company whose mission is to empower everyone to communicate more effectively, we wanted to schedule an activity around improving communication skills. On the third day of the offsite, we ran an interactive workshop with the help of communication coach Rachel Rodriguez, complete with small group activities in breakout rooms.

Communication workshop screenshot
Communication coach Rachel Rodriguez breaks down the building blocks of authentic, productive communication.

Pro tip:

  • Don’t make a hard-and-fast “no work” rule. Since we planned our offsite during a work week, we simply encouraged teams to keep work-related meetings as light as possible so everyone could enjoy themselves without stressing out too much about ongoing projects. 

6. Prioritize engaging, smaller group activities.

It’s difficult to create authentic bonds when you’re stuck behind a screen. To increase engagement and fuel new connections, we divided Loommates into teams of 4-6 according to their time zones. 

Throughout the week, we awarded points to teams based on their performances in various optional activities, such as the most creative team name and best pirate ship created in SculptrVR. The interactivity of virtual reality helped teammates feel like they were in the same room together.

SculptrVR pirate ship
For an interactive team-building exercise, groups met up in SculptrVR to build their own pirate ships. The winners earned points for their teams, and one of the pirate ships was uploaded to Loom By the Sea so all Loommates could visit it!

7. Go with the flow.

Not everything went as planned — and it was completely OK.

At the beginning of the offsite, we navigated through three major app outages, including on Slack, which made communicating a bit difficult. We temporarily resorted to email to get by.

We also encountered glitches and bugs in virtual reality. 

Business Operations Manager Raymond See virtually pokes Engineering Manager Paulius Dragunas.

And because SculptrVR doesn’t allow for private rooms, teams had surprise visitors help build their pirate ships.

Nicolette Slack thread SculptrVR room
When Senior Software Engineer Nicolette Yadegar mentioned a child had popped into her team’s SculptrVR room, other Loommates chimed in to say they’d experienced the same thing. We later realized the same child had been helping most teams build their pirate ships.

We took all of these hiccups in stride, and many of them are among our fondest memories of the offsite.

Further reading:

A Retreat Apart: Planning Help Scout’s First Ever Remote Retreat — Help Scout

How to Make Sure Your Virtual Offsite Doesn’t Suck — First Round Review

Energizing a company remotely: Learning from Miro’s 2020 virtual offsite — Miro

Virtual Offsites That Work — Harvard Business Review

How to Host a Virtual Offsite in a Pandemic — Front

The best virtual team building activities, according to full-time remote workers — Atlassian

The activity we didn’t get to

While the entire company participated in the communication workshop the afternoon of January 6, deadly riots broke out at the U.S. Capitol. Our PST and APAC groups were scheduled to explore the Wander virtual reality app later that day, which our EST/CST/Europe groups were scheduled to do the following morning.

Though Loommates were digesting the news miles apart, the sadness and devastation were palpable online. The Leadership team quickly decided to suspend the day’s remaining offsite activities to give everyone a chance to unplug and process.

We closely monitored the news and moved forward with the culminating event of the offsite the next afternoon: the Loomies awards ceremony. It was the perfect time to express gratitude for our teammates and enjoy some much-needed, lighthearted fun during a very bleak time.

Loomies awards screenshot
The Loomies included awards for our cultural values, Loom of the Year, Best LooMTV Cribs video, and in honor of a popular “joke of the day” Slack channel run by Business Operations Manager Rachel Li.

The team’s response to the events that unfolded was a powerful reminder that employees are people first. If you create a culture and activities that prioritize this concept, you’re better equipped to weather whatever challenges may arise.

Using virtual reality to stay connected beyond our annual team offsite

For our annual offsite this year, we took the plunge in pixelated waters and achieved just what we’d set out to do: strengthening team and company-wide connections and entering 2021 with renewed energy and perspective. 

While we can’t wait to have our next in-person get together, we’re excited to incorporate virtual reality and other elements of our first-ever virtual offsite into future company-wide events, onboarding, and virtual meetings when we need a welcome change from video calls to stay better connected as we continue to navigate hybrid remote work


Feb 8, 2021

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