Our First Virtual Company Retreat: Key Learnings

Kaylie Boogaerts
Supertab— Behind the scenes
7 min readJun 1, 2020

In our previous blog, we explained how we went about setting up our first virtual retreat. This blog is all about what we’ve learned from organizing our very first remote AllHands and what we would do differently if we organize a remote AllHands again. (Although we really hope we can meet up in person in about half a year! 🤞)

Want to know what the team thought? Ask them!

After every AllHands, we ask the team for feedback to improve and make the next retreat even better. That was no different for our first remote AllHands. We asked the team the following question:

0 = “It was a disaster” and 10 = “It was set up perfectly!”

The average result is 8.1/10 — not too bad! Additionally we also asked for more specific feedback about the setup, schedule and sessions. Here are the main pieces of feedback and what we’d do differently:

The Feedback

Schedule

The timing of the schedule was well received. The team appreciated that the AllHands time slot of 1200–1700 UTC took into account both the EU and US teams. They also appreciated that social time was explicitly added to the calendar as this gave a good “excuse” to hang around and socialize without feeling the pressure to get other work done. The team also let us know that the amount of sessions was enough and we definitely didn’t need full days for a virtual AllHands as it can be quite exhausting to attend these sessions virtually.

Something I was personally worried about was timekeeping. This is already tricky at our regular AllHands and I expected it to be even trickier now because you can’t give as many visual cues during the sessions to the people facilitating the session that their time is almost up. At LaterPay, we’re all about being transparent and setting clear expectations, so here’s what I did: During our AllHands kickoff session, I went over a couple of house rules and I added one about time keeping. The rule was that I would interrupt whoever was speaking 5 minutes before the end of the session and asked that they please not be offended if I were to do so because I’m not trying to be rude, just to keep time. Time keeping overall ended up going pretty well, and this was also reflected in the feedback. This will probably be something that we’ll actually continue doing at physical AllHands as well!

Some less positive feedback that came up multiple times was that because the AllHands slot was only half a day, and we had set expectations to do some non-AllHands works before or after sessions, people felt pressure or personal desire to get other work done and had long, tiring and stressful work days. For multiple people in the team, it was a very intense week and they said it’s much easier to focus on the AllHands when we meet in person.

So what would we do differently? It’s hard to say what would be the perfect solution, but here’s what we’ll definitely consider if there’s a next remote AllHands:

  • Be more proactive in (over-)communicating that we recommend to avoid meetings outside of sessions during AllHands week and to already check calendars and recurring meetings during the AllHands week. This gives the team more flexibility on how they use their work time outside of the sessions and when they start or end their day.
  • Encourage (or even facilitate) discussions on how the expectations around how much work will be done, change during the AllHands week. When we have the AllHands in person, we have full days of sessions and don’t expect the team to do other work (except when absolutely necessary). This enables the team to be 100% involved. So we have to figure out what this looks like for half day sessions so that everyone can comfortably be 100% engaged with remote AllHands.

Sessions

Surprisingly (or not surprisingly at all?) the most appreciated sessions at our remote AllHands were the same as at our physical AllHands: interactive sessions and lightning talks.

Interactive sessions keep the team engaged and keep things fun. These are sessions that are anything but just a presentation. They can be brainstorming sessions, workshops with very regular input from the team, workshops where the team is split up into smaller groups and work through an assignment, or an AMA (Ask Management Anything) session. It’s very hard to only hold interactive sessions, but we set an expectation with anyone who ran a session to keep the presentation part high-level and leave more time for the Q&A portion. Questions not only engage the team, but also let the presenter know what topics/areas/directions the team is more interested in and want to know more about.

Lightning talks are a team favorite at every AllHands. Lightning talks at LaterPay last a maximum of 5 minutes and can discuss any topic and be presented by anyone in the team. After 5 minutes, there’s a hard stop, whether you finished your talk or not. They’re not interactive, but they are engaging as they’re usually about funny topics or more personal topics. They give us a glimpse of who the person is outside of their work or who we see on a daily basis.

The topics of our Remote AllHands’ lightning talks.

Tools & Social Interaction

Let’s start with Zoom. We’ve been using Zoom for meetings for a long time already, so it was an easy decision to also use Zoom as our “main conference room” for our remote AllHands. The team already knows how to use it, everyone has an account already, and we could make one “main conference room” Zoom link to reuse for all our AllHands sessions. Easy!

We used the Zoom breakout rooms feature for the first time and it worked great for workshops, although we struggled a little when we had (1) predefined groups to break out and (2) team members who dialed in with their phone. We quickly figured out how to deal with these challenges and everything went smoothly from there.

Pragli is the tool we used to encourage the social aspect of AllHands: chit chatting during breaks, while eating etc. The general feedback here was that using Pragli as virtual rooms (with video and audio) was a great idea and it encouraged conversations. In practice however, it doesn’t come close to actually being together and the tool is very new, which resulted in issues for some users that made it less likely for them to hang out in Pragli.

Another challenge we had with Pragli was the tendency for lots of people to gather in one room, which made having conversations hard. The reason why we went with a tool like Pragli was so that people could easily split up into smaller groups to chat. It turned out that in practice, this was a lot harder than expected. Imagine you’re chatting with a few people, and a few more people join so that the group becomes too big to have everyone engaged in the conversation. If you’re all physically together, it’s very easy to split into smaller groups so that the conversation flows naturally and everyone has a chance to contribute. Virtually this doesn’t come naturally as you have to make a conscious decision and effort to leave the room and enter another room.

What would we do differently? We’ll definitely keep Zoom as the “main conference room” and we’ll re-evaluate how we can encourage the social aspect of AllHands virtually. Pragli is a very new tool and it may have major improvements in half a year. We may also look for an alternative tool. The key will be that it has to work well for everyone from a technical perspective and it’s easy to use. I imagine we’ll still want a tool with different rooms and the challenge of groups becoming too big for conversation to flow naturally will remain. To solve this, a team member suggested to recommend the team to split up into two smaller groups when there are more than 5 people in one room.

In summary, a virtual AllHands cannot replace a physical retreat, but it was a great first virtual event for LaterPay. Setting clear expectations and over-communicating is still super important, perhaps even more so at a virtual AllHands. Pragli was a nice touch and added that human/social aspect, but there were a few issues with it that resulted in limited uptake.

If we can’t have a physical AllHands at the end of the year and we do another remote one, we plan to put extra effort in:

  • Setting clear expectations about non-AllHands work
  • Encouraging interactive sessions (over pure presentations)
  • Choosing a tool that will add the social touch to our remote AllHands and defining a recommendation to split up into smaller groups when there are more than for example 5 people in a room.

We’d love to hear from you if you have turned your company retreat into a virtual company retreat and what you would do differently next time, or if you have this challenge in front of you right now and you could use some help figuring out next steps.

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