Three Double Edged Swords of Virtual Retreats: How to Make Them Work for Your Team

Virtual retreats can actually be BETTER than in person retreats.

A few weeks ago, we talked about the perils of video conference fatigue and the ways that supplanting calls with videos can shift relationships for the worse. While days upon days with non-stop video calls isn’t leading to better connection or workplace relationships, there are some ways that video conferencing can actually improve experiences.

Even as Zoom and FaceTime have been a disappointing alternative to being in person, they have also made it possible for us to celebrate significant life events with people who otherwise could not attend; in the last year, I officiated a wedding via Zoom, while my co-founder celebrated his fortieth birthday with friends from all over the country — guests of both easily attended when days of travel weren’t requisite.

In a similar vein, I attended a twenty-year class reunion in which I got to hear from everyone present rather than having to figure out how to circulate among people and pull off seventy independent conversations before some uncreative bar manager turned up Semisonic’s Closing Time. On one hand, not being in person felt like a major bummer that robbed us of the rites and rituals we so enjoy. But on the other, it enabled a whole new dimension of connection that wasn’t available to us before. For one thing, video conferencing lets us control our own space and select more expansive playlists. It also lets us do so much more.

Cueing from these special personal experiences, our team has been designing and facilitating virtual retreats for our clients that focus on leveraging the best of what video technology has to offer while also designing around its shortcomings. Over the last year, we have designed and facilitated events with 12 to 35 participants, ranging from top executives to entire companies, for organizations as diverse as tech startups, community college systems, and large national nonprofits.

Our retreats have been far more successful than we imagined they could be, and our lessons from the experience have taught us that there are three “double-edged swords” of the virtual retreat.

Sword 1: It Happens by Computer

Pro: Everyone can see everyone, and we can control focus on the things that we really want people to be thinking or talking about. Whereas in-person events have to manage numerous spatial considerations, people coming and going, and the constant pull of other work, a video conference can be a compelling, attention-keeping way to get everyone working on the same thing.

Con: Video conference requires people to be on their computers, which are necessarily connected to the internet, and are also a primary portal for work. It’s so easy to toggle between video and email, and from taking notes to sidebar chatting with one another. It’s also easy to appear to be attending a large group video meeting while actually doing one’s taxes.

Solution: Work with the computer, not against. We use a shared “notetaker” — something we pre-populate with every person’s name for each session. We ask people to use the notetaker to record their thoughts in a way that is public and requires attention for participation.

We also recognize that people’s attention doesn’t magically expand when the retreat starts, so we borrow from the Pomodoro technique, which posits that most adults can focus for about 25 minutes before they need a break. We make sure that activities in our sessions shift in some way at least once every 20–30 minutes and give people real breaks hourly.

Sword 2: There is No Mingling

Pro: This may seem like an unequivocal “con” unless you are a person who finds mingling exhausting or anxiety-producing, but the fact that people will leave the retreat and not have to see each other in the hallways or lobby bar or out on the town has a major upside: it’s easier to have hard conversations. People can have difficult conversations without the danger of wrecking the entire day or worrying about how awkward it might be later.

Con: People won’t have a chance to deepen interpersonal connections in the same way they might if they could all take a cooking class together or invite one another to chat over a nightcap. That means these experiences need to be choreographed.

Solution: Work with the technology. Use breakout rooms to enable people to connect 1:1, or in small groups, with the explicit expectation of achieving an outcome. Open the chat feature and encourage people to use it liberally for color commentary that can be shared with the whole group. Teach people how to raise hard things in the right moments and leverage great facilitators to help work through impediments to progress.

Sword 3: People are on Video Conference All. Day. Long.

Pro: Bear with me. With due apologies to KRNV and the people of Reno, my very first appearance in front of a news camera was nothing short of a catastrophe (every PR person’s nightmare, really), but it also taught me a lot and getting used to being in front of a camera has made an enormous difference since. A slight variation on the Hawthorne Effect, awareness of being on camera can alter behavior. Getting used to it (or “attenuating”) can mitigate such self policing, and that is helpful when the objective is to develop stronger human connections.

Con: Being on video all day is exhausting (for a variety of reasons well cataloged elsewhere) and people come to both resent it and take it for granted.

Solution: Begin with something atypical. Our icebreakers range from asking participants to explain their most listened to album from the top 50 of Rolling Stone’s 500 Greatest Albums of All Time to completing a 30-minute competitive group Kahoot! Quiz about their colleagues’s predilections. They work and are always worth it. Take the time to plan very thoroughly. Our clients hire us to prepare and facilitate their retreats because we develop to-the-minute agendas and session guides, focus on ensuring that all of the time we ask of people is devoted to a specific outcome, and deeply informed by a cross-section of participants. It takes us about three hours of preparation for every one hour of retreat.

Participants have reported that our retreats are besting even their most favored in-person predecessors. But as my most-admired TV icon, LaVar Burton would say, you don’t have to take my word for it. Here’s what participants have said:

• “Every activity/session felt purposeful and there wasn’t any wasted time. It was even better than the mid-year in July, which was hard to top!”
• “Well organized, ran super smoothly, provided meaningful interactions and opportunities to come together on personal and professional levels as a team, and I feel like we came out of the retreat better knowing our vision moving forward.”
• “It was a great remote retreat! Really facilitated connection and thoughtful consideration of the future path for the company as a whole and individual roles in that.”
• “I was engaged throughout the two days, benefited from the conversations with colleagues and appreciated the structure of those discussions.”

Virtual retreats don’t have to be an exhausting slog that distract from getting real work done. On the contrary, they can be enormously effective tools for collaboration and connection. One last suggestion, though: don’t let the momentum end after the lights go down on the last session. Follow up with a participant survey on personal commitments to next steps, and make sure to compile and share a binder of everything developed and decided upon during your time together. It can serve as a powerful roadmap for the work to be done before your next great virtual retreat.