Remote Team Retreat: The Details!

A remote team retreat is important for team cohesion.

RED is a remote team. Each team member works from where he or she lives, and we communicate over email, Intervals, which is our task management system, Slack for catching up in a chat, and Zoom for regular video calls. Team members are hired after phone and video interviews. Most of us had never met in person. But after a few years, it felt like the right time for us to meet up “in real life.” So the RED team decided to hold our first remote team retreat in August 2017. We planned the date, the location, and the agenda.

Kimberly, Ryan: Red remote team retreat 2017What happens at a remote team retreat?

Work. Play. Communication. Our planned agenda included workshops, recreational activities, volunteering, and more general discussions about the direction of the company. Here are some of the things we did:

  • We had a workflow workshop to perfect our processes.
  • We shared meals together.
  • As a recreational activity, we decided to visit Millennium Park in downtown Chicago.
  • We had some co-working time, where we worked on projects alone or in smaller groups, but in the same space.
  • Pictionary!
  • Emma presented the State of the Business report, and we discussed it together.
  • We volunteered at the Oak Park Food Pantry.
  • We shared our goals for our own professional development.
  • We took headshots. Jamie has mad photography skills in addition to her developer skills! Check out our new headshots!

Since this was our first time planning or experiencing a remote team retreat, it was a learning experience for us all.

Emma, Kimberly: Red Retreat 2017What was the most enjoyable part of the retreat?

Ryan: Volunteering was an uplifting activity to do together. We volunteered at a food pantry nearby, carrying food out to patrons’ cars. Since serving non-profits is a key element of RED’s values, this was a great way to put that into action in a different way than we usually do.

Kimberly: Being able to discuss our workflow process in person, and improve it, was very useful. We made progress more quickly and easily than we might have when we were all separated. Playing Pictionary with the team.

Pro tip: If you get to choose the word to draw, don’t pick “ulcer.” Diagnosing a stick figure is difficult!

Emma: Making in-person connections. Conversations over video are great, but interactions that happen in person lead to more trust and understanding, and it’s faster and easier to teach and learn from each other. We had a great time playing Pictionary! Games can’t be discounted for their power for us to connect and share together.

Jamie: We discussed the business itself, and we felt more comfortable making remarks in person versus on a video call.

Alisa: Meeting each other in person added another dimension to our relationship. I am an extreme introvert, and won’t even mention the fear of flying, so this was a real challenge for me, but it was nice to work and laugh together.

Pro-tip: Boxes of Pictionary, Taboo, Balderdash or other similar cards will get you flagged for a Super Special Search by TSA.

What aspect of the retreat do you think was most important for team cohesion?

Emma: Overall, just balancing enough work time and non-work time together. Sharing a house allowed for flexible timing and unhurried interactions, maximizing the quality of the short time we had together.

Kimberly: The workflow workshop. We all worked together on the steps and taught each other different aspects.

Alisa: I think working together on workflow, playing together, and volunteering together all played a part. Even just walking around downtown Chicago together was fun.

Ryan: I’m the newest member of the team, and meeting everyone in person just confirmed that this is really a team I’m happy to be a part of.

What would we change next time?

Red Retreat 2017Jamie: We might change the length of time the retreat lasted. We had two full days, one evening, and one morning. We crammed in a lot of activities in that time, and spreading them out further might have been better.

Emma: Maybe we would add a day so we could have a slower pace with more down time as well as more work sessions.

Kimberly: Honestly, I thought it was all great.

Any thoughts about the logistical aspects (travel, housing, transportation)?

Emma: Sharing a house where we each had private space along with lots of common space to share work and meals together was ideal. A hotel would have felt isolating and would have been more expensive, too.

RED retreat trampolining
The best part of the retreat for Emma and Jamie.

Kimberly: The housing was incredible and so perfect that it was close to all our travel locations.

Alisa: The AirBNB was perfect, both in its size and its location.

Ian: The house had a trampoline! It was perfect!

When should we do the next one?

This is up in the air! We all enjoyed our time together, but some of our extroverts would like to meet up twice a year, and our extreme introverts would be cool with every 20 years. We’ll probably shoot for something in between those two! More seriously, we’re considering once every two years.



Has your remote team done a retreat?

Are you considering one? Let us know your experiences! Or do you work in an office, and find this whole concept baffling? We’d love to hear any questions you have, too! Join the conversation below the photos.


Like it? Share it!


Alisa Cognard

Alisa was one of the first team members to join Red Earth Design, Inc. in early 2004. From data entry, she progressed to MySQL database manipulation and PHP coding. Alisa is responsible for all kinds of odds and ends: installing new websites, adding features to them, programming databases, PHP coding, website troubleshooting, website security, and organizational tasks for Red Earth Design.

Leave a Reply

Your email address will not be published. Required fields are marked *