Running a Virtual Retreat
Prison Break Escape Game screenshot

Running a Virtual Retreat

Retreats are a great way for a team to get to know each other better and have a break from their work responsibilities. I’ve organized in-person and virtual retreats. In this article I'll be talking about how to run a virtual retreat using one I recently ran at Dutchie as an example. Here are some of the pros of running a virtual retreat:

  • Cost - For groups that are disbursed, especially if the company has no office, this can save money.
  • Safety - Zero chance of getting or spreading COVID-19 (and any other virus). One of the participants planned to decline if we were going to meet in person. It is critical to me that as many people in the team can attend as possible.?
  • Care Responsibilities - Many of us have eldercare and childcare responsibilities that make it difficult to attend an in-person retreat.
  • Accessibility - It’s easier to accommodate most accessibility needs.

There are also some cons you should consider:

  • Time-zones - Scheduling for teams that have people in multiple time-zones is a challenge.
  • Screen Fatigue - It can be stressful having your camera on and looking at faces on your screen even for social events.

Once you’ve decided to pursue a virtual retreat, I recommend polling the team about what they want to do, you might be surprised at their answers. A survey also reduces the chances of conformity pressure, thus creating a higher likelihood of honest answers. Here’s an example poll I made for the team at Dutchie:

Poll results for what to do

The top selection was cooking together. There was a three-way tie for the next spot with Virtual Escape Room, Ordering Food In, and Building Something Together. Due to a prior survey, I already knew the dietary needs of the team. We had multiple vegetarians, one vegan, and I am lactose intolerant. Based on those requirements I booked an AirBnB experience making corn tlacoyos, salsa, and vegan stew which cost $26 per person. I also had participants submit expense reports for up to $30 in ingredients, which came out of my department's quarterly budget. The AirBnB experience was building something (ie: food) together and involved food so I also booked virtual escape rooms. The amount of activities was also based on a question in the survey asking how long the event should be:

Poll results for how long the retreat should be.

The majority of people wanted a single day retreat with 33% of them wanting 2 - 4 hours and 33% wanting 5 - 8 hours. The team was too large for a single escape room so I booked Prison Break and Gold Rush at $40 per person, which was paid by the Engagement Team. Prison Break was rated harder, so I assigned the people more experienced with Escape Rooms to it.

The retreat's agenda

This was the final schedule for the retreat. We started with a brief overview of the plans for the day. The company's engagement team ran us through a few short icebreakers that made use of Zoom breakout rooms. We then had a short break prior to the escape room.?

The Escape Game staff gave us an intro for each room. Each room had a staff member with a camera on their head, so we could see what they saw. In my case, I was in the Prison Break escape room so the staff member was portraying a prisoner who we would help to escape. Our screen also showed an inventory of everything the prisoner picked up. Both teams beat their room.

After a break, we did the cooking together. It worked out so that the timing was synchronized to East Coast dinner and a little late for West Coast lunch. Not only did we learn some Aztec cooking, we learned about the geography and history of what is now Mexico. The teacher had a camera pointed at the cooking area and another pointed at her.

Corn Tlacoyas

We finished the day eating our creations. It also gave us a chance to talk about the day. Several of us were off camera for this part. If we were to cut a portion of the event it would have been this.

After the event I created a feedback survey. Overall people really enjoyed the event and getting to know each other. The survey showed we collectively had expected to enjoy the escape room more. While we did enjoy the Escape Room, we found the cooking to be even more fun. For weeks following the event it seemed clear to me that the team was in higher spirits and had a better sense of cohesion.?

Screenshot from the Gold Rush escape room team.

With a little bit of planning and money a virtual retreat can help you to improve morale and get people to know each other better. A virtual retreat can also be used to have work activities like an idea generation session, discussion of new OKRs, or anticipated changes to the team.


For more advice and ideas please message me on LinkedIn. This article is a sneak peak of a leadership book I’m working on.

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