Since Alley’s founding in 2010, we have evolved into a fully distributed company with nearly 70 team members spread across the United States, Canada, and Brazil. While we’ve learned to mitigate the challenges of working remotely and pride ourselves on having a strong work culture, we feel it’s critical for everyone to have the opportunity to be in the same physical location and meet face to face. That’s why we host company retreats, where we use group sessions to work together, share experiences, and have fun in ways that you simply can’t over a Zoom meeting.

In 2019, we decided to try something a little different. When Alley fully adopted Scrum last year, the company restructured into several cross-functional, self-organizing teams. So this year, instead of the company-wide retreat, we decided to have team retreats. These smaller gatherings give each team an opportunity to bond with one another in person and work to foster a healthy and supportive team dynamic. We’ve had a very successful year and have hired many new team members – so for many, it will be the first time meeting one another face to face! We still plan on hosting company wide retreats in the future, but we think that adding team retreats into the mix will also help build culture. We plan to document every team’s retreat and have teams present the exercises and team building activities they found most effective with the rest of Alley.

Heading to DC in March of 2019, Team Delta was Alley’s first team to take a retreat. Ivana Wong, Senior User Experience Designer, loves event planning and naturally chose to be the team’s retreat captain. Fortunately, both her and Susan Finkelpearl, Alley’s Director of User Experience and Delta’s Product Owner, live in the Washington DC area.  By having the rest of the team come to DC, they were able to use their local knowledge to choose interesting activities and restaurants.

The first day of the retreat was devoted to working together. For this, Ivana booked a conference room for the team. Finding an available conference room or coworking space can be challenging depending on where teams decide to retreat. At a minimum, all that is needed is a quiet space with good light and a decent internet connection, but it’s important to consider other amenities such as coffee, tea, water, and snacks. They spent time on client work as well as internal team work, such as coming up with ways of implementing Kaizen, or the practice of continuous improvement. This was much like any working day at Alley – except team members were in the same room together.

The second day of the retreat was reserved for team-building and fun activities. In the early stages of planning, Ivana created a survey enabling each team member to provide input on things to potentially do and see. With a various range of interests and hobbies across the team, it was especially important to let everybody weigh in on their ideas for a fun and productive retreat. See the tourist attractions or go where the locals go? Eat at a fancy restaurant or check out a dive bar? Team Delta ultimately decided to test their team cohesion at an escape room, followed by bowling at Lucky Strike. They also managed to visit the Smithsonian National Air & Space Museum, the Supreme Court, and see a Washington Capitals hockey game!

While the benefits of team-building exercises and working together in the same space are clear, the team retreats also present unique challenges. In order for a team retreat to be planned and executed effectively, teams must be stable. Team stability means, for Alley, that a team cannot have any kickoffs or launches scheduled for the desired retreat timeframe, and new team members have not just joined the team.

For Team Delta, the latter point regarding team stability was a factor, as two brand new team members were just recently onboarded. In Ivana’s words, Delta lucked out as the two new members quickly fell in with the rest of the team. If anything, she said, the retreat accelerated group formation and team stability. To this end, they used a portion of the working day to update the “Team Agreement” – an internal document that each Scrum team at Alley creates outlining the values, goals, and principles of the team.

The retreat sounded like a success on every front, so we asked Ivana for any pro tips she might share with the rest of Alley’s retreat captains and anyone else planning a similar retreat. She recommends that all captains create a guide that includes a detailed itinerary along with a general FAQ to capture questions that multiple team members are likely to have. She also recommends to check the weather and be ready to adapt for the unexpected! We also asked if there was anything she might have done differently. She told us that with so many work sessions and activities crammed into such a small amount of time, it’s important to factor in time for breaks and personal space. Equally important is to not underestimate the amount of time lost to transportation and logistics. She recommends factoring in a break time just before each dinner, to give team members a chance to unwind and relax on their own before evening activities begin.

The next Alley team retreat is planned for late April, when Team VIP is going to Sedona, Arizona! We’re looking forward to hearing about this retreat and we will be publishing a recap of their adventures in the weeks to come. If you’re interested in learning more about our approach to remote work, check out our latest ebook, Welcome to the World of Tomorrow!

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