How We Pulled Off an Epic Virtual Retreat in 2020

In non-pandemic years, the Hubstaff crew shuts down karaoke bars, brainstorms exciting new initiatives, and clinks glasses in 12 different languages during our annual retreat.

Our 100% remote team works worldwide, so the retreat is our best shot at getting together, working across teams, and learning about the real people behind the Zoom windows.

Even though 2020 was a tough year (to say the least), we still had a lot to celebrate.

However, the health risks made gathering in one place impossible and unwise.

The question was: Can you replicate the bonding, teamwork, and camaraderie of a company retreat if it’s all done virtually?

Let’s find out.

Hubstaff’s 2020 virtual retreat

Why host a virtual retreat?

It’s true; we could have skipped a year and waited until the team could safely gather in person.

Moving an in-person retreat to a virtual format would be a massive undertaking. Hubstaff grew from 55 to 79 people in 2020, which made planning a virtual retreat feel like playing time zone Tetris.

We had new team members to train, product improvements to launch, and lots of new Hubstaff users who needed our help figuring out this whole remote work thing.

We were in the middle of a pandemic. Everyone was dealing with higher stress levels.

And that’s precisely why we knew we couldn’t skip our retreat.

Annual retreats are our chance to step away from the daily grind and look at the business from a different perspective.

Retreats are a time to zoom in and zoom out. Plus, they are fun.

Even though we couldn’t travel and see each other in person, it was still crucial to find a way to accomplish those things.

As a bonus, if we could figure out a virtual version of our retreat, more team members could participate in the future. When in-person retreats resume, anyone who couldn’t travel for it can join from home.

Our challenge was to figure out how to:

1. Bring the team together,
2. Unplug and give ourselves the space to think about our work
3. Build genuine relationships

— all without being able to see each other face-to-face. And that was just the beginning.

The challenges of planning a virtual retreat

In our nine years of business, 2020 was our first time trying an entirely virtual event.

We knew how to work remotely, but we were less prepared to have fun remotely. Being new to virtual retreats presented some challenges.

Time zone battles

Hubstaff is global. Imagine trying to coordinate events for more than 60 people who live in a dozen different time zones.

If some Hubstaffers kicked off their first retreat day at 9 am, it would be midnight for others. The challenge was finding the common times for activities across teams and departments.

Sometimes, it’s hard to find overlapping hours

Balanced schedules

Our hackathon teams needed time to work together to finish projects and time alone to focus. We also wanted to gather the whole company for the keynote address and hackathon presentations.

As much as possible, we tried to coordinate meal times so we could eat together and replicate retreat downtime.

The key here was to make sure each time zone had a balance of deep work, fun, and relaxed interactions.

Building excitement

Group events are only fun when there’s a group of people who participate. For this virtual retreat to be a success, we needed to host fun events that people wanted to join.

Truthfully, no one expected the remote retreat to be like the real thing. Being at our desks instead of taking in Portugal or Mexico’s sights might have contributed to the challenge.

Knowing that, how could we do our best to get the team excited and looking forward to the retreat?

Business as usual

And then there’s the regular workweek.

We knew that it would be harder to let emails sit unread during the virtual retreat and leave tasks un-checked on our to-do lists. Our schedule had to allow time to get work done but still be engaging enough to keep people from zoning out.

The team rose to the challenge. Here’s how we did it.

How we planned our virtual retreat

One of the best things about the Hubstaff team is that everyone is willing to step up and take on a challenge. We were once again astounded by our colleagues.

First, we started with the “boulders,” or the key events of the retreat.

For example, our hackathon is essential, and we wanted to expand it. We needed an all-star keynote to set the retreat theme. And, we knew eating and drinking together is a retreat must-have.

Those few things gave us a starting point. From there, we got creative.

1. We surveyed the team and picked the most popular activities.

Surveys and signups on Slack made this easy.

First, we suggested some ideas that we thought people might like to get an idea of attendance. Seeing who responded helped us decide how many sessions we needed to plan and which time zones to cover.

Next, we invited people to suggest events they’d like to attend or host.

Most ideas made it to the calendar. As long as we could find someone to lead and people who wanted to attend, it was worth scheduling.

2. We made sure the technology was solid.

Since this event was completely virtual, we needed the right tools.

Everyone who hosted something got a premium Zoom account to control and record their events.

For gaming sessions, we used Discord. Our CEO, Jared Brown, created dedicated lobbies for gaming groups in different time zones. We still use the same Discord lobbies on our weekly game nights.

In the days leading up to our retreat, we set aside some time to test equipment and make sure everything worked as planned. There were a few hiccups, but overall it was pretty smooth.

3. We built a schedule with some wiggle room.

For optimal excitement, we packed the schedule so that there weren’t long stretches with no activities.

A lot of work went into this schedule so there was something for everyone

Job van de Voort, co-founder and CEO of Remote, gave our keynote address. Nobody wanted to miss that.

From there, Hubstaffers were free to choose their virtual team building activities. Or, they could decide to take a break from the retreat.

There was plenty of flexibility to get work done, rest from video calls, and focus on personal priorities.

We also left plenty of room to suggest activities on the fly. If you didn’t like any of the options on the schedule, you were welcome to strike up an impromptu game of Among Us or get some people together in the Zoom lobby.

4. We got into the details of each event.

Team members who were hosting a session were responsible for most of their prep.

Some things were easy to organize. For the street streaming sessions, we just needed some time on the calendar and a Zoom link. As long as Sergey was available to stream from his tour of Montenegro phone, we were ready to go.

Other sessions needed a lot more planning.

For example, we planned our cooking classes days in advance.

The chefs made a list of ingredients and equipment, then followed up with registered attendees to see if they needed any ingredient substitutions for their region.

Digging into the details helped us decide where to put things on the calendar. If an event required a lot of prep time, we didn’t ask the same person to host something else right before.

5. We trusted the team.

Hubstaff hires great people who are motivated and proactive. We bring it.

During the retreat, our focus wasn’t on managing people and events. It was about providing the framework and resources, then letting people take advantage of it in their own ways.

Everyone’s experience was a little different. That’s something we can’t get at a physical retreat.

How it went

In a word: SUCCESS! *cheers emoji*

We kicked off bright and early (at least in some time zones) on Day One.

As we expected, Hubstaffers took the initiative to host more gaming sessions, more get-togethers, and more coworking sessions than we put on the calendar.

Slack was our central hub for communication. To keep it from getting too messy, we set up a #retreat-2020 channel. It was a central place to collaborate during planning, and we used it to stay in touch on retreat days.

Here are a few of the best ideas from our three retreat days.

The meta-thon

Hackathons are usually developer-focused. Ours wasn’t. That’s why we called it a meta-thon.

The marketing team chose to work on two different projects.

The goal of this event was to get everyone thinking at a higher level. Every team chose an important project that they wanted to work on to make Hubstaff better.

We needed to look at things from a fresh perspective. We asked team members to work on a project they cared about and wanted to see become a reality.

This part of the retreat offered time to review, reflect, and improve.

One team built a darkmode mockup for our app. Another worked on a whitepaper to support our growing sales team. Support built a detailed playbook to onboard new Hubstaff users.

One of our main goals for this retreat was to get away from daily distractions and think strategically.

Team, I think we did it.

Hubstaff University

Hubstaff team members bring a deep level of expertise and talent to the table. Our Hubstaff University events were a chance to share those skills.

Cody and Adrian taught us about photography

Hubstaff University was a collection of 30-minute classes taught by team members. The hosts and participants talked about topics they enjoy. These were off-the-cuff, real-world sessions, not boring lectures.

In some classes, talented Hubstaffers talked about the exciting things they do in their jobs. Peter taught us about A/B testing, and Bobana hosted a course on SEO.

Other classes were not work-related at all. Michal led a session on investing, which led us to start a new Slack channel after the retreat.

These sessions were valuable for more than just the obvious reasons. We got to know the hidden talents and passions that make our teammates unique. And we noticed how many interests we share.

Another retreat mission accomplished.

Gaming sessions

We have a lot of gamers at Hubstaff.

Gaming during the virtual retreat ranged from short Skribbl sessions to hours of League of Legends. There was a game for every type of gamer.

By the end of the week, gaming was a virtual retreat highlight.

Online gaming is fun, and it’s easy to do when you can’t be in the same room with your teammates. We could indulge in some friendly competition — and a lot of laughs — without worrying too much about locations and time zones.

Gaming was so popular that we still do it months later. Every Thursday, Hubstaffers get together with friends in similar time zones to play the game of the week.

We also now have a #pub-trivia slack channel where we have a short quiz game every Friday. For some of us, pub trivia is a fun way to start a Friday morning. Others join in on their lunch break. Some of our European teammates hang out after work like a virtual happy hour.

We still connect across time zones and cultures to have fun together, and it’s all because of a trivia game held over Zoom during the virtual retreat.

Cooking classes

Here’s another activity that we’ve continued post-retreat: cooking together.

Our retreat cooking classes inspired the #cooking channel in our company Slack. We love sharing pictures and recipes of our favorite regional cuisine.

For the retreat, we wanted to showcase our culinary skills and share some delicious local recipes. Eyal volunteered to make chicken and mushroom risotto, and Kitty taught us to make her gran’s chicken and dumplin’s.

This risotto recipe is delicious.

Finding the right timing for these classes was tricky. Some people had risotto for breakfast, and others ate it for a late dinner.

We learned to record and share these live cooking classes so that others could replay them and cook along at their mealtimes.

The murder mystery

Team-building games can be fun, and we wanted to try something new for our virtual retreat.

For obvious reasons, the escape room we’d done in years past wasn’t on the table.

We worked with a company called Outback Team Building to solve a murder mystery puzzle over Zoom.

To accommodate everyone, we scheduled two different sessions. People who played the first mystery game had to be extra careful not to talk about it until the second group had their chance.

The murder mystery was fun and insightful. We learned a lot about paying attention to details and listening to each other when solving complex problems.

Who doesn’t want teammates who can do that?

Lessons learned from our 2020 virtual retreat

Upon reflection, this retreat was even more successful than we expected. Sadly, we didn’t have time for desk karaoke.

Our “Hubstaff University” classes were fantastic. I particularly enjoyed learning more about the stock market from our Tasks Team Lead Developer, Michal.

-A happy Hubstaffer

We had such a great time that we plan to do it again.

Even after the pandemic recedes and it’s safe to travel again, we’d like to have a virtual retreat and a physical retreat every year. The connections we made and bonds we created were easier to continue because we were already working from our homes.

Our 2019 retreat

Would we do anything differently?

Absolutely. There’s always room for improvement.

It’s clear that we love getting together, whether it’s online or in person.

Next time, we’ll:

• Try new activities and ask others to host events
• Give ourselves longer stretches for regular work instead of a quick half hour here and there
• Consider scheduling activities over a week instead of just three days.

The most important thing we learned is that we can — and should — accomplish all of our goals with significant virtual events like this. We’re glad we went for it.

Tips for hosting your own virtual retreat

Hearing about our epic virtual retreat was, makes you want to host one for your team, right?

This was a live stream from our virtual retreat — but maybe it’s a future retreat destination, too

If you put together an event like this, here’s what we recommend.

• Go all in. Planning an event like this is a lot of work, whether it’s in-person or online. We worked hard to make this work for our entire global team, and it was worth it. Your effort will pay off.
• Give people time to step away. Zoom fatigue is real. Even when you’re having fun, sitting on video calls for hours is exhausting. Give your team a choice of events so they can find something that suits their interests. More importantly, make sure that you give them the option to take a break. The retreat is supposed to be fun.
• Expect some work to pile up. You shouldn’t neglect your customers, but you can afford to take a break from your to-do list for a couple of days. Give yourself and your team some time to work on the big picture. Remember – everyone’s insight is valuable. Create space for people to speak up.
• You don’t have to wait until your retreat to do things together. Host a cooking class. Play a murder mystery game. Get together on Fridays for some trivia in Slack. You don’t have to host a multi-day event to connect with your virtual team.

Want more tips and expert advice on how to keep your remote team connected? Check out these articles:

The Ultimate Guide to Remote Communication

How to Build a Great Remote Culture

Exclusive Report: How the Pandemic is Impacting Remote Work

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