September 22, 2020

How This Tech Company Held Their Quarterly Retreat Online

Geoff DiMasi

Inspired by connections and motivated to find a better way in all things, Geoff DiMasi is the Chief Partnerships Officer at Apostrophe.

From the start, ApostropheCMS has been distributed on purpose. We are a “remote” company by design and our team is distributed across the US and Europe. For us, that is rooted in our goals and values:

  • Our open-source CMS software tool is used around the globe. Being distributed allows us to build connections with people and support users in different time zones.
  • We can hire people that already use Apostrophe regardless of their physical location. This allows our future team members to maintain their roots in their community, or to have the flexibility to move when and where they see fit.
  • We can hire more experienced and diverse people more easily. Talent is all around the globe, and that opens up options for both parties.

Before making this choice, we talked to a lot of people and read many articles on how to make a remote team work. Anyone that has looked into these practices has likely seen the advice that remote teams should make it a point to gather periodically. Usually, that equates to some type of quarterly, twice a year, or annual in-person retreat.

That advice made sense to us, so we quickly got into a rhythm of gathering quarterly as a team. I can tell you from personal experience, it is good advice. There is something about spending a little time together that helps grease the relationship wheels and support improved interactions during remote work time. There are also conversations that happen between the planned sessions that can lead to problem-solving and other creative actions that are not on the agenda. And there is just the (perceived) ease in brainstorming and facilitating big-picture planning in person.

Enter COVID

Like many teams in all corners of the world, we had to come up with a new plan for our quarterly gathering. For us, this is our Assemblée, where we do strategic planning sessions for our OKRs (objectives and key results — a collaborative goal-setting framework), company updates, and team building. We did miss getting together, but through careful planning, we were able to do some very efficient and inclusive strategic planning while still finding a way to have fun together as a team.

Get a prebuilt OKR template from MURAL and collaborate to set your team’s objectives and key results:

Objectives and Key Results Template

The remote collaboration challenge

One of the first things we needed to figure out was how we were going to do those collaborative planning sessions that previously included lots of colorful sticky notes, Sharpies, and a timer. You know the drill: write down ideas on stickies, cull them, organize them, and then present them to each other — in person. We needed a way to pivot this experience digitally and still maintain the value of the resulting work. Moving everything online, we wanted to try to keep the magic of minds and mouths working in the same room.

I have led in-person workshops for several years. There are some important principles I believe in and wanted to make sure we carried over to Apostrophe’s online OKR planning session.

  1. All voices: Everyone’s voice should be heard in a very specific and ordered way. In other words, every exercise specifically has time and space allotted for everyone to participate and contribute.
  1. Quiet time: It is important to give people time to think and write individually before sharing their ideas. This allows for all of us that have different thinking and processing styles to participate on equal footing as much possible.
  1. Welcome all ideas — including the crazy ones: Everyone should feel free to write down or propose all ideas that occur to them. Creating a space where people can think broadly is an intentional step in the process. Allow time for and encourage people to generate a lot of ideas. Some will be great, some will not, and some may be surprising as ideas are jotted down, one flowing from the next.
  1. Prioritize: I believe in creating time to cull and prioritize ideas both individually and collectively. This helps create team consensus about the ideas that bubble up to the top, as well.
  1. Make it actionable: It is important to capture the work in some way so that it can become actionable.

How we solved this with MURAL

Considering these principles, we decided to design an experience that leveraged MURAL’s digital workspace for visual collaboration to simulate an in-person workshop. Poking around the templates in MURAL, we were inspired to create a board that supported our process of individual thinking as you can see here:


We also created a process for culling, prioritizing, and having group discussions on that same board:


Going into the first workshop, there was concern that we wouldn’t fit everything into the 90 minutes we scheduled. Finishing on time in a group setting can be challenging enough without the added pressures of a fully digital environment, compounded by a new process for our workshop. But we finished on time, and there was consensus among the team that we were actually more efficient and effective online! One member of the team shared this in Slack after our first session:

“Hey, I thought yesterday’s workshop was very well facilitated ONLINE, thanks!”


By taking the time to build a process within MURAL that upholds what we value, we were able to build an equitable platform for everyone to think, to speak, and to get the outcomes we wanted. Over the course of the week, we ended up doing three sessions for different aspects of the business. We used the artifacts created in MURAL to set to-dos that we believe will help us achieve our strategic goals (OKRs) this quarter.

Making it fun

Retreats are not just about the work. They’re also about that time connecting with each other. We decided to schedule two social times in the program. We knew we didn’t want to just hang out on Zoom. We have done that in the past and it’s okay, but scheduled casual interactions can often fall short when the same platform is used for regularly scheduled meetings. You can end up with some awkward moments, or worse yet, silence. In an attempt to avoid that, we hosted a trivia session and played 20 questions.

To make the trivia session more fun, I asked everyone to share something about themselves that they thought no one else would know. Not anything embarrassing ... just something fun! These amusing personal facts were one of the rounds. The other two were centered around food and beverage and technology. Seemed appropriate!

We used Kahoot!, which allowed everyone to respond to the trivia questions on their own phone. By doing it this way, we could still engage with each other across screens without having to jump in and out of different platforms in the same window. Since Kahoot! tracks everyone’s scores as you go, it brought out some fun competition, and we all enjoyed getting to know each other through the questions.

The 20 questions session was the brainchild of our marketing director, Ashleigh Mason. She mailed everyone a hand-crafted packet so they had their clue in advance. She made us wait to open it until we played, adding a bit of anticipation to the game. It was a lot of fun to work as a team asking questions of the person who held the clue. It brought out everyone’s personality, and we all felt like we got to see another side of our teammates.


What we learned about remote collaboration

A big takeaway from the retreat was how important it was to plan for each session. Really, that goes for almost all aspects of being a remote team, but it is especially on display in mass collaboration moments like retreats. Being remote on purpose and with purpose is something I try to keep in mind each day. It helps us operate better and it keeps us from falling into lazy traps that can happen when you use in-person interactions as a crutch.

Will we gather again in person when the COVID-19 quarantine restrictions are lifted and it’s safe for our team? You bet we will! We enjoy each other’s company and know that gathering has unique benefits.

But we have already said that we will still use MURAL even if we are in the same room to do our planning session (no more dealing with Post-its falling off the wall!), or we might do our planning sessions remotely in advance so we can optimize that time together in more creative ways.

Editor’s note: This post was originally published on apostrophecms.com on June 23, 2020.