Reflections from my remote team’s first in-person retreat

I’ve worked as a developer for Red Earth Design, Inc. since October of 2014 and, until recently, I had met only one of my fellow team members in person. Even though we have regular team meetings over video, and we chat on Slack, we were starting to feel like we could really benefit from an in-person retreat. Early in the summer, we decided that it was time.

Getting six remote team members together – who live in four different states and three different countries – was no small feat. It took a lot of planning and preparation, but on the day of the solar eclipse, the moon, the sun, and the Earth aligned, and our company converged on Chicago for the very first time. We spent two full days together, focusing on work activities in the morning and recreational or volunteer activities in the afternoon. You can read the official RED blog post about the retreat here.  Below are my personal reflections from the event.


Meeting everyone and hanging out together. It was fun to meet everyone after only interacting via computer or phone for almost three years. Our regular team video meetings gave me a good sense of what everybody was like, but there’s a certain je ne sais quoi that comes from actually spending time together in person. I think all of our activities – from exploring Millenium Park to eating deep-dish pizza to playing Pictionary – really helped us bond as a team and connect personally.

Working together. We tried to be strategic in planning our work activities during the retreat, focusing on things that would be a lot easier to accomplish in person than over a computer. One of our main goals was to get everyone up to speed on an improved workflow. I think it was a good choice of activities, as it was the type of thing that requires frequently looking over each other’s shoulders and troubleshooting. We also had a number of business-related discussions, which felt a bit more comfortable in person.

Staying together in a big house. In the early stages of planning the retreat, we considered the option of staying in a hotel, but it seemed too impersonal for a team retreat with only six people. So we followed the lead of other small remote teams and rented a big house through Airbnb. And I’m really glad that we did. The house was in Oak Park, a suburb of Chicago, and it was absolutely perfect. It was large, well equipped, and just a little bit quirky – with a full-sized mannequin in my bedroom. I especially liked the large dining table that we could all sit around while we worked. Oh, and the giant trampoline in the back yard was a nice perk.

Volunteering. Our company serves a number of nonprofits, and one of our core values is “making a difference.” So it made sense for us to spend some time volunteering as a team. I wasn’t sure how easy it would be to arrange a volunteer activity because many organizations require an initial orientation session. Because we were all coming from out of town, and we only had an afternoon available to volunteer, we needed something where we could hit the ground running.

Luckily, I contacted Ricardo at the Oak Park River Forest Food Pantry, and he was more than willing to accommodate us. He signed us up for a Wednesday afternoon food distribution shift, where we helped distribute food and carry out groceries for what seemed like an endless stream of food pantry clients. It was hard work, but I found it to be an extremely rewarding experience. And it was fun to see our team, for whom work is typically done sitting in front of a computer, perform the hard physical labor of schlepping heavy bags of groceries out to people’s cars.

Taking updated headshots. An underappreciated aspect of working remotely is that we’re constantly looking at team members’ headshots – whether in Slack or in Intervals, our project management system. Those headshots are often several years old, taken under poor lighting, and/or cropped out of a vacation or wedding photo. We decided that the retreat would be a perfect time to update our headshots.

Instead of hiring a professional photographer, I decided to borrow my dad’s fancy telephoto lens and pretend to be a photographer for a day. I took my photographer role very seriously, watching several YouTube videos on how to take a good headshot and reading several articles. This slideshow in particular gave some very helpful pointers. We took a lot of photos – both in our company t-shirts and in nicer shirts we’d brought, and we ended up with some decent headshots. Since the retreat, it’s been nice to see everyone’s updated headshot in Slack and Intervals.


The retreat was exhausting since we tried to pack so much into two days, but I returned home energized, excited about our team, and optimistic about the direction our company is headed. I like the freedom and flexibility of working remotely, but I think that periodic in-person retreats can be hugely beneficial for morale and productivity.