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Plan a virtual retreat (five tips)

A computer screen displaying a virtual retreat with a group of people.

So, how do you plan a virtual retreat? Being a remote-first team, we’ve always put a lot of emphasis on getting together as an entire company once a year. In 2019, we all met up in Vail, Colorado, for a week filled with learning, team-bonding and maybe one too many local craft beers. We all left looking forward to next year’s retreat, where we’d get to see each other in person again… or so we thought.

Then the global pandemic hit and forced us to rethink the way we gather. We’ve even had to rethink why we gather as a team once a year. 

Our virtual retreat planning process

We originally had five days blocked off for our retreat, since that’s what we’d done in the past, but realized we were trying to force what worked in person, to also work online. When I started planning the virtual retreat, I gathered and read all the feedback I had received from the smaller virtual team retreats I had organized throughout the past six months, to get a good sense of what people did and did not like in a virtual environment. 

It was obvious people were really craving one-on-one interaction with their teammates. It was also obvious that people did not enjoy sitting through hours and hours of presentations. With this in mind, we decided on fitting all of our objectives into a half day. 

I knew I wanted to use the tool Icebreaker to randomly pair everyone off to have a guided conversation with team members they’d likely never spoken to before. Since I am a big believer in the saying “work hard, play hard” I also knew I wanted to provide a few activities that folks could choose from so they could have a little fun with their co-workers. 

One of the biggest challenges I had in planning this, was trying to find a time that would work with everyone’s time zones. Since we’re a global team, I knew this would be impossible without offering two activity timeslots. I decided on a 7 am PST activity time slot that anyone in Europe, on the East Coast and South America could attend, with the second activity starting at 12 pm PST, where everyone in the Central or Western states and New Zealanders could attend. 

Activities for virtual retreats

The activities we offered were a virtual cooking class with a private chef where we learned to make gnocchi and chocolate truffles. We also provided everyone with a stipend for ingredients. The second activity we offered was a tarot card reading class, which I found on Airbnb experiences. Lastly, we offered a game called Settlers of Catan, for anyone with a bit of a competitive nature. 

Once the first groups’ Icebreaker room and activity wrapped up, we jumped into the meat of the day. Starting at 8:30 am PST, we officially kicked off the retreat with short presentations from our CEO and COO. They went over some of the major team achievements of the past year and some of what we have to look forward to come in 2021. We then played a video we had produced just a few days before the retreat to help the team feel inspired and connected.

We followed that up with an awards ceremony to recognize some of our colleagues who really exemplified our core values this year. Each department had three winners who each won a really cool trophy and a $1000 cash bonus. 

We gave everyone a short break after the awards ceremony and also offered a stipend to order in a meal of their choice. We concluded the retreat with two 30-minute presentations from a merchant who uses ReCharge and a ReCharge agency partner who sets his clients up on our platform, both integral parts of our company’s growth. It’s so easy to get caught up in our day-to-day bubble and it was refreshing hearing how ReCharge impacts the users of our product. 

The folks who had not yet participated in an activity stayed online for their Icebreaker room and chosen activity. We scheduled it so everyone would have their afternoon off to relax and treat themselves for a job well done this year. As an extra token of appreciation to all the staff, we gave them a $150 gift card to spend on our swag store. 

As soon as the retreat concluded, we asked everyone to fill out a feedback survey. It was a near-even split between all 200+ employees on what their favorite part of the retreat was, which makes me feel like we really nailed it with having something for everyone. 

Top five tips to plan a virtual retreat

Here are my top five takeaways I learned from planning virtual retreats: 

  1. Keep the content short and digestible

    It is very difficult for people to focus for more than an hour over Zoom. Remember, you’re organizing a virtual retreat, not trying to replicate an in-person retreat for remote employees. 
  2. Give adequate breaks

    People need time to get up and get a drink or use the restroom without breaking their concentration. Offering short and frequent breaks tends to work best. However, people do want time to either make or order food and eat, so be sure to give some time for a meal as well! 
  3. Over-communicate your retreat date and agenda

    There will inevitably be some people who are offline when you make announcements, so the more communication channels you can announce the information in, the better! 
  4. Have an FAQ ready

    I suggest turning to a trusted colleague to ask them anything they might not understand after reviewing the retreat agenda/information. This can help you build an FAQ that will hopefully prevent dozens of people from messaging you with the same question.  
  5. Make it fun!

    This is really a time to celebrate coming together, whether as a department or a company-wide retreat. Reward your team with some fun team-bonding activities. This will help colleagues be able to connect on a deeper level and people also appreciate having a bit of a break from focusing on heavy content all day.  

While the retreat was overall a smashing success, I think we’re all very much looking forward to (hopefully) seeing each other in person again in 2021!!! 

Special thanks to our friends at ReCharge Payments for their insights on this topic.
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