How To Create a Virtual Retreat Your Remote Team Will Love

February 18, 2022

With the pandemic, you might have switched to a remote or hybrid team, and may be brainstorming how you can still plan your annual retreat with team members now working from home.

Last year, we hosted our largest annual virtual retreat yet, highlighting how technology works best when it brings people together. With over 100 employees spread across 25 countries – our annual retreat proved that virtual relationships can be just as meaningful and enriching as those developed in person.

Here's a guide based on our experience, how we improved our company culture and engagement with a fun get together that all our employees loved.

Why do a virtual retreat?

We’ve all attended enough virtual events on zoom to know they aren’t always the most exciting. But these experiences are what motivated us to try and build something different.

We needed a company retreat that would successfully capture the same feeling of togetherness and engagement amongst our team as a physical annual retreat.

So the main objective of our virtual retreat was to facilitate meeting new people and experiencing the event together in a fun and unique way. One of our success metrics was the number of new people each person met and if they Slack messaged that person individually after the retreat to talk about non-work topics.

As it was an annual event, we committed to creating 3-hour sessions per day for 5 days.

We challenged ourselves to design each team-building activity, session, and day in a way that would ensure that every attendee left the event feeling a certain way about their own unique experience.

How to host your virtual retreat?

1. Planning challenges

Having a remote team with people spread across 25 countries meant our biggest challenge was navigating different time zones. We overcame this obstacle by choosing a 3-hour time slot when 90% of our team would be awake. It's also possible to plan asynchronous activities that your team can do at home.

We also needed to be planning activities that were accessible to all. For example, we initially wanted to do a gingerbread house activity or a DIY cocktail making class. But it was near impossible to find vendors who could deliver materials and physical items to all of our team members.

But we decided not to pursue these ideas as we wanted to make sure nobody felt left out. So our rule was – if even one person couldn't do it or get access to the items needed for the activity, we wouldn't do it.

Finally, the last unexpected speed bump that we hit was making sure that our swag kits reached the entire team timely. While in many cases, the kits were delivered seamlessly in less than a week, for many of the countries, we had to navigate complicated custom requirements that we did not anticipate. So make sure you plan ahead your first virtual retreat and make sure anything that needs to be delivered is taken care of first.

Luckily Style Gifts Ltd. came to our rescue and handled our Swag Kit supply and distribution. In addition, Style Gifts were an invaluable support partner who were by our side every step of the way to assist with any hiccups – logistical or otherwise.

We're also now partners with Hoppier and other amazing food and beverages vendors who can help deliver food to your virtual team building activity, lunch and learn or happy hour.

2. Building hype, how we got the team excited

Unlike in-person retreats, virtual meetings can leave attendees surrounded by distractions that are just a click away, and there are many opportunities to zone out. We knew we would have to ensure our content was highly engaging and was delivered to people when they were not under pressure with work commitments.

Slack announcements proved to be a great way to excite people about various parts of our event programs – from salsa dancing, drag performances, and rap battles to prizes and raffles. We posted around three announcements a week with GIFs and used our email list to send countdown emails to our entire team.

We also hired a video editor to create hype videos to tease our planned team building activities creating mystery and excitement. We found someone on Fiverr to help us with that, and it turned out to be very effective in getting people excited.

We also asked volunteers to put their names forward to join in a few parts of the program as hosts/announcers for the awards and talent show. Many actively engaged with us during the planning stages and participated by owning their own part of the schedule.

We knew that everyone wanted it to be lighthearted and fun from our first committee meeting. Barry encapsulated that in the GIFS he created of our leadership team to get people laughing ahead of time.

3. Logistical preparation

To ensure we captured every employee's voice, we started with a ten-person committee. But as we progressed, we condensed our efforts to a core team of 5 who planned this mega video conferencing event in 6 weeks.

Preparing for the global distribution of swag kits began by deciding the number of items to give away, what prizes to give, the total budget per person, and finally, finding the best supplier for the location. We also had to ensure that the supplier could ship the items individually across different countries.  

Logistically, this involved weekly meetings to work on one spreadsheet with all the details such as budget, prizes, attendance, run of the show, etc. Closer to the event, we have more frequent meetings as floor plans changed and everything needed to be coordinated with the day's theme. The best one I would say was the Oscar's-like red carpet event!

For the physical plaques won by our Annual Awardees, we sent the winners a physical glass plaque that we sourced from each country's local suppliers. The biggest lesson we learned was that we should have confirmed logistics a minimum of two months before the retreat week. Although everything went to plan, we were cutting it fine with deadlines and would give ourselves a little longer to prepare next time.

What to do in your annual virtual retreat?

Here are some of the virtual team retreat activities we did and our takeaways.

Day 1 – Retreat Kick off!

Dress-up theme: crazy shirt/hat

Salsa Dancing

We worked with the amazing agency GetSomeClass, run by Joseph Gerstel, to bring world champion Latin Dancer Charlene Rose to teach the team how to Salsa!

We wanted the first activity we did to be more interactive so structured this activity as a fun competition where groups of people would come up together to have a short "dance-off." The team at Remo is incredibly competitive so dancing along with Charlene turned out be the perfect icebreaker for day 1.

The Secret Library

Are you curious to know what happens when you cross improv comedy, interactive theatre, and a bookworm’s dream? We were too. That’s why for the second half of the event, we booked an hour-long session with Secret Library’s Origins Puzzle Theatre.

We got to jump between tables and work collaboratively to solve clues and find the missing pieces to unlock the final door (not to mention interrogate all 9 of their brilliant live actors, like a real game of Clue).

Day 2 – Department presentations and a Mentalist performance!

Dress-up theme: superheroes

Department Presentations

It was crucial for everyone in the company to understand what each department did and celebrate achievements from all company areas. We grew from an 8 person team to a 100+ person team in a very short period of time, so being able to shed some light on how all departments worked together would be an excellent way for people to understand how they could potentially collaborate on future initiatives.


We ran two trivia games using AHA Slides that were designed to help people get to know each other better.

The advantage of remote work is being able to set up elaborate (and not so elaborate) home offices, so our first trivia game was themed "Who's workstation is this?". We then had people guess whose work environment was shown in the pictures.

The second trivia theme was "Two truths and one lie", which was inspired by the regular new joiner announcements that we do in our Slack channel, where we write two truths and one lie about each new employee. So this trivia game tested how well the team knew each other.

Mentalist Show

We had the amazing mentalist, Larry Soffer, perform for us in the second half of day 2. We loved Larry's show because not only did he have amazing tricks and illusions, but his performance was also completely interactive as he brought people up on stage to do the sets together. This delighted our audience, and they really enjoyed the pure hour of entertainment that Larry brought us.

Day 3 – Mental health and Drag performance!

No dress-up theme - everyone takes a break!

Mental Health

Mental health, wellness, and mindfulness are often discussed at Remo – we are acutely aware of the dangers of overworking and burnout associated with remote work. Without being in a physical office, it's also challenging to understand how people are feeling on a day-to-day basis just through Slack channels, video calls or email communication.  WE wanted to give people time to think about and improve their mental health.

Olivia Bowser from Liberate was our facilitator, and she shared practical tips and small additions to our daily lives that would help with mindfulness and self-awareness. The main goal was to reflect for an hour, train our mental fitness, and decrease our stress levels.

Drag Performance

We know this is not a convenient option for most annual retreats. But we knew we had to do something unique, fun, and silly to get people out of the regular small talk and superficial work conversations. This gave them the opportunity to truly get to know one another better and to show a different side of themselves – something different from their "work personality."

So what better way than to use drag– an art form that embraces and empowers difference and self-expression? We had two fabulous drag queens facilitate an hour of fun, with a drag makeup challenge, an unconventional scavenger hunt, and a lipsync challenge.

We immediately felt a positive change in everyone's attitude towards one another after the drag performance, as even our senior level management went all out to participate and have a little fun.

Day 4 – Know your colleagues and talent show!

Dress-up theme: national costume

Freestyle Rap Artist

Joseph also arranged a fantastic rap/comedy performance by Chris Turner. Chris' rapid freestyle raps and improvisation skills amazed our entire team. We particularly enjoyed his rap segments from audience prompts (he even challenged us to give him obscure words, where we ended up giving him topics like "Plankton" and "Indian Weddings"). Even with our team scattered across the world, Chris' performance united us all, brought huge laughs, and was unanimous.

Structured Networking

We organized a few different structured networking sessions and they turned out to be the perfect fun activity to run on Remo. Since Remo was built for small group conversations where people can interact in real-time and create meaningful connections. This was also ideal for people to meet up and speak with people on the team that they didn't know.

To avoid too many awkward silences, we attempted to make these portions extremely structured and incorporated as many conversation starters and prompts as possible. We found this made it much easier for people to get to know one another without struggling to discuss common topics. Here are a few of the ways we structured it all:

1. Never Have I Ever:

Most people are extremely familiar with this game, making it an easy one to incorporate. We made it even more seamless by including 50+ never have I ever statements on the whiteboards on each table within Remo, so people could use those instead of making any up on the spot if they didn't feel comfortable. Each person had 3 lives, and once they ran out of lives (by admitting to the various never have I ever statements), they would move tables to join a new group of people.

2. Table Prompts:

We utilized 3 main features of Remo for this one. 1) Editable table names, 2) Shuffle mode, 3) Timer. We first changed tables name to conversation prompts such as “Share your proudest moment this year,” “Share an embarrassing story,” “Discuss your favorite movie or TV show and why?”. Then, we would set the timer for 5 minutes, and people would use that time to connect and discuss based on the table prompt. At the 5 minute mark, we would then hit “shuffle,” which would immediately shuffle up our attendees, and people would repeat again but with a new table prompt and a new group of people. This was one of our most popular segments throughout the whole retreat, and people really enjoyed the structured flow.

3. Vision Boarding:

Given that we were approaching the end of 2021 and were having a lot of internal team discussions about the company vision of 2022, we wanted to give people an opportunity to discuss and talk about their own personal or professional aspirations for the year ahead. We broke up into small teams to chat in more intimate groups.

4. Meme Challenge:

We broke everyone up into small groups of 5-6 people, and using an easy meme generator, we created a fun hour or creating memes about work, funny things that happened at the retreat, and different people within our teams. This turned out to be a massive hit as people got extremely creative, and we all got a kick out of different Remo-specific memes, which showcased how funny our entire team is!

5. Talent show

The talent show was one of the most popular events from our retreat last year, and we wanted to do it again. We got 2x more talent submitted and what we found is that this is one of the best ways to learn about each other and be amazed at each other’s talents.

Day 5 – Awards show!

Dress-up theme: Oscars/black tie

Talent and Awards Show

To focus on one of our core retreat goals, which was to celebrate our team's achievements, skills, and talents, we had both a talent show and an awards show. Our talent show was again a massive hit with the team, with over 12 different acts ranging from musical performances to cultural dances to cooking shows and party tricks! In addition, we planned out our Oscars-inspired award shows to encompass both serious and funny aspects, ranging from our "Unmatched Dedication" award through to our "Fashionista Award" and "Loudest Typist" to keep the awards show lighthearted and fun.

Scattered throughout the week, we included prizes for best dressed (we had a different dress-up theme each day!), raffle prizes (Christmas hampers, AirPods, Nintendo switches, and more!). Everyone also got a food and drink allowance to ensure people felt they could have a good time with beers, champagne, pizza, sweets, or whatever they fancied.

Overall feedback

An event feedback form was sent immediately after the event, and it was delightful to receive a positive rating of 92.2%. In addition, all of the retreat goals were met with favorable responses, especially our goal of "Celebrating and Recognizing our Amazing Talent." We set out to unite 100 employees in more than 25 countries and provide a feeling of togetherness across all our teams. Although technology made it all possible, it was a simple rule at the heart of our virtual retreat that was the secret to the event's success.

“So our rule was, if even one person couldn't do it or get access to the items needed for the activity, we wouldn't do it.”

By designing each activity, session, and entire day around ensuring every attendee would have a unique experience, we succeeded in recognizing the talents of every employee with no exceptions. However, we also learned a few lessons along the way which we will improve on for future team gatherings and improve on the 92.2% so that every employee feels they can contribute and help shape our culture at Remo.

Helping both introverts and extroverts shine without anyone feeling overshadowed is notoriously difficult in any setting. But by recognizing the strength in each other and celebrating the diversity of thought, we believe that the virtual retreat enabled us to collaborate closely, connect as one team while having a whole heap of fun too.

Our retreat also influenced our employee's perspective of the company. Many of them have come to appreciate our culture, thoughtfulness, creativity, and most especially, our drive to humanize the virtual experience. Speaking of humanizing the virtual experience, our employees saw the true power of our awesome product, and they have even given some suggestions to make our product even better!

If you scratch beneath the surface of the light-hearted fun in everything from salsa dancing to freestyle rap contests, it was clear for all to see how our people were connecting in a more authentic way. It also highlighted the importance of the human connection when building relationships in a virtual environment.

As for their favorite days of the retreat, the overwhelming choice was the fourth day which featured the talent show and freestyle rap. A close second was the second day with the mentalist and let's not forget the third day with our very own drag queen performances. We will be asking everyone for more ideas for our next retreat and we are already confident that next year will be even better.

It's no secret that employees who feel unappreciated are beginning to quit their jobs and fuel the great resignation. By contrast, here at Remo, every employee is appreciated. Every team member is also passionate about breathing new life into what we do together, and it shined throughout during the retreat. Although our virtual retreat proved a big hit with everyone, we are excited to see what everyone can play a part in making our next one even better.

Over 100 employees in more than 25 countries across multiple time zones joined forces to show the difference we can make as a team while celebrating the unique talents of every employee. By celebrating our wins and the difference we can make together, it felt like we won't just succeed in humanizing online events around the globe, but we will collectively take them to the next level.

If it's your first time on Remo, and want to know how to leverage it's capabilities like we did in our virtual team retreat, just get a free plan, join a guided tour, or check our pricing.

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