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What goes into an on-site for a remote team

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Wethos is a fully remote office with 20 (and counting!) teammates distributed across 16 cities, 11 states, and 3 countries.

As a remote team, we spend a lot of time on Slack and Google Hangouts. Getting IRL time together is a rarity, and while we live and breathe the remote life manifesto, it’s valuable to gather as a group to ideate and collaborate in the physical presence of our team. Outside of our semiannual meetups, we walk the talk of digital teamwork as a distributed team working across time zones, countries, and personal schedules.

At the start of 2020, we brought our team together for four days in Venice Beach, California, to set our goals for the new year, workshop initiatives, and simply get to know each other. We sat down with our Co-Founder and COO Claire Humphreys and our Operations Manager Jill Ettwein to gather their top insights for planning a successful on-site—not a retreat!—for remote teams. 


We call it an on-site for a reason: It’s about the opportunity to think and work side by side

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While most traditional offices call this type of event a “retreat” with the goal of getting teammates more familiar with one another, we wanted this time to be dedicated to work sessions and ideating on our company’s next steps. We don’t have an HQ, nor do we have any one place where most of us are located. Our home base is the internet and we only see our full team twice a year in person. Hence “on-site,” an opportunity for us to be in the same space at the same time, collaborating towards the future of our company together.

There are so many things that remote work enables teams to do, but the most difficult part is figuring out how to facilitate collaborative work sessions. We wanted the majority of our time together to be spent working side by side rather than giving presentations. With work sessions, everyone is up and about, sticky notes in hand, pitching ideas and talking through things face-to-face. It makes a huge impact when trying to solve tough problems.


Invite your whole team to answer the Big Questions

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Everyone got the opportunity to get up and share their ideas—not just the directors. Every person no matter the title brings a new perspective. Diving into 2020 planning, we knew there would be a lot of blockers and wanted the entire team to suggest ways our company can experiment with solutions. Someone in Product could have a great idea for Marketing and someone in Operations could have a useful tip for Sales. 

It’s invigorating to take people out of their own departments and challenge them to solve problems across the entire company. When cross-functional collaboration is invited into the process, people with different areas of expertise will approach problems in distinctly different ways. Making sure a broad variety of perspectives is involved allows for more creativity, and ultimately better solutions to our problems.

Handing over that amount of agency allowed our team to hit the blockers head on. Why bring on a team that you don’t trust to make these decisions? This level of ideating shouldn’t be reserved for just the founders. After all, we’re founding this company together. 


Make space for one-on-one interactions

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People were encouraged to request one-on-one time with someone else on the team. While we have a strong “cameras on” culture and will often see each other’s faces during our all-staff meetings, it’s nice to have face time with someone, especially if there’s not much overlap in the day-to-day. Nothing replaces going on a walk with someone or sitting together with lunch. It offers more connection than the 15 minutes of a work meeting, where the focus is on staying aligned with an agenda or making sure the internet is working.

These moments also came naturally as we made sure there was time for the team to get to know each other. As much as we were focused on getting work done, we were also focused on cultivating a space for people to interact freely. Whether it was scootering to and from dinner or relaxing on the rooftop, we wanted people to know their teammates not as who we are at work, but as who we are outside of our titles at Wethos.


All the little details matter big time when it comes to individual needs and preferences

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We often can’t know what people’s lives are like because we’re remote. It’s important to budget enough time to give people space. Naturally, personal time is important in this kind of environment. Sometimes people need to decompress from the day, call their family, take a shower, or read a book. It’s critical to give people the freedom to do what they want when there’s downtime.

Since we’re all typically working from our own homes, we’re extra sensitive to our remote teammates’ needs and preferences when they travel. We offered our team the option to either be in a shared Airbnb with others or stay in their own hotel room. This also includes asking about dietary preferences or restrictions! Make sure your team knows you are there and that you want them to feel welcomed and comfortable.

Spreadsheets were a throughline from start to finish. We had one master spreadsheet for the entire on-site that included, among other priorities: travel details, lodging information, meal times, and work sessions. Choosing restaurants ahead of the on-site and asking people to note their preferred orders saved time later on. Let’s face it: Keeping people well-fed always makes for better meetings.


Plan engaging, collaborative work sessions. Here are two exercises from our on-site!

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Creating personas to better understand and visualize your audience or community is a hands-on way to get everyone on the team thinking about who’s on the other side of your work. Have your team break up into pre-assigned groups to make sure people are collaborating cross-departmentally, and ask each group to work on a specific persona. Have them imagine an entire life for their persona, including hobbies, dreams, professional and personal dreams, and social networks.

The Crazy Eights exercise can be helpful when you want people to ideate quickly on a theme, with the focus being more on quantity rather than on quality. It involves drawing eight sketches in eight minutes and asking team members to share their top three sketches to wrap up the exercise. Asking people to draw also challenges them to visualize the solutions they would like to propose to the team. At the end, everyone gets sticky dots to vote on their favorite ideas from across the whole group.


Have thoughts on things we missed, or should consider?

Shoot me a note at [email protected] or hit me up on Twitter and share your perspective. I’d love to hear your thoughts.

CategoriesWethos News
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An Uong

An Uong is a writer living between Los Angeles and New England. In her role as Community Manager at Wethos, she strategizes around initiatives and partnerships to bring engagement, resources, and new learnings to the Wethos network.