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How We Planned a Virtual Retreat During the Covid-19 Crisis

· Posted by Natalie in Company and tagged · 5 Comments

Blog posts along the lines of: “10 things you must do to have a great company retreat,” always make me cringe. I don’t like speaking in absolutes.

Your perfect retreat is going to look different than our perfect retreat: you have different team members, different needs as a company, and a different company culture than we do.

This year however, I was convinced of one thing: there is no perfect company retreat. What I mean by that is, there is no one perfect retreat, even for us.

Last year we had a great company retreat. It was a major shift from our retreats of recent years, and was what our company needed. Our plan for 2020 was to maintain most of that format and location, iterate slightly, and change the topics to match this year's company-wide projects.

But as perfect as that retreat was for 2019, not only was it logistically out of the question, its content type and style would have been completely wrong for 2020.

The “perfect retreat” then, is one that learns from past experiences, while recognizing the unique needs of your team and company in the current moment.

2020 challenges and solutions

This year obviously brought some unique challenges. Here are 3 main problems we analyzed while designing our first virtual retreat, and some of our solutions to meet those needs.

Logistical Challenge: We are spread across 2 continents and didn’t know what stay-at-home phase everyone would be in.

Solution: Keep it as simple as possible: gifts or home food delivery might be fun, but we didn’t entertain these ideas this year.

Since the original plan was a retreat in Bologna, the retreat logistics team had started purchasing retreat gifts. We’ll get these to everyone eventually, but the stress of trying to send them in time wasn’t worth it. We didn’t want some people to have gifts and others not, nor were we comfortable adding risk for workers in the shipping supply chain during the most restricted time in the pandemic shutdown.

The logistics team did organize a nice virtual gift for the 3 of us celebrating our 10 year anniversaries. Although the print copies weren’t yet ready, Mike, Paolo, and I were surprised and delighted by slideshows of the photo memory books Joy created for us.

Balsamiq Photo Memory Book

Solution: Keep supply lists optional and flexible.

While we had some activities that included suggested supply lists (cocktail-making and a beauty care session to name two) we made sure none of the items was essential for participation. We offered alternatives approaches and tried to make sure all felt welcome.

These ended up being great creative restrictions. For one of our 3 week-long Creative Challenges, Amanda chose a "Paint Frida Kahlo" tutorial from Paint with Lovejoy which was very adaptable for different media. Though some of us had acrylic paints (which the video is designed for), we had submissions using 3 pencil types (regular, colored, and watercolor), crayons, watercolor paints, sharpies, and perhaps most creative, highlighters Peldi pillaged from his son’s school supplies.

Frida Kahlo Paintings with Lovejoy

Solution: Explore new uses of digital tools.

We’ve been a remote-based company for over 10 years now, so using online digital tools to communicate is what we do every day. However, we explored options for using our tools differently. We use Zoom for company-wide meetings but had never used its breakout room feature.

Incorporated into a skill-sharing session “How To Effectively Communicate a Project,” leaders Laura and Amanda started the entire company together in one room for a session intro, then quickly broke us into 5 pre-assigned groups with discussion moderators.

skill-sharing session

It worked great, and we’ve already used it again in a Kaizen Monthly meeting (where we present and discuss company-wide issues, policy changes, and initiatives). We like company-wide discussions, but having 33 people on a call doesn’t usually result in fruitful and inclusive discussions.

This feature makes it easy to start together, break apart, and come back for a wrap up. It allowed for more productive conversations, and a chance to talk with people we don’t normally work with.

Emotional Challenge: It was difficult to know how and what to plan when many of us were struggling with major anxiety and stress.

This was definitely our biggest challenge. Our planning team had been full of enthusiasm for the original retreat, but when we realized in early March we needed to cancel the in-person event, deciding what should replace it was difficult. We asked the company to keep holding the week for a virtual retreat, but purposefully delayed any deep brainstorming about what we should do.

Solution: Wait to discuss ideas until 1 month before the event, as predicting how we’d all feel in 2 months was impossible.

This was a very atypical choice, and particularly not typical for me! Our decision to keep logistics extremely simple made it possible, and it ended up being the right approach.

On the Meyers-Briggs personality test, I’m a pretty strong J — meaning I love plans, but in this case making plans gave me anxiety. I couldn’t be sure I would have the emotional energy to do what I promised. Probably like most of you, we each found our mood fluctuating wildly in the past months — sometimes hour by hour!

So we leaned into the company, and simply asked them. One month before the retreat we presented a very basic approach, and asked for input. We heard what everyone was interested in doing, and even more importantly: what they would be excited to lead.

Retreat activities ideas

Any idea put forward — no matter how wacky — that had a willing leader, was in. Interesting ideas that didn't have an immediate raised hand behind them, were out.

In 2019 we had purposefully worked to give everyone leadership roles during the retreat. The shared ownership last year really showed this year. Even in the midst of the stress of the pandemic, those who were able, rolled up their sleeves to make the week happen.

This short timeline did work, and in some sense made planning fun. We brainstormed quickly, didn’t overthink ideas, and had very low expectations (we tried to reject anything that caused stress). It ended up being a little too tight of a schedule, particularly because I needed to take 4 days off related to pandemic stress and anxiety, but even with this, we recovered.

Solution: Keep almost everything “opt in.” Communicate that everyone should do what they personally needed to recharge — even if that means not participating.

This was a major change from last year. For about half of each day last year, participation in activities was pretty much expected. This year, we only had a total of 3 hours in the entire week that people were more or less expected to participate, and another 3 hours we hoped people could all attend. The retreat was named “Choose Your Own Adventure.”

We knew that people were experiencing a whole range of emotions: Social and fun might be what they needed. Doing focused work might be the distraction they wanted. Or they might prefer to take very light workweek to be with their families. We tried to communicate that all or any of that was ok.

Kickoff Retreat video by Virgin
Virgin helped set the tone with a pre-recorded kickoff video from his pool — complete with relaxing spa music, and special pool assistance from his daughter.

Solution: Keep content light! Focus on relaxation and fun.

We wanted to have some work content and skill-sharing, but hard conversations like company strategy or our salary system — things the retreat seemed great for last year — didn’t seem right for 2020. One of the 3 “work” activities we chose was a work shadowing. It was very simple: pair up people who don’t usually work together and have them talk about what they do.

Tommaso designed the activity page entitled “The M(eow)arvelous Experience of Work Shadowing” which made even the idea of watching someone else work sound fun. I still chuckle thinking of the page.

Rule of Two - Work Shadowing Session

This was an extremely popular activity. Everyone did at least 2 hours: one as a Cat and one as a Worker, and others added on additional hours during the week.

Outside of the 3 “work” activities, the rest was focused on fun. We had 3 other “3's”: 3 Creative Challenges, 3 social gatherings, and 3 rest and relaxation sessions.

Collage of photos from the 2020 Virtual Retreat

Some of these activities were downright ridiculous. As Peldi told me afterwards, he thought before many activities “This is either going to be lamest or the most awesome thing ever.” They each were awesome because the entire company “brought it.” The program team had set the right tone, but over our 11 year company history we have built a high level of fun, trust, and sense of friendship that I think really shined during this difficult time.

I’m not certain some of these “events” like the “Disco Dance Party - All I Wanna Do Is a-Zoom-Zoom-Zoom and a-Boom-Boom!” or “Beauty Care with Laura and Lei” would work well with a team who had never met in person before. They relied heavily on our willingness to be all-in silly together. But some activities like a US Happy Hour with Family Feud organized by Val and Alasdair, or the cocktail-making demonstrations done by Laura, Andrea, Paolo, and Peldi would be more adaptable to a newer team as silly, but more approachable ice breakers.

Timezone Challenge: How do we feel together and have fun, with only 5 hours in common?

Solution: Have asynchronous activities.

One great win of the week I think was the idea of asynchronous activities. We had 4 activities that could be completed at any hour of the day. One was a Security Challenge and the 3 Creative Challenges.

Although for the most part we did the activities on our own, they produced a surprising amount of togetherness. The writing challenge “Storytelling with Natalie” was simply writing a personal story (funny, serious, or otherwise) in a Confluence Blog Post. We already have a Slack channel with notifications when a personal blog post is published, so throughout the week we were notified of the 9 stories people had written, and could spend time commenting back and forth on the personal tales that ranged from very serious to incredibly funny.

We also brought all this asynchronous creativity together in a “Creative Challenge Celebration” video call on the last day of the retreat. I gave out “awards” for writing, Amanda showed a slideshow of all the paintings created, and the most uproariously funny time of the week was Luca’s presentation of the Lip Sync Challenge videos our teammates had created during the week.

I had to lie down for a short nap after watching those videos because my head hurt from laughing so much.

Paolo Lip Sync Video challenge
Paolo, in a masterpiece of video editing spicing together the original video with his own, Rick-rolled us.

Solution: Find ways to use the entire time zone range.

At a normal retreat we have hours and hours together. This year we were very limited with overlapping work hours (only 5). Asking our European colleagues to spend all their evenings doing work stuff — even fun stuff — was a tough ask, particularly because unlike our regular retreats, we were all at home and have family and other life obligations to balance.

In order to meet this challenge, we did a few things in addition to asynchronous activities:

  • Targeted use of the Golden Hour: We have one hour a day (8am Pacific, 10am Central, and 5pm CET) where we all are online each day. We tried to maximize this hour by putting nearly all the “required” or “recommended” activities in this time slot.
  • Double sessions: Our monthly Media Club met this week, so we arranged to have a lunchtime movie watch party in Europe, and separate dinner time US watch party in advance of the discussion session.
  • Recorded Sessions: We recorded the sessions that took place outside the Golden Hour so that Balsamici could replay them later. (We had a few exceptions for good reasons, including the Beauty Hour where most of us were doing facials or had put honey and olive oil in our hair. 😊) I know I enjoyed being able to listen to a session I didn’t attend, and Val even rewatched the US Happy Hour. She had been there, but wanted to enjoy the laughter again.

To balance the schedule, we set a few US things in the evening, since folks in Europe had a number of evening sessions. We made sure to schedule some events during the EU day that the US would need to watch by recording. All of this grid of timezones was pretty clearly communicated in a Google Sheets-based calendar Amanda set up during brainstorming and I adapted as I pieced the week together.

Wrap up: Ideas for the future

We still would like to meet in person next May if we can, even if it is in small localized groups. In-person time is extremely valuable for maintaining healthy remote-based work relationships.

Although a lot is unknown, what is clear to me is whatever happens in 2021 will be different no matter what: we’ll see where we are at and what we need then.

But the virtual retreat experiment was a success, and we’ve decided to try out a few things to build company connection, spacing some activities out all year long:

  • Three work shadowing sessions
  • Three skill-sharing workshops
  • A 3-day mini virtual retreat in the fall, focused on social and fun things

(Apparently we really like 3's!)

We also decided to improve our monthly All Hands Meeting to contain more valuable content, such as lightning talks.

Have you planned a virtual gathering for your company during the pandemic crisis? Has your company tried new ways for building teaminess? We’d love to hear your ideas for staying connected in 2020!

Natalie for the Balsamiq Team

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Comments (5)

  1. Hi Natalie,

    Thank you so much for sharing this! We’ve been thinking of various ways to conduct our virtual retreat…our small team is spread across 5 time-zones.

    I wanted to know 3 things (continuing your tradition :-p )

    1) How much time and effort did it take to organise this retreat? do you have any shareable content on plans and templates?

    2) In hindsight, is there anything that you’d definitely not do or could have done differently?

    3) Can you please share some more details on how did your organise the assigned groups session? How was it assigned, what was discussed in each group? was it the same content? how did to assemble and then share with the rest of the team.

    Thank you so very much for this transparency and insight into your processes.


    • I think it is me that keeps making threes! Yesterday I outlined a new roadmap for something and it too had 3 areas. 🙂 I am glad I am not alone.

      1. This retreat went together very quickly — but we worked hard to share the load across the company. At the 2019 retreat everyone had at least one responsibility. I believe we were building off that involvement and leadership this year. It made it easier to find volunteers willing to plan something. I’ll happily send a few examples of our information pages by email. I’m not sure if they will be useful but we’ll see!

      2. I don’t know that we would do much differently for that May retreat — we were all in a strange place emotionally, so the choices I think were right for that time. But one small change for the upcoming Social Mini Retreat is we are emphasizing more that no project or team meetings should be scheduled during the retreat days. This upcoming retreat is social only, and most activities will still be optional, so some people may chose to do individual work (and some jobs like support, can’t really be put on hold). However, during the May virtual retreat, some project teams scheduled meetings during the week even though we suggested they not. Having meetings scheduled made some people feel pressed to do more regular work than was absolutely necessary, and felt they couldn’t relax and focus on the retreat.

      3. We use both assigned and random groups depending on the session and the desired outcomes. The random assigning by Zoom is very easy, so we’re using that now for many discussions. However there are times we want to make sure we have diverse representation in each group. We often will look to have representation from different areas of the company, from different locations, try to pay attention to things like the number of extroverts in a group, or how long people have been in the company. Most of the time groups are all doing the same activity and we bring back the results for everyone to see (usually this is written notes, but it could be a report or presentation). Last year at our 2019 retreat we did have three work groups doing different topics because we were trying to maximize brainstorming time. If you don’t have a mechanism like zoom to do the random selection for you, assigning in advance can also be a nice time saver. We chose last year to assign many things to make sure no one was left out, people didn’t have to spend time figuring out a group, and so that people didn’t always chose people they already knew because it was easy!

      I hope this helps, but do reach out by email if you would like some examples of what we did.


  2. I would find it very helpful if you could share some of the video’s or examples of how these activities actually look in action.

    Nicole Patrick
    • Hi Nicole! We didn’t really set up the activities and recordings to be for public viewing, however I’m more than happy to share additional details about particular activities. Just let me know which ones you are interested in. And if it easier, my email is

  3. Thanks for the post!

    Kevin Gacia