What We Learned from Planning Our Biggest Retreat Yet
Working for a distributed company comes with some major perks, like working from home, flexible time off, and the freedom to balance your life in a way that works best for you. But of course it has its downsides too. It gets lonely. You miss your team. You miss those face-to-face “aha!” moments. Collaboration doesn’t quite have the same oomph when it’s face-to-screen. So as a way to get us together, the 1SE team puts on two main retreats every year, with a few mini retreats sprinkled throughout. For our all-staff retreats, one is usually in the US and the other is international. For this retreat, we had to settle on a location that was stateside, relatively accessible to international team members, and that offered plenty of activities, eateries, and workspaces.
Planning the Trip
Our past retreats were located in Mexico, Canada, and Indianapolis. Now, we can finally check Portland Oregon off our list. As a native Oregonian myself, Portland has always had a special place in my heart, and I was excited to show it off. The team started planning around 4 months in advance, starting with hotels and flights and after those details were set, we began researching and diving into the details. We wanted to find a good balance of food, fun, and outdoor time. I thought I had a pretty good sense of everything that Portland had to offer, but I learned a TON along the way.
We wanted to pick a time of the year that most people could make it. Juggling schedules can be a demanding process, but we were happy that the majority of the team were able to make it. We planned the trip to coincide with the World Domination Summit, a 4-day conference geared towards goal-setting, inspiration, and creativity. The dates were set, June 26th-July 5th. It was an added bonus that the team would be together for the 4th of July. For a few of the team members, it was their first time in the US, so you can imagine the fun we had showing them the ropes on our country’s big day!
We wanted to start the week off strong, so we planned most of our work-related meetings right up front. The idea was to front-load “the important stuff” so if last minute changes happened, we would have time to adjust and shift the schedule around. The team arrived on Wednesday and our biggest meeting days were the following two days. We set up shop in the downtown location of WeWork, which was the perfect accommodation for our team—complete with cold brew on tap and a ton of other amenities.
We scheduled the first few workdays from 10am to 6pm, with meetings sprinkled throughout. We even sent out an agenda beforehand to make it easier to plan ahead, squeeze in leisure time, and run errands if needed. During the week, we kept most evenings open aside from our company dinners and team building events.
After a day of meetings on Thursday, our first dinner together was at Andina, a Peruvian restaurant in The Pearl. Not only was this the first meal we shared together as a team, but for some this was the first time meeting face-to-face. We booked a private room in the bottom floor in a cozy little wine cellar style room. It had the perfect feel to it, big enough to accommodate our group, but the room was cozy and we were able to talk to everyone and enjoy catching up. I’m pretty sure we ended up ordering one of everything—we let our server pick the restaurant’s “can’t miss” items. It was such a delicious meal and I highly recommend if you’re looking for accommodations for a small group.
We wanted to do something less formal and intimate, so after a long workday on Friday, the team ventured across the river to my house where we enjoyed a BBQ dinner together in the backyard. It was the perfect way to end the work week and helped pave the way for a weekend of fun activities and some much needed downtime.
On Sunday we had the pleasure of visiting one of our favorite 1SE users! Heather Champ has been using the app for years. She posts her compilations each month, and they almost exclusively star her gaggle of farm animals. Heather lives just outside of Portland, so we piled in a few cars and made the trip to go visit and see her now infamous baby goats. After learning about each of the goat families, feeding the babies their lunch, and meeting some chickens, we wrapped up our visit with a final group photo. Thanks again, Heather!
We’re lucky enough to have users from all over the world and we’ve been thinking about ways we can include users into our retreats. We loved this opportunity to meet one of our longtime users, so we’re hoping to incorporate this again for our next retreat. A 1SE meet-up perhaps?
After our last day of meetings, we had a special farm-to-table dinner out at Kruger’s Farm on Sauvie Island. The evening kicked off with a tractor ride out to the marionberry fields. We picked berries and walked through the fields, mesmerized by the rolling hills and farmland. The weather couldn’t have been more perfect. It was a cool 70 degrees, almost golden hour, and you could smell the berries ripening in the evening sun.
After we had our fill of berries, we hopped on the tractor and were taken a little way down the road. As we approached, we could see a huge Oak tree and underneath a table set up for us. Along with the chef, bartender, and our server, we were the only ones in sight. It was a nice change of pace from our week of activities. Having that much space all to ourselves felt extra special after spending 5 days working together, planning our company’s next steps, and bustling around downtown Portland. The opportunity to get out into the fresh air and wide open spaces made this evening one of my favorite experiences of the trip. At one point, the conversation quieted, and I looked around to see everyone just listening to the sound of the wind in the oak tree. We didn’t have to say much, it was a silent agreement that this was exactly what we needed. After a few toasts and even a few happy tears on my part, we settled in for dinner.
After dinner, we played a few rounds of cornhole and took advantage of the golden hour lighting. We were even able to squeeze in some team headshots. All in all, this event was my favorite part of the retreat, a magical evening with fantastic company.
Our next adventure was a wine tasting trip in the heart of the Willamette Valley. We used Back Country Wine Tours and visited 3 wineries total. We didn’t have to worry about a thing, and our lovely tour guide Katie drove us across the rolling countryside and even provided a delicious lunch at one of our stops. We spent the day touring around and learning about what makes the Willamette Valley such an abundant and bountiful area for wine.
The future of 1SE Retreats
Our last meeting in Portland was all about brainstorming the next retreat. Each team member got to throw out their own ideas, and it was a fun way to get people excited for the next retreat. In the month that has passed, planning has already begun. We’re looking at a few dates in February or March, and right now we’ve narrowed it down to 4 locations: Japan, Costa Rica, Mexico, and Peru.
These retreats, while valuable for our team morale, are getting bigger and bigger and with that, more complicated to plan. We have 4 people on the planning committee, and after we narrow down our options, we’ll have a team vote. Based on those results, our CEO and COO will make the final call on location. Once the location is picked we plan on sending a couple of us on a “recruiting mission” to get a good feel for the area and start ironing out the details.
The New Year always brings a fresh set of challenges. Who knows how big our team will be by then? We’ll be taking a few key learnings from this trip and using it to plan our next.
- Hire a photographer. This was the first time we had someone join us solely to take photos and it made a huge difference. In the past, we relied on our own photography skills, but even portrait mode couldn’t save us. We want to focus on being together and bonding, not having to whip out our phones every 5 seconds. Hiring Olivia Ashton to join us and take the stunning photos above was a game changer. They turned out great and we finally got a decent group shot!
- Plan for plenty of free time and relaxation. The thing about retreats is that they are part work, part vacation. It can be stressful, especially on days where you have back-to-back meetings for a few hours. To help with traveler’s fatigue, we opened an account with a local sauna and spa called Knot Springs. Team members could enjoy the springs, book a massage, and even join in on some workout classes. The views from the springs were stunning with Burnside Bridge and the iconic Portland sign glowing from across the river. Worth. It. We hope to find something similar in each location we travel from now on.
- There will always be cultural differences to consider. Our newest team member, Dima, hails from St. Petersburg Russia, and this was his first time in the United States. Some of the many observations he made was that our sidewalks are huge, our homes are small (he only saw mine), and Americans have a weird habit of drinking water to accompany alcohol. That last one we had to have him to explain. Apparently in Russia, when you drink, you drink. How can you drink properly when you’re full of water? We thoroughly enjoyed hearing these subtle, not-so-suble differences, and I can’t wait for the opportunity to travel to more places with this diverse group of people.
- Once your team grows over 10, it’s harder to plan a retreat around a ticketed event or conference, in our case WDS. It was logistically pretty tricky to squeeze in meetings, activities, downtime, and fit in events from the conference schedule. If we were to plan this again, we would leave it out entirely, or make it more of an opt-in sort of thing.
- Plan for families and +1’s. This was the first retreat we allowed plus ones and it was such a lovely opportunity to get to know our team and their families. In the future, we’ll be looking into how we can incorporate family members into at least one of our retreats per year.
- Consider your flex spaces. For previous retreats we were small enough to book airbnbs. This time around, we booked rooms at Hotel DeLuxe and the accommodations were amazing. They had a lovely lobby and bar, but after gathering feedback from the team, we learned that people wanted more options for flex/hangout spaces. In the future, we’ll be looking at hotels and accommodations with flex space where we can hangout, visit, and have a little bit more casual setting for socializing.
- Team feedback is vital. Gathering information on what worked and what didn’t was the first step towards planning our next retreat. We sent out a survey to the team once everyone had settled back in after Portland and a few things became clear. First, that general accessibility is crucial. Our hotel was situated perfectly, it was walking distance to shops, bars, etc., and that seemed to be a huge bonus for folks. Another thing many members of the team mentioned was the co-working space. Since our hotel didn’t have a work focused common space, having our meeting rooms at WeWork really worked out for us. Here’s a snippet of some of the feedback we received:
“These retreats are invaluable. They give context to the team members behind the text threads. Our Portland retreat was so much more than just being able to work in a common space together. The small trips to get coffee…walks around town…boardgames and drinks in the evening…helped ground me in a deeper respect and appreciation for those I work with. I went to Portland to meet up with my co-workers, but by the end, I was hanging with family.”
— Jason Forest, Product Lead
We are so excited for the future of our retreats. Each one is different and poses its own set of challenges. We’re excited to see how these voyages develop over the next few years and can’t wait to document more of this process along the way.
Huge shoutout to Stephanie Lee and the team at Buffer. They have been a huge inspiration for our planning team—especially their in depth articles on their own retreat planning process. They have quite the undertaking when planning for a team of over 80, so we’ll continue to look to them for guidance as we grow.
If you are on a distributed team and have experience with planning company retreats, we’d love to hear from you!
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