How I Planned 1SE’s 5th Team Retreat
What I learned from planning my remote company’s trip to Lima, Peru
Early on, I knew the scope of this trip would far surpass previous retreats. As a remote company, we try to get the whole team together twice a year, and this was a retreat of firsts for us: specifically forming an official retreat planning team, doing a scouting trip like our friends at Buffer, allowing the team to vote on the final location, allowing plus 1s for employees to bring loved ones, and planning a non-paid excursion to Machu Picchu for folks interested.
This was my 2nd time planning our company retreat, and going from planning a trip in my hometown (check out that post here) to a full-blown International adventure was a huge jump. When you’re on a remote team, you often wear many hats. I’m 1SE’s Brand Manager and I specialize in marketing, social media, and strategy, but I’ve always wanted to travel more and flex my event planning muscles. So last summer, when we needed someone to own the logistics of our retreats, I volunteered. What I’m saying is, I’m a semi-newbie at this, but with the help of my planning team, which consisted of our two co-founders and myself, the guidance of VIPAC, and a few connections from the retreat planning teams from Buffer and Komoot (both remote companies), I was able to plan a trip that I am overall quite proud of. It takes a village!
Our Planning Timeline
Initial planning started back in July 2018 right after our Portland retreat. From start to finish planning lasted nine months. Since planning retreats is not my full-time position with 1SE, I was devoting anywhere from 5 to 15 hours a week to the project. Most of my time was spent on research, emails with our contacts, booking, payments, invoices, and negotiating contracts. Not to mention keeping track of dietary restrictions, emergency contacts, travel, etc. Phew! We used Basecamp and Google docs to keep track of everything, and I created a dedicated slack channel to post ideas and updates for the planning team. Here’s a general timeline of where we started and how we tackled the logistics for the retreat.
How We Decided on Lima
At the end of our Portland retreat, we had an all-hands meeting to brainstorm ideas for the next one. We took the team’s list of potential options, and by the end of the summer, narrowed it down to 5: Australia, Costa Rica, Mexico City, Japan, and Peru. Each of the members of the planning team took a location and broke down the general costs. We took the average cost per individual to fly, flight times, hotels, and co-working options—each of these being key pieces and what we deem ‘non-negotiables’ for a successful retreat. We quickly realized that Australia would be WAY out of our budget and WAY too complex, mostly due to the cost of flights and the insane travel times. The average flight time for the team would have been 23 hours. Yikes. No thanks.
The biggest piece of feedback we gathered from the last retreat was that people LOVED the walkability of Portland. When narrowing down the list, we looked into the major neighborhoods of each city—of our 3 potential locations each looked solid as far as walkability and getting around. Using surveys to gather feedback on what went right and what can be improved has helped steer our decision-making process for the retreats. We use this feedback as a Northstar when looking into options.
Our Founders had the task of narrowing down our options to 3 locations so that the team could vote. Once we had it narrowed down, I put together a document to present to the team, highlighting the neighborhood, culture, coworking spaces, and potential activities to give everyone a sense of each location. This was a fun document to put together, and if you find yourself planning a retreat for your company, I highly recommend including photos and visuals for your team to get a feel of each city before they vote.
After this presentation and discussion of the options, I sent out another survey and the team voted, ranking their first, second, and third choices. It was close, but the team decided on: Lima, Peru!
The Scouting Trip
This was the first retreat where we had a scouting trip for the planning team. This was a suggestion from Stephanie over at Buffer, who I had the pleasure of chatting with about retreat planning. I had seen one of her articles on her own experience planning retreats for Buffer, so I reached out, eager to get some advice. One of the first things we talked about was how important a scouting trip was to the process. She explained that being able to “get in the shoes” of the travelers before the trip even started gave her valuable insights into the planning process. We tried out different restaurants, toured coworking spaces, and attended local events and activities, trying to get a feel for the area.
The scouting trip was also where I started our shared google maps for the neighborhood. Check it out here if you ever find yourself needing recs in Lima! I used the map to pin fun restaurants, attractions, and parks for the team to check out on their own or with a group. I also used it for marking our hotel, coworking space, and labeling where our dinner reservations were located. The scouting trip helped me focus on the details, making sure that everything was set in place to set to run smoothly.
The unique thing about Lima is that it’s the birthplace of our Founder, Cesar Kuriyama. I was secretly hoping it would be chosen because what better way to get to know Cesar than to visit his hometown and get to know his culture? Not to mention, he had the inside scoop on the best restaurants and activities. Cesar’s input on the planning side was instrumental to the success of this trip. It added a nice personal touch as a whole and gave new members of the team a little glimpse into Cesar’s history.
Hotel, Coworking, and Logistics
Cesar’s family had recently opened a new hotel in the heart of Miraflores neighborhood called Libre Hotel. They had been open around a year when we first started looking into it as an option. When we arrived, it was love at first sight. It’s a smaller boutique-sized hotel but with all the amenities of bigger chains. Libre was perfect for us and had a gorgeous rooftop patio where the team gathered most evenings. Booking the hotel rooms was one of the first things we did once we locked down dates.
A massive component of planning our retreats is finding the perfect coworking space. We need a mix of casual and formal spaces varying in size. For some meetings, we just need space to sit and chat, and for other meetings, we need more whiteboards and projectors for the larger group. The work portion of our retreat is crucial since we don’t often get face time to sit down and solve complex problems or brainstorm as a team. When looking into coworking, we focus on walkability (from the hotel), enough space and meeting rooms for various size meetings and breakouts, and of course, reliable wifi and basic amenities like whiteboards and float desk space. We found Selina coworking a block from the hotel, and when we visited it on the scouting trip, it was perfect! The coworking portion was just opening up, but when we went as a team in March, it was the official grand opening — excellent timing and super fun to be around for the festivities.
Overall the experience was positive, and the space worked out great. We booked floating desks for everyone so the team would have 24/7 access via key cards and their common areas were quirky and quite charming. One of the rooms we booked was a big flex space complete with bar and projector, with colorful wall art from local artists.
The one major drawback to this space was there was no filtered water available in the coworking portion itself. Luckily, Libre hotel had water stations on every floor, so folks could load up and haul over water throughout the day. This was one of those details that you would never think of, but there you go, access to fresh drinking water! A basic thing, but crucial to keep in mind when traveling in places that don’t have clean drinking water from the tap. We’re spoiled here in Portland.
Planning Team Dinners and Events
There was no shortage of good food in Lima. In fact, there were sometimes too many options. On our scouting trip, we checked out a few places and were hoping for big private rooms for a few of our team dinners. We wanted to break up dinners so folks could have a good balance of structured and planned time together, but also enjoy the neighborhood and explore different places. We had a total of 3 planned dinners: our welcome dinner, our team-only dinner, and our goodbye dinner. The other nights we were on our own, but most of us would gather and go to a food court style place with a ton of options, or split off into smaller groups.
Our welcome dinner was at Huaca Pucllana, an archeological site located in central Miraflores. We planned it for Monday evening, and +1’s were included. The restaurant had a spacious open-air seating plan and views of the pyramid. We planned the next dinner at Astrid y Gaston, a lovely restaurant located in the San Isidro district. The restaurant resides in the Casa Hacienda Moreyra, an estate built in the 17th century. We booked their private room and did their tasting menu experience. It was incredible and the perfect way to get the team together and enjoy a delicious meal.
The final dinner we planned was our Goodbye Dinner at Panchita. Another great Peruvian experience and one we’ll never forget. It just so happened that the restaurant was participating in Earth Hour, an event that businesses opt-in to turn off their power for one hour. We had no idea this was happening until about 30 minutes into our meal. And what a surprise! All of a sudden, the power was shut off, and servers came around and lit candles on everyone’s tables. It was such an unexpected and fun treat! We were all pretty confused, but it was oddly calming and fun to eat your food with just candlelight (and the occasional cell phone flashlight) as your guide. This was quite the experience to wrap up the retreat.
Along with the team dinners, we had a few fun activities planned for the group. All were opt-in, which included an escape room, a visit to the chocolate museum, and if people were brave, paragliding! Some feedback we got from Portland was wanting a bit more free time, so for this trip, we made sure all the activities were optional. Looking back, I wish we would have had one or two team activities planned outside of the dinners. It’s all about balance after all! More about that below.
What I Learned
Overall the feedback from this retreat was really positive, but we always want to improve. Here are some key takeaways I gathered from the survey, some anonymous feedback, and odds and ends of what I learned throughout this process:
- Google Maps and Team Guide.
Putting together the google map for the trip and creating a trip guide was a gamechanger. It was a handy way to compile a list of spots to check out, note important places like the hotel and coworking, and offer up some suggestions on activities. The team had the opportunity to add to the map throughout the trip, so it ended up being a neat living document to look back on afterward!
I loved everything about this retreat! Thanks for making it perfect!!!
2. Trip Journals.
This was the first retreat where we tried out journals. The idea was to have a little keepsake at the end of the trip where everyone has a chance to write in other people’s journals — short notes, drawings, or funny memories. After we sent out the survey, we got feedback that it was a really nice way to connect with everyone in a different and interesting way. I loved opening up mine in the airport and reading the sweet notes left by my team members. We’ll definitely be bringing this back for the next one and see how it goes!
3. Balancing Free Time.
The overall feedback from this retreat was that the balance of free time was much better than previous retreats. Our retreat schedule usually follows the workweek of Monday-Friday, but for this retreat, we threw in a free day on Thursday to break up the week and allow for some much-needed downtime. Having a free day was clutch, especially after Wednesday, which ended up being our toughest day. It consisted of back-to-back beefy meetings.
Overall the retreat was excellent. Seriously, great job on all fronts. I feel like I had a bit more capacity for meetings and work, but Thursday off was nice.
All of the restaurants were outstanding, and we had a good balance of work, team bonding, and free time.
Planning our meetings has been one of the hardest balancing acts to get right. About a month before the trip, we reach out to the team and see what sort of meetings we need to schedule. This is always an afterthought for the planning team and something we need to keep at the forefront. A lot of the more negative feedback we got was about meetings. Many times we found ourselves rushing meetings to get through everything, so next retreat, I plan on sitting down with each department lead and really carving out time for each and being strategic about it. Our plan is to have an initial meeting, pitch our meeting ideas, and narrow down as a group.
Maybe we can have a better system beforehand of deciding what needs to be talked through and for how long to create the schedule, so that nothing gets left out and we don’t need to make last minute additions!
5. Arrival Times and Early Check-in.
Some folks arrived at 5 am, so we ended up booking rooms a day early so they could check in early without having to wait around. No one wants to arrive at their hotel after 13+ hours in the air, only to have to kill time before check-in. I highly recommend keeping a close eye on arrival times and booking rooms accordingly. This may seem obvious to the seasoned veteran at travel booking, but it was a detail that made a huge difference for me. It was something I had never thought about before.
I cannot begin to express my gratitude for you being on top of [my arrival]. when I got in, I was a zombie. I could not have coped with waiting to check-in. I would have wound up sleeping in a gutter somewhere.
6. Transportation from the airport.
In the past, we had relied on Ubers or taxis to shuttle people to their hotel upon arrival, but since the airport in Lima was so far away, we ended up hiring a private shuttle service through VIPAC. This was huge for us, and the team felt better about having a dedicated driver, than having to navigate taxis or ubers in a new country. The Lima airport is a madhouse, but the driver’s had our names and “1 Second Everyday” written on signs to make it super easy to find them. There was no thinking involved. It was perfect!
7. Welcome Gift + Local Currency Stipend.
Since this was our first true international retreat, we tried out a new way of handling stipends. Upon arrival, each team member got a welcome gift with some local Peruvian snacks, a power converter, and a cash stipend. This way, they would have some local currency to use right away. The team found this extremely helpful, and we’ll definitely continue this for next retreat!
You guys really nailed arriving in Peru. The transportation from the airport, to Emily and Cesar waiting in the lobby, to the thoughtful and considerate welcome bag (which EVERYTHING was put to use), the google map and even the printed itinerary….you guys just nailed it.
8. Dietary Restrictions.
I learned that I need to double, no, triple check everyone’s dietary restrictions and convey it to each and every restaurant. Especially for international trips, a ton of stuff can get lost in translation. We had a few hiccups at a couple of the restaurants where we had to ask for accommodations on the fly, but overall it worked out. Just a note to self…CHECK AGAIN!
9. Babies and Children!
This was also the first retreat where we allowed children and oh my goodness, this was such a nice addition. We had August, a tenacious 8-year old who was such a joy to be around, and our first 1SE baby, Amy! Having children around was amazing, especially to see our team members thrive in their parent roles. It allowed our team members with children to be at ease since their kids were so close by! For our Team only dinner, we ended up finding a babysitter for August, which worked out great, the rest of the time he drew or played Nintendo switch. Such a fun time and we’re excited to bring this back for our next big international retreat. I mean, look at that baby’s face!
10. Overall Retreat Structure.
Now that I have two major trips under my belt, it’s nice to compare them and see what worked and what didn’t. After the complexities of this retreat, the planning team has decided that we are going to continue with one smaller “domestic” retreat (Canada, US, and Mexico) a year and a bigger, more complex “international” retreat. We want to allow for plus 1s for the bigger retreats moving forward and keep the smaller retreats to team-only. Allowing plus 1s was such a neat aspect, but in order to maintain a balance of work and play, we want to make sure we have one retreat a year where it’s only the team traveling together.
On to the Next One
I can’t believe planning has ALREADY begun for our upcoming retreat. Upon returning, I took a much needed few days off to recover from all the hustle and bustle. Turns out retreat planning doesn’t stop once the trip starts, so I took some time to let the dust settle before taking on the next one.
I’m pleased to announce that our next retreat will be in October 2019, in Cancun! I have already started getting logistics together and initial planning has begun for the scouting trip which will occur early August. We’re currently narrowing down a list of resorts and will start getting the details nailed down in the next few months.
The Lima trip was an undertaking, but overall such a fun experience—I learned so much. I’m so excited for the future of our retreats, to implement what I learned, and document the process along the way. If you are on a distributed team and have experience with planning company retreats, I would absolutely love to hear from you!
If you enjoyed this article, please hit the green 👏 button.