Planning Our Remote Team Retreat
We started out reading articles from other founders (see below for a few of our favorites). We found these articles incredibly helpful, so we thought it would be fun to reminisce on our retreat here and pass along some additional inspiration and ideas.
- How to Run a Company Retreat for a Remote Team (Zapier)
- How and Why We Got Our Entire Team Together (SkyVerge)
- Step-By-Step: How We Planned a Retreat for a Remote Team of 75 (Buffer)
We could have waited a year until we had a bigger budget to work with. However, we knew the sooner we could spend time together in person, the better. We set our priorities early on, put the majority of our budget there, and got creative.
When it came to timing, we decided to plan it around a specific date. One of our clients, Moink, was being featured on Shark Tank . We knew it would be fun to watch the show together and celebrate the brand we helped create from day one. Waiting on the release of the air date meant that we couldn’t plan as far in advance, but the planning stars aligned and it worked for everyone’s schedule.
Many of our team members are working moms with young children, so it was important to us that we kept the retreat to just a few days. We opted for a Saturday - Monday.
Goals & Intentions
While we love the idea of remote team retreats that involve project sprints and the opportunity to dig into deep work together, walking away with tangible evidence of a successful retreat, we knew our goals would be different. We went into the weekend with three main areas of focus:
- Connection: Having face-to-face time is a rarity for the majority of our team. Building connection both intentionally and organically throughout the retreat was our priority.
- Creativity: We scheduled creative brainstorming time for key clients. Anytime you get a room full of creatives together, creativity is woven into the fabric of conversation, and we found there was no shortage of creative discussions and inspiration sharing.
- Rest: We believe rest and rejuvenation are crucial to both the individual and collective health of Well Refined. If we aren’t individually healthy, the team suffers. And if the team isn’t healthy, our clients suffer. And if our clients suffer, the world misses out on their best offerings.
When it came to deciding when the “right time” was for a first retreat, we decided it would be better to host a smaller-budget retreat sooner rather than a more expensive retreat later. We were eager to get together, and we’re so glad we didn’t wait.
A few ways we stuck to a conservative budget:
- Location: We selected a city based off where the most people lived. Since we have 3 team members in Raleigh, choosing that location meant 3 less plane tickets and no rental cars needed.
- Accommodations: There was a significant price difference between renting one single, large Airbnb vs. splitting up into two smaller rentals. We hope to have everyone together in the same space next time, but this was a sacrifice that was worth it this time.
- Activities: We didn’t plan extravagant activities, but rather focused on low-key time together. This fit in well with our rest focus.
Accommodations & Logistics
Airbnb for the win! It was crucial to choose one location with a nice-sized, comfortable meeting area for the whole group, After that, our priorities were proximity to downtown Raleigh and aesthetics. We’re a creative team, so design mattered.
While one location would have been ideal, for budget reasons we went with 2 separate homes. Originally we planned to split the group up according to who works together most, who sees one another regularly for client travel, etc. to give everyone a chance to connect. However, due to flights, a portion of the team flew in a day early, dictating the house assignments.
While we were inspired by other retreats that included project sprints and intense work sessions, our schedule reflected a commitment to the areas of focus we previously identified: Connection, Creativity and Rest.
- Morning: Finalize last minute details and stock AirBNBs with groceries and gifts.
- Afternoon: A portion of our team members fly in.
- Evening: Dinner near the airport at Babymoon Cafe with those in town.
- Final team members fly in.
- Breakfast at the main Airbnb with lots of hugs and “so happy to meet you!”
- Work Session 1: Enneagram Pairings. We met in small groups according to Enneagram type pairings and discussed the relevant pairing sections on work partnerships in The Enneagram in Love and Work.
- Lunch: First group meal at Sitti and introduction to One Conversation (see below).
- Work Session 2: TASC and Paint Done. We gave all of our team members Brene Brown’s most recent book, Dare to Lead, at part of their holiday gifts. Brene shares TASC and Paint Done methods for team assignments with the goal of clear communication and understanding from the beginning of any assignment or project.
- Work Session 3: Client Brainstorming. We selected a few key clients who would benefit from our face-to-face brainstorming, dreamed big for their work, and set plans in place for execution.
- Escape Room: Recommended by several of our team members, we rented out an Escape Room and made it out with 2 minutes to spare! It was super fun to watch everyone’s personalities (and paranoias) on full display. Let’s just say one of the quietest among us was the star of the show and one of our “fearless leaders” could be found in a corner, making no contribution at all. :)
- Dinner In: Everyone pitched in and cooked a Mexican feast. We enjoyed a casual dinner in and played the game Spark - an ignitor of soulful conversations. (Wand optional.)
Morning: Free time for rest, yoga, exploration, worship, a lazy morning, etc.
- Work Session 4: Agency Analysis and Brainstorming. Over Mellow Mushroom pizza and salads (a nod to the first meal Jane and I shared together), we spoke candidly and constructively about what’s working in our agency, what’s not, and where we go from here.
- Work Session 5: Dreaming. While we had the luxury of being together in one room, we dedicated a portion of time to talk through our dream clients and projects in detail. From the qualities of founders we would like to partner with, to the industries in which they lead, we got specific about what’s important to us individually, as an agency, and where we want to go from here.
- Impromptu Photo Shoot: We wanted to grab a fun photo of everyone with their individual signs, and then it turned into a full-out photo shoot where we were able to knock out new, consistent headshots for our team page.
- Dinner: Brewery Bhavana and One Conversation
- Evening: One of our clients, Moink, was featured on the Shark Tank episode airing this evening. What an experience to see a brand we poured so much heart into on Shark Tank! We worked alongside Moink’s founder, Lucinda, from the beginning, when the idea of Moink was just a seed.
I had the chance to join Lucinda in LA when the show was taped, where I also got to meet one of our influencers, Jenny Castaneda of Cook & Savor. She met us in LA to cook up the delicious Moink meat for the Sharks. Lucinda nailed the pitch, won the heart of viewers, and walked away with a deal! Back at the Airbnb we toasted with champagne and celebrated the gift of seeing such a strong, beautiful mission get national exposure.
- Early morning meeting with a local founder and current client.
- Work Session 5: Process Building. Working team breakfast at Morning Times to continue adding more structure to our services and processes. Following breakfast a portion of our team headed for the airport…lots of hugging and “see you soon!”
- Lunch: Quick lunch at The Raleigh Times where we all agreed that the weekend was pretty much perfect, and we were exhausted.
Afternoon: We headed over to HQ Capital Club (a stunning space!) for a founder meeting with Jesse of Fourscore Business Law. Jesse has been a client of ours since Fourscore was just a twinkle in his eye, and has also provided Well Refined with incredible legal support along our journey.
And with that, the remaining team members headed to the airport. Our first Well Refined Team Retreat was complete!
In keeping with our focus of Connection we ordered the game Spark to create space and fun around deeper conversations. We loved the game, but it turns out we didn’t really need it. Would be a great addition to your retreat if you’re hoping for soulful conversations, but not sure if they will come organically.
One of our team members used to work for Michael Hyatt and shared his One Conversation tool for the retreat. For the majority of our meals she organized this activity and everyone loved it. Not only did it create deeper, richer conversations, but it also kept everyone connected across the table and helped ensure that no one was left out just because they may naturally hang back in larger conversations.
We sent out a sign-up a few weeks before the retreat for favorite drinks, snacks, food sensitivities, etc. We made such each location was stocked with everyone’s favorites.
This was one of our favorite parts! It was important to us that our team felt loved and pampered, so we got creative…even with a smaller budget. Each team member received:
- Five Minute Journal
- Felt Letterboard (Complete with personalized, just-for-fun “job title”)
- A “gift card” to pick out one piece of meaningful Dear Mushka jewelry
We also made sure each bed had a small bag complete with travel-sized goodies and a note welcoming them to Raleigh.
What We Plan to Change Next Time
- While we hope to be together in one location for our next retreat, if we ever had to separate again we would prefer the two houses be closer together.
- While some of our team was in town for 3 nights, some were only in town for 2. We needed every bit of the time, so having the full 4 days/3 nights next time (including travel) would be helpful. Of course, longer would be better, but with a team that includes working moms with young children, a thoughtful balance is priority.
- Our last Work Session was detailed-oriented and required deep thought. It would have been better to knock that out earlier in the weekend when we our energy was highest.
In short, this is our encouragement to other founders - especially those with remote teams - to make a retreat happen if possible. We have learned from the hospitality we’ve experienced from our clients when we travel to them, and we were eager to pass along that opportunity for connection to our internal team. What started as a small “what if…” when we were just a team of 4 grew into a humble, yet productive and sweet, weekend together.
Cheers to YOU and the experiences you’ll create for your people!