How to plan & host a kickass virtual retreat

How to plan & host a kickass virtual retreat

Our team retreats were one of the things I’m most proud of as CEO and co-founder of Close. We put a ton of thought and effort into creating a retreat that brings our team together intellectually as well as socially.

We organized these physical remote company retreats every six months. We'd pick a place and then fly in team members from all over the world to meet, and they were an essential part of our company culture and planning.

Then 2020 hit.

We realized pretty quickly that our physical team retreat wasn’t going to happen. And that meant Mary, our head of people operations, and I would have to find a way to replace this incredible atmosphere of remote team building that we had created.

It took a lot of effort, but we were finally able to create a virtual team retreat that was valuable for everyone involved.

Today, we’re going to walk you through our process for creating a virtual team retreat that people actually enjoyed attending, as well as the lessons we learned before, during, and after.

2 main goals of our team retreats

For remote teams, getting together to discuss work and life essential for company culture. To start our process for building a virtual team retreat, we first had to dissect our goals for the event. What were we expecting the team to get out of this?

For both in-person retreats and virtual ones, we focus on two main goals.

The goal that most remote companies focus on is strengthening the social bonds of the team.

Remote teams do not have the advantage of seeing each other on a daily basis and developing relationships with their coworkers. This is why team retreats often have the goal of getting people to connect on a social level with different events and activities. Especially for individuals who work on different teams within a company, retreats are a time to build better communication, get to know each other, and strengthen social bonds throughout the company.

And while this is absolutely part of our retreats at Close, the social aspect is not our primary focus.

Our #1 goal for team retreats is business alignment.

We want everyone in the company to walk away from a retreat on the same page.

In previous retreats, we’ve focused on creating clarity. We discuss what’s been happening company-wide, brainstorm and align on what’s coming next, and bring one singular focus and priority to the team.

This encourages individual buy-in to new ideas and priorities, as well as encouraging ownership of these goals across the whole company.

By the end of a typical retreat, our entire company feels a common sense of mission, direction, and clarity on what’s coming.

But of course, accomplishing both of these goals in a remote setting presents its own unique challenges.

The challenges of hosting a virtual retreat

One thing was clear from the get-go of planning: We couldn’t keep our original in-person retreat schedule.

With 3 obvious challenges to overcome, it became clear that our virtual retreat had to be very different:

Time zones

At Close, our team is distributed over 9 different time zones.

When we started planning, Mary got busy calculating how much time we could reasonably overlap with each other.

The answer: 4 hours.

That meant that, if we wanted our global team to be online together at the same time, we could only plan events for our virtual retreat during a 4-hour period each day. (Otherwise, we ran the risk of team members on the West Coast showing up in their pajamas, or team members in Europe and Asia dozing off during presentations.)

Zoom fatigue

Because it’s a real thing.

Above, we talked about two clear goals that we had: To strengthen social bonds and have productive, meaningful conversations that aligned each individual to upcoming company goals.

People who have spent hours in Zoom meetings aren’t engaged and certainly aren’t in the mood to brainstorm with their teammates.

This retreat had to be valuable to each individual, so we needed to plan it in such a way that everyone was engaged during the time they spent online.

Non-focus environment

At an in-person retreat, everyone is together, focused on work, and bringing ideas and energy to the table. At a physical retreat, we would never think of having people sitting in front of their laptops while meeting together.

But that’s exactly what they had to do while attending a virtual retreat.

Each individual would be connecting from their homes, in front of a laptop. This is the worst environment to keep someone engaged and focused because they’re always just a click away from checking their email, answering a support ticket, coding a bit, or doing other work.

And of course, the normal ‘distractions’ of WFH life would still be there, such as family, pets, household chores, and incessant Amazon deliveries.

Despite the challenges of gathering a distributed team for a live online event, our virtual retreat turned out to be a huge success.

So, how did we do it?

How we overcame the challenges and built an engaging virtual retreat

From the very start of planning, I set this standard: Every moment had to be high-engagement for the whole team.

If even a second of this virtual retreat was not highly-engaging to every member of the team, I knew we’d start to lose people.

We didn’t want people to start thinking of this as optional, or something they could’ve just watched later. Every person should look back at the virtual retreat and think that it couldn’t have been done any other way than live.

This wasn’t just us pretending to do a retreat when it’s not the ‘real thing’ that we’ve built in the past. This was a completely new event and experience.

To that end, we focused on building highly-engaging moments that the whole team would share and enjoy.

Every idea we had was dissected and measured against the goal of being engaging, and many of our ideas were cut because of this high standard.

This is what our team had to say about the results:

It is possible to build almost the same synergy we do when we’re together in a team retreat. I haven’t felt so close to the team for a while! Of course, team retreats are still the best, but I was really impressed and surprised with how good this summit was.
We’re in this together. Lots of excitement for what’s coming!
I now have better insight into what other teams are working on and have a clearer picture of what our company goals are. I feel more aligned with the whole team.

So, how did this virtual retreat look in practice?

Our virtual team retreat schedule

Our pre-COVID, in-person retreats are week-long events where teams are working together, presenting ideas, brainstorming, and doing fun social activities together.

How would we bring this same spirit to a virtual retreat with a team distributed across 9 time zones? In the end, we planned 2 days of main events, with some other supplementary activities during the week.

Check out our virtual retreat schedule:

Tuesday: Kickoff event

In lieu of our weekly all-hands meeting, we held the kickoff event of our virtual retreat: a fun social event.

We went through plenty of ideas for social activities we could use to get the team laughing and having fun. In the end, we settled on TeamBuilding, a great company that hosts all kinds of fun remote team building activities.

This team-building activity was optional, but almost all of our team attended. This worked best for us because there was someone outside the team hosting the event, making it different from the regular meetings we have where either I or Mary host. Plus, the host from TeamBuilding was loud, high-energy, and kept everyone involved throughout the activity. (If you're looking for inspiration, they have a list of free virtual activities you can try with your team.)

This was a great way to kick off our virtual retreat and get everyone laughing and comfortable.

Wednesday: Presentations

This was Day 1 of our main event, and it was planned to bring that business-alignment we spoke about before.

Here’s how it went:

State of the Union

My State of the Union presentation is a standard event at our in-person retreats, and it made sense to add this here as well.

This presentation introduces the sentence or phrase that will be the theme of our retreat. I also take some time to look back at where we’ve come from and where we’re going as a company.

This presentation allows all the individuals on the team to be aligned with what we’re trying to accomplish as a company.

Marketing and Product presentations

Normally, each team gives a presentation about their recent accomplishments and upcoming projects at our team retreat.

But with the time constraints we had in place, we realized it wouldn’t make sense to have all the presentations as we normally do.

Instead, we focused on the two teams who had the biggest change in messaging and direction and allowed them to give updates to the rest of the team. In our case, this was the Marketing and Product teams.

Each team leader gave a presentation about the current state of the department and the roadmap for upcoming months into 2021.

Brainstorming Sessions

When a team is together physically, brainstorming and discussions about work happen more naturally.

Could we rely on our team to take to Slack to discuss ideas after the presentations? Knowing them, they probably would’ve done it, but we wanted to facilitate this brainstorming among different teams as much as possible.

So, after both the Marketing and the Product presentations, we created breakout rooms in Zoom so that the members of different teams could get together and discuss ideas and questions about the presentation.

In one of these breakout sessions, Mary organized the groups so that members of all the teams would be mixed together to discuss and brainstorm across different topics. That way, individuals had the opportunity to ask questions in real-time and digest the presentations they had seen alongside team members that they normally wouldn’t have the chance to speak to about these topics.

At the end of the retreat, this was the moment that everyone kept referring back to. Here’s what some of our team members said about the structured brainstorming sessions:

Having a QA right after the presentation is a great idea. Specifically, after the product presentation, I felt very energized and ready to discuss stuff.
Loved the smaller breakouts following each session to discuss takeaways. I think it generated a lot of discussions that normally happen at dinners or over drinks at team retreats. Would like to see these transition into the in-person retreats as well (whenever that's a thing again).
I'd say the group discussion after the Marketing/Product presentation was most valuable to me. It's nice to hear other people's thoughts, concerns, etc. I feel we could have more brainstorms like these!

New-hire and co-founder virtual coffee meetup

Our physical retreats usually include a dinner for any new hires that came on since the last retreat to get to know the company founders.

With this new setup, we created a virtual coffee meet-up so that we as the founders could get to know all the new hires that came on this year.

Day 1 review

With the first day of our virtual retreat come to a close, the organizers of the event took some time to recap and prepare for Day 2.

Myself, Mary, and one of the other co-founders set up a small summit check-in at the end of Day 1. We talked about what had gone smoothly, what needed to change, and what we needed to prepare for the next day.

Thursday: Customer interviews and social events

Day 2 dawned bright and early (for the people on the West Coast, anyway).

Customer interviews

Our customers are always the main focus here at Close, so customer interviews are a regular part of our in-person retreats.

In a virtual setting, we decided to keep the structure of these calls similar to what we would normally do. We asked some of our customers to talk to smaller groups of our team members, and assigned each team member a live interview to join via Zoom.

A member of the customer success team led these discussions, first explaining to the group who this customer was, and then going through the interview with pre-prepared questions that helped the team understand more about the customers that work with us and how they use our product.

At the end of the interview, the team had a chance to ask the customer questions, and later the groups would have a chat about what they’d learned.

Milestone celebration

Let’s get this out in the open: We are celebration noobs.

But we reached a huge milestone as a company and wanted to celebrate with the team!

So the question was: How can we celebrate simultaneously with people across the globe?

First, there was a presentation. Mary went back in time and collected some pictures that described our timeline as a company, from the beginning of Close to where we’ve grown to now.

Second, to make this a real celebration, there had to be cake. (Obviously.)

So we actually ordered mini-cakes for our entire, international team. While it was a bit harrowing trying to get them across borders and through customs, we can happily report that (almost) all the cakes made it in time for our celebration.

To make this celebration even more fun and engaging, we decided to turn our company timeline into a fun trivia game. We used Mentimeter to create a trivia that our team members could access from home, and quizzed them on the history of Close.

This session was designed to spread that sense of accomplishment over what we’ve built at Close, and it certainly achieved that goal.

Wrap up and Q&A session

Before and during the retreat, Mary gathered questions from our team members around the world.

Q&A sessions are an important part of our physical retreats, as they give individuals access to me directly as the CEO of Close. For our virtual retreat, this was no different.

At the end of the retreat, as a way to wrap up, I led a positive discussion and answered as many of these questions as I could.

Optional remote work session

Our third and final ‘social’ event of the virtual retreat was an optional session around remote work in 2020.

We understand that many of Close’s employees have faced challenges this year due to COVID-19, so we offered them a space to come together and have an open discussion about how different this year has been for remote workers and how they’ve overcome the challenges. We've always believed that supporting employees in times of crisis is a fundamental part of building a strong company culture.

Friday: Day off

As our final gift of the week, everyone had Friday off.

And it’s no surprise that people loved this part.

Giving a free day was really appreciated and that's also something that Close is really good at: putting people before the business.

Having Friday free also helped those whose location made the virtual retreat a bit more inconvenient due to the time difference.

One week later: Reviewing how we did

Directly after the last session ended on Friday, Mary sent out a feedback survey to the team.

Each individual was invited to express their thoughts and opinions about this virtual retreat, as well as the ideas they had for the next one. While some team members sent direct messages to Mary, there was also a form they could fill out anonymously and give their real, unfiltered thoughts on how things went.

The week after the retreat, the founders got together and talked about how things went, reviewing the feedback that the team had sent. At our next directors meeting, the team leaders also shared with us what they had heard from their team.

All-in-all, this structure served as a way of uniting a disparate team across 9 time zones, gathering ideas, and building a foundation to move forward in the same direction.

How to plan your own virtual retreat: 5 lessons we learned

For a team that is very accustomed to meeting in-person and all the high-energy fun that entails, this virtual retreat was clearly very different.

But in the process, we learned some important lessons about building a virtual retreat that people actually enjoy attending:

1. Edit down

Something we realized early on in the planning stages is that long, uninterrupted periods of presentations and meetings would not engage the team.

Besides the presentations we would normally have in a physical retreat, we were also gathering tons of ideas on activities and games to include.

Obviously, there was too much content, and trying to cram all of these things into a short period in a remote setting would’ve been a disaster.

So, we learned to edit down. In a virtual setting, whatever presentations or meetings were not absolute must-haves got cut.

The result was a fully-focused 2-day summit that brought our team together in a fun, productive way.

2. Frame the expectations

Our previous team retreats were pretty spectacular.

Because these retreats were so special and important, the word ‘retreat’ carries unique meaning for our team. That word conjures up this incredible atmosphere that we always promoted.

And when planning our virtual retreat, we realized it wasn’t going to be the same. Because Zoom just isn’t the same as in-person, no matter how excellent your virtual background is.

This is why, instead of calling this a retreat, we called it the Q4 Team Summit.

By changing the name of the event itself, we sent a clear message to the team that this was going to be different. We had the same goals, but the team was prepared for a completely different experience.

Remote teams need to find a way to frame their virtual retreats and set correct expectations within their team.

For us, this also meant encouraging our team to speak up about what they liked or disliked about the summit. We made it clear: This is our V1, and we’re looking to improve.

3. Plan your schedule thoughtfully

Many remote teams have workers in various time zones. This is one important lesson we learned: You must adapt your virtual retreat to the time zones and necessities of your team.

For our distributed team, that meant planning a virtual event that took place within a specific 4-hour period of the day. For other teams, you may have more flexibility with the hours involved. Or, for more distributed teams, you may need to mix live sessions with asynchronous activities. (Check out this roundup post from Remotive to see how other remote teams planned their virtual retreats thoughtfully.)

Thoughtful planning also involves scheduling time for breaks in between sessions and being more flexible to people’s at-home lives. (In other words, if someone wants to grab a bite during a presentation, let them!)

4. Review the cadence

Every remote company plans its retreats differently. But whether you plan your retreats annually, bi-annually, or quarterly, it’s time to rethink that cadence once again.

Another reason we changed the name of our retreat to Q4 Summit was that we foresaw this becoming a quarterly event going into 2021.

For your remote team, think about whether it makes sense to increase the frequency of these team-wide events. With a more compact format and time constraints, it may make sense to hold virtual retreats more often than you would a physical retreat.

5. Keep it simple

When Mary and I first started brainstorming how we would do this virtual retreat, there were so many different ideas that came to mind. From different activities, events, games, to different formats or even platforms, there was a lot to discuss and decide.

In the end, we went for the road of least friction, using the same tool we use every day for meetings: Zoom.

For remote companies looking to host their first virtual retreat, it can be exciting to discover the endless possibilities available. But our advice to you is to avoid going overboard, especially for your first time.

Focus on getting the program right, building a schedule that keeps your team engaged, and coming away from the retreat feeling energized and ready to dive back into work.

Maintaining that connecting after your remote retreat

When everything was said and done, it felt good to receive feedback like this from our team:

Well done! Streamlined and to the point.
I can't see anything that wasn't valuable enough.
I like that it was compact, short, and gave us a lot of time to work on our daily responsibilities.
Thank you very much for organizing. Felt like the perfect number of meetings spread over the perfect amount of time.

But even though this event was a success, we knew that it wasn’t the end of the road.

Actually, we’re still just getting started.

Remote team building isn’t something you do once and forget about. This is a process you must build consistently.

Here at Close, we live by the mantra, “Build a house you want to live in.” And it’s what we encourage other remote companies to do as well.

Continue to work at building a remote team culture that everyone enjoys and feels comfortable in. Maintain a positive atmosphere, and help your team continue to develop the connections they built at your virtual retreat.

Keep pushing to improve, and your team will keep pushing to give you their best in return.

Want to plan your own virtual team retreat? Here's a free checklist that'll make things way easier!