Hello! My name is Andrew, and I’m the Director of People and Process at Alley. I’ve been involved with the 2018 Alley retreat since last September, and I can’t believe it’s already over — well, almost over. My team is still finalizing all the expenses while I gather our retreat survey results so we can…. Wow, I’m even boring myself. From here on out, I’ll stick to the fun and interesting stuff.

We’ve all just returned from The Essex Resort & Spa in beautiful Essex, Vermont. Our entire team made the trip, some traveling 20 minutes from Burlington, and one team member traveling more than 3,000 miles from a remote island in British Columbia, with a leg of travel involving a seaplane.


Needless to say, it was good to get the band back together again. After an exhaustive search of potential venues across the U.S., The Essex beat out the competition for the third year in a row. That was decided back in February, so we’ll fast-forward a bit to August 12, the first day of the retreat.

A group of Alley team members standing in a circle at one end of a long green field with a gazebo in the background

We greeted our team members with swag bags upon their arrival. Everyone received a mug, a beach towel, a duffel bag, and socks (!) with our new branding. But wait, there’s more!

This year, our company reorganized into several scrum teams, each with a unique name and personality. Each team collaborated to create their own custom swag before the retreat. There were T-shirts, flasks, aprons, and pint glasses, all with customized branding designed and decided upon by team members. I expected flasks and T-shirts, but I was particularly impressed by the out-of-the box thinking with aprons. They’re a terrific culinary testament to our company’s commitment to innovation.

A large group of female Alley team members with their arms around each other standing in what appears to be a large wooden kitchen

We kicked off the first day of the retreat with sessions hosted by leaders of our Communities of Practice,. The sessions covered topics including UX/design and editorial practice, a QA workshop, Alley’s agile processes,  and a hands-on back-end exploration of WordPress’ new editor, Gutenberg. As a non-technical person at Alley, I thought it’d be fun to challenge myself with the Gutenberg session. I understood… none of it. But it seemed super interesting!

One of the standout sessions was hosted by senior UX developer Pattie Reaves and UX developer Shawn Cook. Their activity challenged our team to make sure every person at Alley had a buddy to help them escape New York in the event of a zombie apocalypse. At Alley, you can never be too prepared. People in the session were given a data set with the latitude and longitude of every team member, then had to sort everyone into pairs of geographically colocated colleagues. I was paired with my friend and principal software developer Jake Foster. Would we have fun escaping New York? Probably. Would we survive? Most certainly not.

A group standing in a circle next to banquet tables in a large white room

The sessions were followed by a State of the Company address by our CEO, Austin Smith. He showed us a TEDxHGSE talk by Amy Edmondson about Psychological Safety on Teams. Edmondson discusses the importance of establishing a safe environment that fosters speaking your mind, being creative, and collaborating on decisions without fear of being singled out for making a mistake. As a follow-up, Austin gave us an activity based on the mock Mars Mission HI-SEAS VI: If you were on a mock mission to Mars with those sitting at your table, what protocols, roles, and boundaries would you put in place to survive and function as a team?

A crowd shot of the Alley team sitting at many banquet tables in a large white room with chandeliers, watching a White man in a blue shirt give a presentation with a projected screen.

Once the terror of being stranded on Mars faded, our table got to work. We discussed how we would probably institute the Scrum framework to manage the operations of our Mars camp. We determined that we’d split up tasks so that chores were evenly distributed among team members. We talked about establishing rules and a specific strategy for conflict resolution. But the most important thing we discussed was boundaries, and how everyone needed their own personal space and time… to the extent that everyone might have to chill out outside in their space suits for a bit while each individual team member got the Mars camp to themselves.

When all the tables shared their results, “me time” and “personal space” were overwhelmingly a recurring theme. It seems like everyone here is more than qualified to work for a distributed company! Although given the choice, I’m sure all of us would readily give up our personal space to work together in a physical office instead of in a space tent 34 million miles away from Earth.

Five people standing and chatting in front of a window with a tree outside

We wrapped up the first day with in-person stand-ups with our scrum teams to plan out the next day of work. After that, the party began. We all loaded onto a bus and headed out to downtown Burlington, where we had dinner at The Farmhouse Tap & Grill and sampled (some several times over) their generous selection of craft beers. After dinner, some set out to play arcade games at The Archives, while others sang karaoke. Thankfully I haven’t seen any videos posted in Slack of Alley colleagues singing “Don’t Stop Believin’” at the top of their lungs. I hope none exist. It’s been done. We’re more innovative than that.

A selfie of many team members on a bus smiling and waving their hands

On our last day of the retreat, we conducted scrum-team working sessions. Each scrum team got together and worked in real life, in real time, in person with their scrum team. Why so much emphasis on the in-person, real-time, real-life aspect of it? Because we’re a distributed company, and this is the one time a year we get to work a few feet away from one another instead of over a Zoom call to Australia.

Team members holding a frisbee and talking around a white banquet table

With the psychological safety activity fresh in my mind, it was fascinating to work in real time with my team and pick up on mannerisms and communication styles that can sometimes be lost in Slack or on video calls. My team used this opportunity to be vulnerable and discuss our strengths and weaknesses. We wrote out a list of areas where we excel and where we can improve, and put together a plan to help our team become more T-shaped (excelling in one area, but knowledgeable in many). We’ve loaded these items as kaizen stories in our Jira product backlog, so we can continue to improve throughout the year.

We wrapped up the retreat with final remarks from Austin. Fresh off the recent arrival of his second child, he read us Gerald McDermott’s An Arrow to the Sun, a children’s book about a Pueblo child who is shot to the sun to meet his father and must prove to him that he’s his son by enduring a series of trials. After he proves himself to his father, his father shoots him back down to earth to share what he learned from his experience.

A White man in a red Alley shirt talking to a large group of seated Alley team members

Austin used this story as inspiration for us to think about our own narratives: our individual personal and professional journeys, our team’s journeys, and Alley’s journey. With psychological safety as the theme of the retreat, he further asked us what we would change about each of these narratives, and what’s holding us back from making those changes. Each of us wrote down our answers and shared them with our teams.

To be honest, it was uncomfortable at first to be so vulnerable. The shared vulnerability of the people around me encouraged me to speak openly, however, without fear of making a mistake, and share what I thought with the team. I can already feel how this vulnerability with my teammates has helped us establish a sense of trust, teamwork, and even greater psychological safety on our team.

Once the activity was over, we ended the day by bringing out a birthday cake for Valentin Cucu, our communications manager, who was an invaluable asset to our retreat planning. But the candles set off the smoke alarm and the entire resort was evacuated for about a half hour.

A White man holding a brown cake with lit candles in it and presenting it to a White bearded man with glasses

For real.

A fire truck with a long ladder fully extended to reach the top of the building next door while a White man with a red Alley shirt and blue shorts walks in front

Without a doubt, the retreat was a success. It was so incredible to spend time face-to-face with such fascinating and intelligent people who I spend every day with, but usually over the internet. Catching up with them, meeting (and most certainly exceeding) the company’s bar tab minimum, and making a sizable dent in the total beer and frozen pizza supply of the United States of America was an experience I’ll never forget.

A close up of the rocket ship logo and Let's Do Launch. on the back of the Alley T-shirts with a fire truck out of focus in the background.

I can’t wait until next year. Let the planning begin!

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