How to Host a Virtual Retreat

Are you looking to plan a virtual retreat for your company but don’t know where to start? We’ll share our own tips and tricks so your virtual retreat can be a success too.

It was a sad day when we decided to cancel our beloved YNAB team retreat in 2020. (COVID!). Our company has been fully remote since its start, and those once-a-year in-person retreats have been legendary, after all! But with purposeful planning, we pulled off a virtual retreat that still captured the magic.

Our retreat happened over two weekdays, six hours each day, including breaks. Here are some activities we included, along with tips and lessons learned to inspire your own!

How We Ran a Successful Virtual Retreat

Build the Excitement

About a month before the retreat, we created a designated retreat Slack channel to build excitement, and get good chatter going. Anticipation is key! We threw out teasers about swag coming, board games, and other things our team gets jazzed about.

Bring the Magic with Snacks

Snacks are a non-negotiable part of our in-person retreats! So, to still include them, we used SnackMagic, a snack-gifting platform. About a week before the retreat, everyone received an email from SnackMagic treating them to a box full of snacks they could choose.The boxes arrived just before the retreat, and wow, you would have thought we surprised the team with a trip to Maui!! (Editor’s note: this is no exaggeration. They were awesome.)

You Can’t Go Wrong With Meal Delivery Gift Cards

Eating meals together is also a much-loved part of in-person retreats at YNAB. We sent every team member an e-gift card to a food delivery service (whatever they had locally) so that people could still eat “together” if they wanted to.

Play Online Games (And Test Them First)

Board games are an absolute must at YNAB retreats! (Maybe the #1 must-have.) Our Operations Team tried out some online games ahead of time, (hey, someone had to do it!), then we asked the team to sign up for the game(s) they wanted to play each day. Before and during the retreat, we made sure everyone knew where to be for each game, who their group leader was, and even sent calendar invites that included the group info and game links. Codenames and Drawphone were both big hits!

Plan Some Fun, Unexpected Activities

We included some other fun, unexpected activities that helped people meet in smaller groups and get to know each other. We used Puzzle Break for a virtual escape room (loved this!), Icebreaker for randomly assigned one-on-one chats, and a for-fun work project that we titled the Small Teams Super Secret Work Project. We kept the details for that one, well, secret, until the project started!

Try Hometown Tours

Team members could each choose to create an optional video showing us their home or hometown. We watched these Hometown Tours together for 30-minute chunks a few times throughout the retreat. We loved getting these glimpses into each other’s homes and neighborhoods!

8 Do’s of a Virtual Retreat

1. Be clear about the agenda. Are there certain activities that everyone on the team will want to attend? What is optional?
2. Be sensitive to the fact that people will be attending from home. They will have needs and interruptions (hello, hungry toddler!) that wouldn’t be there if the retreat was in person. Let your group know it’s okay to be flexible with their schedule when needed!
3. Leave a little mystery! Plan some surprises or activities without showing all your cards.
4. Give opportunities for people to interact one-on-one or in small groups. As much as possible, recreate the impromptu chats that happen in person, when people really get to know each other.
5. Give food in some way!! Many people relate over food. But if food isn’t your team’s thing, find something else that does build connections on your team, and incorporate it.
6. Communicate, communicate, communicate. Let your group know dates, timelines, and (at least) tentative plans in advance, and then make sure everyone knows where to go at any given time. We had a master agenda (Google doc), and posted Zoom meeting links and reminders in Slack throughout the retreat.
7. Know your team! Do they need a whole week for a retreat? What sparks conversations? What helps them connect? What past activities have they talked about long after they happened? What inside jokes come up often?
8. Walk through the entire retreat as if you were a team member. What questions could come up for someone at certain points? Adjust your schedule, instructions, and plans so that it is as stress-free as possible for your team. Help it flow for them.

3 Things to Avoid During a Virtual Retreat

1. Doing too many activities. There are a lot of fun options for virtual retreats, but resist the urge to do them all. Choose those that fit your team best! Think quality over quantity.
2. Throwing something together. Even a virtual retreat requires a lot of careful planning, or it will feel like another cheesy conference. Don’t just hold a retreat for a retreat’s sake.
3. Thinking that it will be perfect. Do your best to plan and obsess about details, but then roll with the punches when something doesn’t quite go as planned.

What Else We Learned

• Build in real breaks. Consider including times during the retreat hours that are true breaks, when there isn’t anything going on. That way people don’t have to choose between “optional” activities or really giving themselves a break from the socialness of the retreat. It helps decrease FOMO. 🙂
• Be sensitive to team members in different time zones. This time, we kept our activities to standard work hours for most of the team. But since we have a large handful of international team members too, next time we will schedule more activities during their standard work hours.
• Leave space between activities. People want time to just chat and catch up, separate from playing a game together or doing another activity. They need opportunities for unplanned conversations and interactions. Next time, we might leave a little more breathing room between activities.

With any retreat, virtual or not, the most important part is the people. Your team. So whatever you choose to do for your virtual retreat, keep your people front of mind, and have fun with it. If you aim to delight them, and show them how valued they are, you can be prrreeeetty certain you’ll nail it!

Want to learn more about YNAB’s company culture or how to thrive as a remote workforce? Follow us on LinkedIn or tune in to our founder’s weekly podcast!