Holding It Together as a Remote Company: Lessons from Our 3rd Retreat.
The first time I met my business partner, Jonathan Williamson face-to-face was 2 years into working together.
Which is pretty illustrative of our whole company culture; with a global crew that collaborates from Prague, middle of Kansas and even checking in via mid-flight at 30,000 feet, it’s hard to believe that establishing Cg Cookie as a remote company wasn’t part of our initial plan. Rather, it’s something that happened to us in the years since our humble beginnings in 2008.
Today, 4 employees, 12 contractors and thousands of users later, I like to think that I can offer some insight on how to hold it together the complex living organism that makes up a remote working culture.
Key word: company retreats.
Why do a company retreat?
No matter how hard you try to communicate with your team through persistent chat, weekly updates, or video conferencing, something just tends to get lost; the “why” tends to get chipped away at.
Retreats are like refueling stations before you head back out on a long road. You top off, check the map, grab a box of Lemonheads and are pumped to get moving.
One could argue: If the team were together each day, we’d experience this progress more often. However, to build on my amazing refueling metaphor, I feel we as a company would just hang out at the gas station wandering off form time to time, but always returning to comfort.
We’d fall into the slump of saying, “Morning Bob”, putting our headphones on and communicating through Slack in the same room!
A symptom of being remote is that we crave to see humans. So given the opportunity to spend a week with the ones you work with on a daily basis becomes incredible valuable. More importantly, you’re motivated to not waste time.
Just put it on the calendar!
One of the leading deterrents from planning a company retreat is thinking about planning it.
It’s difficult to justify, especially if business is crazy, which is the norm. You need to stop what you’re doing, find a location, plan flights, clear schedules with the crew and make sure you’ve got the budget for it.
So pick a date — and get the planning started. The results you will gain as a company, as a crew and a culture will outweigh any pain to make the retreat happen in the first place.
Buffer Travel Arrangements
Historically, on each of our company retreats a crew member’s travel is inhibited in some way. Whether due to tornadoes across the midwest, record snow falls on the east coast, or a rare 12-hour train delay. We’ve experienced all of them.
I’ve learned to buffer in at least 24 - 36 hours of travel time before and after.
Seems like a no-brainer, but for the first two retreats I didn’t do this. All will be well and flights will arrive, I figured. This resulted in a couple members showing up a day or so into the retreat.
Plan, but don’t over plan
Avoid scheduling 8 hours of slide presentations day in and day out. Additionally, don’t plan to spend all your time pissing the night away. There is a happy medium here: find it.
Retreat planning tends to go against the grain of project management ethos. You don’t need to account for everyone’s time and you certainly shouldn’t try to create metrics to measure its success there-after.
At CG Cookie’s first company retreat, we had zero planned talks. The second retreat, we sprinkled in a couple. For this third retreat, I feel we may have found the sweet spot.
Mornings are for talks, afternoons are for walks
Instead of saying, “Okay, at 9:30am we are going to meet and discuss Churn”. I’d recommend trying to setup 2–3 topics you’d like to talk on for the morning.
Keep your afternoons fairly open, and light. On paper this may look like, “OMG we’ve got nothing to talk about”. I’ve found the contrary to happen.
For the last retreat, we’d go from 8am — midnight almost each day, chatting, engaging on company discussions, and just enjoying each others company.
A retreat day schedule may look like:
Monday
- Breakfast: Local yummy restaurant
- Talk: Company retreat kick off — by Wes
- Talk: What the hell is Churn? — by Jonathan
- Lunch: In studio, grab from the kitchen
- Afternoon: Open
- Dinner: Order out, cook, relax.
The last day of the retreat I had nothing on the schedule. Nothing at all. As you could imagine, we were not short on things to do.
Make Food Accessible
Not everyone eats on the same schedule or will have the same affinity for foods you may like. It was less stressful to have access to food on demand.
Stock up!
We did have a couple planned dinners, simply to get the crew out and away from our computers. During this particular retreat the crew took on trying Oysters for the first time!
Go Snowboarding!
Though this idea seemed like a bad one once I had buckled myself onto the damn board, it was a blast and something I’ll never forget.
Avoid searching for corporate team building events. Events where everyone is stuck in a room, writing on note cards, or doing the paper plate exercise.
If you’re able get the team outside, involved in the community or quick game of frisbee golf, do it.
The goal here is simply to get to know each other. This pays in dividends when interpreting tone on chat messages for example. If you know the person, it is much easier to translate tone correctly, than if you’ve never met them in real life.
Play games!
With a Settlers of Catan battle taking hold of our final night (and talks of a traveling trophy for next year), our retreat has given rise to new company rituals.
In the end..
We are a relatively small team of 6–10 people that gets together, so we don’t have to work on the scale of 25–50+ remote employees.
In each scenario the fundamentals should be the same; have fun, talk with other humans and fill up for the long road ahead!
Things we are looking to try the next time around
- Offer a consumable project that entire team contributes to over the timeframe of the retreat.
- Getting on a two retreats a year schedule. Once is just not enough.
- Go somewhere warm. The last 3 retreats have involved snow, and temperatures around 20F.
