The Virtual Retreat Guide: How to Plan an Engaging Retreat for Your Team

Our team retreats are one of the things I’m most proud of as CEO and co-founder of Close.

Mary, our Head of People Operations, and I work really hard to organize them every six months—and we go all out. We pick a cool location. We fly in all of our team members from around the globe. We also build up our company culture while strategizing for the future.

2020 put a screeching halt to our plans.

We quickly realized that we couldn't host a typical corporate retreat. But we weren't willing to abandon our incredible remote team-building events either.

So, we created a virtual experience instead.

I won't lie; it took a ton of effort. However, we figured out how to create a virtual team retreat that was still valuable to everyone involved. And we've learned even more about the process since then.

So, today, I'm going to share how Close does remote shindigs—ones that our employees actually enjoy attending and help us achieve big-time company goals.

The Challenges of Hosting a Virtual Retreat

One thing was clear from the start: we couldn’t keep our original in-person retreat schedule. Why? Because we had three obvious challenges to overcome:

Time Zones

At Close, our team is distributed across nine different time zones.

Once the virtual retreat planning process began, Mary calculated the amount of time we could reasonably overlap with each other. The answer was just four hours.

In other words, to ensure our global team was online at the same time, we had to host our virtual retreat during a four-hour window every day. If we didn't, our West Coast staffers would show up in their pajamas while our European and Asian staffers dozed off in their chairs.

Zoom Fatigue

Because it’s a real thing.

Generally speaking, people who've just spent hours in Zoom meetings don't want to engage and brainstorm with their teammates. But these things were key to our retreat's success.

To make sure the online event was valuable to every individual, we needed to plan it in a way that allowed everyone to fully engage when they joined us online.

Non-Focus Environment

In-person retreats bring people together to focus on work and swap ideas. There's a natural energy there that keeps people engaged. That same energy doesn't exist with online retreats.

Team members usually connect from their home offices. It's not a terribly engaging environment—especially when typical work-related tasks are just a click away. And I haven't mentioned the normal distractions of WFH life, like family, pets, and Amazon deliveries.

We needed to overcome this obstacle to ensure the success of our virtual retreat. I'm happy to say we were able to do it. In the next section, I'll share our schedule to pull it off.

Virtual Team Retreat Schedule Example

Our traditional in-person retreats last for a week and aim to foster teamwork and brainstorming sessions while enabling our employees to participate in fun activities.

Is it possible to plan something similar over the Internet? To be honest, probably not. But we did find a way to make our virtual get-together valuable. This is what it looked like. Feel free to use our schedule as a template for your own online gatherings.

Tuesday: Kickoff Event

We kicked off our virtual event with a social gathering.

The goal was to get our whole team laughing and having fun. To help make that happen, we partnered with TeamBuilding, a great company that hosts virtual team-building activities.

Our kickoff event was effective, in part, because it was hosted by a third party, which differentiated it from our normal company meetings. Plus, the host from TeamBuilding was high-energy and super engaging. This made the icebreaker activities extra fun.

Wednesday: Presentations

Wednesday was the first full day of our event, and we had one goal: increase business alignment. We achieved this via a series of virtual presentations.

State of the Union

I always give a State of the Union presentation at our in-person retreats. There was no reason to exclude it from our virtual event schedule, so I went for it.

The goal? To introduce the theme of the retreat, reflect on how far our company has come, and discuss where we'll go in the future. Sharing this kind of information helps every team member understand organizational goals and align with them.

Marketing and Product Presentations

I ask every team to present at in-person retreats. It's a great way for them to educate their co-workers on their processes, accomplishments, and future goals.

But, our virtual event had serious time restraints, as I already mentioned. So we focused on two specific teams, each of which had experienced major changes since our last gathering.

Those two teams were Marketing and Product. The leaders of each department spoke to the rest of the company, touching on their current state of affairs and upcoming plans.

Brainstorming Sessions

When teams share a physical space, work-related brainstorming sessions happen naturally.

It's really difficult to create the same atmosphere via Slack. I know our employees would have tried, but we wanted to find easier ways to facilitate brainstorming across different teams.

So we created multiple Zoom breakout rooms, which our employees could use to meet with each other, ask questions about the Marketing and Product presentations they'd just attended, and otherwise discuss important Close topics face-to-face in a smaller setting.

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New-Hire and Co-Founder Virtual Coffee Meetup

Our physical retreats usually include a special dinner—just for new hires. It's a great way for them to meet the founders of Close, myself included. We didn't want to completely abandon this element of the event because we'd gone virtual. So we created an online coffee meetup instead, that allowed the founders to get to know new hires on a more personal level.

Day One Review

At the end of day one, Mary, one of the other co-founders, and I took time to evaluate. What went right? What went wrong? What did we need to prepare for day two? This helped us refocus on the next stage of our virtual retreat and ensure it was valuable for our employees.

Thursday: Customer Interviews and Social Events

We started day two bright and early (for our people on the West Coast, anyway.)

Customer Interviews

Our customers are the heart of everything we do at Close. That's why we've always ensured customer interviews are part of our in-person retreats.

Fortunately, we didn't have to change much to add them to our virtual get-together.

We simply asked a few customers to answer pre-prepared questions via Zoom. Each of these interviews was led by a member of our Customer Success team and helped our employees understand how our product is used. At the end of each interview, employees asked the customer questions and then broke off from the large group to chat about what they learned.

Milestone Celebration

Let’s get this out in the open: we're celebration noobs.

However, our company reached a huge milestone during our virtual retreat, and we wanted to celebrate. The only question was, how do we ensure everyone can participate?

We started with a presentation. Mary collected pictures that illustrated our timeline as a company, from the beginning of Close to where we are now. Then we ate cake.

No, we didn't ask our employees to buy themselves cakes from their local supermarkets. We ordered mini cakes for each of them, then smuggled them through customs and across borders so we could all celebrate in style. (Just kidding. We obeyed every law and regulation and still managed to ship cakes to just about every team member in time for the big party.)

But we weren't done yet. To make our celebration even more fun and engaging, we turned our company timeline into a trivia game with Mentimeter, which team members could play from home. This helped our whole company enjoy the success we've achieved together.

Wrap Up and Q&A Session

Q&A sessions are an important part of our physical retreats, as they give individuals direct access to me, the CEO of Close. This was also true of our online retreat.

Mary gathered all of the questions our team had for me, both before and during our retreat. Then, as a way to wrap up the event, I answered as many of them as I could.

Optional Remote Work Session

Our third and final "social" event of the retreat was a session about offsite work in 2020.

We understood that many of our employees faced challenges due to the pandemic. So we offered them space to come together and have wellness discussions. We've always believed that supporting employees in times of crisis is crucial to building a strong company culture.

Friday: Day Off

We wanted to end our virtual retreat with a bang. So we gave our entire company the day off on Friday. As you can imagine, our team loved this part of the event. Seriously, we received numerous notes about how much our employees appreciated the extra time to recharge.

How to Plan Your Own Virtual Retreat: 7 Lessons We Learned

Our team was very accustomed to meeting in-person—and enjoying all of the benefits associated with face-to-face get-togethers. Our virtual staff retreat was clearly different.

But in the process of planning and hosting it, we learned a bunch of important lessons about how to build a retreat that people actually enjoy attending:

1. Edit Down

Lengthy online presentations and virtual meetings don't engage people.

Do your best to streamline online content. And, if possible, break up long sessions with virtual retreat activities, such as a fun award show, escape game, or digital scavenger hunt.

This can be hard to do—especially when you're used to hosting in-person events. To make it easier, ask yourself, "Is this speech or presentation totally necessary?" If the answer is no, consider cutting it from your virtual retreat schedule to create a more focused gathering.

2. Frame Employee Expectations

Like I said, Close's previous team retreats were pretty spectacular.

Because of this, the word "retreat" has a unique meaning among our team members. People automatically think about the incredible get-togethers we planned and promoted in the past.

We knew right away that we wouldn't be able to capture the same magic in a virtual setting. That doesn't mean online retreats can't be tons of fun and super valuable. But we knew that we had to reframe our team's expectations before they joined us online.

To help smooth out the reframing process, we called our event the "Q4 Team Summit." This sent a clear message to our team that the event we planned was different than in the past.

Whatever you do, make sure your employees know what to expect from your virtual retreats. That way, they don't conjure up images in their heads that you could never create in real life.

3. Plan Your Schedule Thoughtfully

If your company employs people in different time zones, you need to adapt your virtual retreats to accommodate their needs. Team members shouldn't have to attend sessions at 8 pm on Sunday nights, for example, so others can attend at 9 am on Monday morning.

For us, that meant planning sessions within a specific 4-hour period of the day. Your team might have more flexibility, especially if all of your remote workers hail from the same country.

Or maybe your team has even less flexibility than we did. If that's the case, you may need to mix live sessions with asynchronous activities. (Check out this post for more ideas on that front.)

One more thing: thoughtful planning requires you to schedule break time between sessions, and to give your employees more freedom than they would have at in-person events. (In other words, if someone wants to grab a bite to eat during a presentation, let them.)

4. Review Your Event Cadence

Every company plans its retreats differently. Whether you host annual, bi-annual, or quarterly get-togethers, I encourage you to reassess your current cadence.

One of the reasons we changed the name of our retreat to "Q4 Summit" was that we wanted to start hosting quarterly events in the following year. Do you want to do the same?

Ask yourself if it makes sense to increase the frequency of your company-wide shindigs. By cutting back on content, as mentioned above, and hosting virtual gatherings instead of in-person ones, you can host awesome retreats without the typical financial repercussions.

5. Keep It Simple

If your team is anything like mine, you have tons of virtual retreat ideas you'd like to implement. You need to host A, B, and C sessions. And wouldn't it be awesome to plan X, Y, and Z activities? Maybe you could get a few guest speakers to show up, too…

At the end of the day, simplification is your best friend. Choose the path of least resistance. That way, you can focus on delivering true value to your team.

For Close, that meant using the same video conferencing tool we use every day: Zoom. It's not the fastest solution, but it's familiar. We didn't want our team to worry about the online platform we used to host our virtual company retreat. We wanted them to enjoy themselves.

‎So, while it may be incredibly tempting to "go all out," try to avoid this impulse. Your virtual retreat will be less stressful. It will probably be more beneficial to attendees, too.

(Note: this not a license to skimp on your employee get-togethers. They need to be amazing. But focus on quality content, a realistic schedule, and attendee engagement. Everything else is a distraction that you should limit if at all possible.)

6. Set Clear Goals for Your Retreat

What do you want your virtual retreat to accomplish?

Close retreats have two goals: to create business alignment and to strengthen the social connections between team members—team members who hardly ever get to see each other in person. Every session, activity, etc., is designed to help us achieve these things.

The goals of your online retreats might be different. Maybe you want to teach your employees new skills, help them relax, and rejuvenate them when they return to their normal work schedules. Maybe it's something else entirely.

It doesn't really matter as long as you know what your goals are before you start planning.

7. Evaluate the Success of Your Virtual Retreat

As soon as our virtual retreat ended, we sent a feedback survey to our entire team.

We wanted to know exactly what they thought of our event—and we wanted to know while the experience was fresh in their minds. What did they enjoy about it? Where could we improve? And do they have any ideas for a virtual team retreat in the future?

A week later, my co-founders and I got together to read through the feedback we received. We then met with each department head to see if they had additional information to share with us, based on the conversations they'd had with their teams.

While it will take you time to gather and process feedback, it is 100 percent worth the effort. You can use all that info to plan better events in the future. And employee satisfaction will rise when they know that their opinions are taken seriously. Don't skip this!

Build an Engaging Virtual Retreat for Your Team

If you want to plan the best virtual retreat, you need to make every moment engaging.

This is difficult to do—but not impossible. As long as you follow the tips, tricks, and best practices in this article, you'll be fine. How do I know? Because it worked for us!

Our virtual retreat was a smashing success. Not because we're better at events than other people. But because we focused on the right things. We knew what we wanted to accomplish, we kept things simple, and we prioritized our employees' experience.

Just remember, team building isn't something you do once a year, or even once a quarter. It should be a continual process. This is especially true for remote teams, as your employees don't see each other on a regular basis, which makes it tricky to build company culture.

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. Keep pushing to improve, and your team will keep pushing to give you their best in return. Your virtual retreats are no exception.