Why we retreat

This is the first in a two-part series about our silverorange company retreats. It focuses on why we have a retreat, while the second part will focus on how it is organized.

We held our first annual silverorange company retreat three years after our founding, in the winter of 2002. We gathered in a basement of the Kindred Spirits Country Inn & Cottages, in Cavendish, Prince Edward Island. At the time, the inn was owned by the parents of our then-CEO. Now he owns the inn and we have a new CEO, but that’s another story.

Over those few days in 2002, we played video games (4-player Mario Kart on a GameCube, projected on a wall), ate, and planned our coming year as a company. None of us were married and none of us had kids. Now, fourteen years later, we have 18 kids between all of us (you know, respectively).

This month marked our 14th annual company retreat. Since that first winter, we have changed venue a few times, added a few extra days/nights to the schedule, and increased the budget. However, the basic purpose of the retreats hasn’t changed. It’s an opportunity to retreat from our regular routine, enjoy ourselves, and revisit what kind of company we want to be.

It’s not a vacation

While we do have a lot of fun at the retreats, most of our days are taken up with fairly intensive meetings. This year we improved the balance to keep from burning out. Still, our retreat isn’t a vacation. It’s a time for everyone to participate in shaping the direction and day-to-day working of the company.

When we only had one real meeting a year, it was a big one.

In the first few years of our retreats, we weren’t a well-run company. We shied-away from structure, authority, and even responsibility. We weren’t a mature company, nor were we particularly mature individuals. We survived because we were a small, tight-knit group, but I’m sure this lack of organization held us back.

Years into our company, this beautiful chaos started to become more chaotic and less beautiful. In response, we invented what we thought at the time was a bold and innovative solution. We called it the “board of directors”. While the day-to-day operations and management of the company remain fairly flat, this group of six people in the company met monthly to review and direct the state of the company. In hindsight, we’re alarmed at how we managed to fare at all without this level of oversight.

Before we had this board of directors our annual retreats were a frenzy of planning. We were packing an entire year of management, financial oversight, client and process review, all into a few days. It was exhilarating, but it was also ridiculous.

Even a well-run company can stand to retreat now and then

Now that we’ve matured as a company (and hopefully as individuals), we have more structure in place. We aren’t surprised at the end of the year by how much money we made (or lost). We have regular oversight of financial, management, and other business issues. It’s far from perfect, but it’s much better.

With better machinery for managing the company throughout the year, we no longer have to fill our retreat days with the basics of figuring out where our money came from and where it went. We have more freedom to think about bigger issues. We can look further ahead with more accuracy. We can work through what kind of company we are, and what kind of company we’d like to become.

There are several goals for the retreats. First, we reflect on the year that was. We celebrate our achievements and reflect on our failures. A secondary, but perhaps equally important goal is to spend time together as a team in one place, outside of our regular work environment. We prepare and enjoy meals together. We play games. We catch up with the remote employees.

We try to leave our retreat with an appreciation for, and understanding of, the previous year. We leave with a list of specific and general goals, but perhaps more importantly, we aim to leave with a shared understanding of the direction we’re all pushing in.

It’s still worth it

This year we asked each employee (one-on-one) if the company retreat was still worthwhile. The answer was unanimous and enthusiastic (and it was ‘yes’). I leave the retreat feeling great about the year that was, the year to come, and most importantly, about my friends and co-workers at silverorange.

Now, I’m off to unpack my snow pants and bathing suit.