How We Plan Bi-Annual Team Retreats for 30+ Teammates at ConvertKit
At ConvertKit we take two week-long retreats per year. One in the winter and one in the summer. This February 2018 will be our 4th retreat and we can’t wait to get together again. Nicole did a great job of explaining why we take retreats here.
It’s incredibly important for our 100% remote team to connect in person, align our strategy and values, and accumulate enough hilarious (to us) inside jokes to last for six more months.
So now that you understand the “why” for our retreats, I would love to share with you the “how”.
The process we use to plan for our team retreats
I’m an executive assistant at ConvertKit and I started in July of 2017, about a month prior to our summer retreat. Part of my job description was taking the lead on planning our retreats. I work very closely with Ashley, our Director of Operations, and Nathan, our Founder/CEO, on planning every detail to make sure we get the most out of these experiences as a company.
When I started, they had planned the basics for the upcoming retreat, but there were still lots of details to work on. They had already selected the location (McCall, Idaho), rented two amazing houses for us, and people had mostly booked their travel. We still needed to plan activities, the schedule, food, room assignments, and more.
So together we finalized all those details in just a few weeks and ended up having an awesome retreat, but not without quite a bit of scrambling! Our marketing designer, Charli, put together this great recap of that retreat if you’d like to see:
Here’s how we make our retreats happen
This time around we are getting a bit more of a head start and trying to extend our planning timeline. In fact, we’re already working on our summer retreat for next year!
Here’s how we do it.
Date
We already have our timeframe in mind for each retreat. We shoot for late January/early February in the winter and sometime in the month of August in the summer. We check for any major conflicts during those times and we do our best to work around whatever we can.
Our goal is to get the dates announced as early as possible so that people can plan their personal commitments around the retreat and we can get 100% attendance. We arrive on Sunday evening and depart on Friday morning, giving us four full days to work and play together.
Location
Next we tackle location. This is definitely the hardest part, and takes the most time. The bigger we get as a company, the harder it is to find everything we want in a location, within our budget.
We prefer to rent one large house if possible, and we particularly look for a place with a huge open living space for team meetings and work time. We have used tools like AirBnb, reached out to property management firms, and just googled our hearts out to find the best places.
We happen to have quite a few people in Idaho so we’ve centered our summer retreats there, saving us money in rental cars and flights. For winter retreats we like to go somewhere warm! This coming February we landed on Oceanside, CA and we are so pumped to be right on the ocean with some (hopefully) sunny days!
Once we’ve found a few locations that could work, we check availability and negotiate pricing. It helps to be somewhat flexible on your dates at this point, but once we find one that lines up in our budget and timeframe we book it!
Next step is telling the team, which is always really fun. We share the final dates and the location with everyone and the excitement really starts to build!
Transportation
We have everyone book their own airfare to and from the retreat on their company credit cards. Since we are a remote company, people have the option of flying in early or leaving later and working from whatever city we have picked. We book a smaller rental house for our international employees who need to come in early to acclimate to the time zone and book as many rental cars as we need to carry the whole crew.
Food
We are really lucky that Nathan’s wife, Hilary, loves to cook and has the talent to feed all 30 of us effectively. She has cooked at three of our retreats, but this February she has a prior commitment and told us she can’t make it.
After we got over our sadness, we did what anyone does when looking for food options — we went on Yelp. I asked the top five private chefs in the Oceanside area for bids and we narrowed it down based on price and menu options.
We have a couple of people with food allergies and preferences so it is very important to find someone who understands that and is enthusiastic about making sure everyone is well fed and taken care of.
Activities
At each retreat we schedule two half-day activities to give us time to kick back and enjoy being together in person. We do some initial research on what is available in the area and then we ask our team which activities they are most interested in.
We usually post in Slack or Basecamp and have people vote on their favorites. The goal for each activity day is to have one Action/Adventure option and one Rest/Relaxation option. Once we know everyone’s favorites, we see what will fit within our schedule and budget and book those.
We’ve done things like surfing, paintball, white water rafting, massages and escape rooms. It’s always one of the most memorable parts of the retreat and a lot of fun. It’s amazing what you can learn about someone as they’re trying not to get shot with a paintball!
Survey
About this time in the planning process we like to send out a survey to our whole team. This is where we get detailed information that helps us plan the best retreat for each person. We ask things like:
- which specific activities they want to sign up for on each day
- what their rooming preference is
- what food allergies and preferences they have
- what essential snacks we should have on hand
Most importantly we ask everyone what they want to get out of the retreat, and we try to structure the schedule around those things.
Room assignments
Because we favor houses over hotels, we usually can’t give everyone their own room. Sleep is an important part of productivity and overall mood, so we spend a good deal of time trying to nail down the best configuration for people based on their room requests.
Our goal is to have no more than two people per room and to have early bird rooms and night owl rooms. It doesn’t always work perfectly, but everyone is flexible and accommodating and we do our best with the rooms that we have.
Schedule
At this point we have the activities and meals scheduled, so we fill in the rest of the time with group work, team meetings, and all-company strategy sessions. We’ve learned over time that unstructured work time is really important to build into the schedule and this is when some of the best connecting and problem solving happens. We also block out time for unsolicited feedback within teams and between teams. Our directors determine the topics of the group sessions and any other meetings that need time.
Once that’s all settled, I create a schedule document that includes all meetings, activities, and meals. I also create a Google calendar with all events on it so people can see it anytime on their phones.
Extras
We love to surprise and delight our team with things like:
- hand-picked gifts for each person
- charity events where each person gets to give money a non-profit they love
- team awards with awesome prizes like capes and walkie talkies
- profit sharing checks with hand written thank you notes from the leadership team
Each retreat we do something different or put a spin on something we’ve done before. This is one of the most fun parts of planning! I’d highly encourage anyone planning a retreat to add in a surprise of some kind and change it up each time, it really makes each retreat so special.
Reading through all this it might sound like a lot of work, but it’s honestly one of the most fun parts of my job! Ashley says her favorite part of retreat planning is “planning surprises and creating opportunities for the team to connect whether it’s casual conversations over meals or in depth ones on important topics.”
And Nathan likes planning the activities the best. “Especially for the McCall retreats where I get to take the team to some of my favorite places (like boating on Payette lake) from growing up.”
For me, I like all of it. I love seeing the pieces fall into place, slowly at first and then in a rush toward the end, knowing they will all lead to this amazing experience for me and my coworkers.
It’s one of the ways I feel like I contribute the most and that is extremely satisfying.
If you’re planning to start hosting team retreats for your company, I hope this guide has been helpful. And if you have any questions, comment throughout the article or send us an email to help@convertkit.com — we’re happy to answer them!
