Reflections on a Successful Company Offsite

Earlybird
The Earlyblog
Published in
4 min readNov 26, 2017

Earlybird hosted our third annual company offsite this month in Milwaukee. Here are some thoughts on the experience from product designer Brad Siefert.

Brad Siefert (author, right) with developer Kris Kroski during the morning session of our company offsite

It can be so easy for a company to lose track of time. The beginning of a new year or quarter comes full of excitement, with a commitment to new ideas and methods, only to be quickly caught up in the day in and day out rhythm of work. Technology companies, especially ones that do project-based client work, sometimes fail to be reflective, which is why at Earlybird we have an annual tradition of conducting a company offsite event. The idea is to shut everything down for one day and go somewhere different, reflecting as a team on where the company is and where it’s going.

Startups are not always known for this sort of self-examination. The quick-paced environment and constant focus on growth does not leave a lot of time to look out the window and ponder one’s existence, but we have found that these retreats are an incredibly effective way for everyone to recharge, and for the company as a collective to be reminded of our values.

For us, one of these values is, “Engage in lifelong learning,” and in years past, many of us had commented on how well we’d done in owning that value. This year, when re-asked the question, it was inspiring for me to realize that I hadn’t learned as much in 2017 as I had hoped. However, if I hadn’t been prompted to consider it, I don’t think I would have recognized this.

Another one of our values that we always have a good discussion around is our goal to “leave everyone in a better place than we found them.” This value is deeply convicting because I think it requires a steadfast commitment to our clients, even in the moments when we might disagree. This goal also applies to the employees of the company as well, and it was a good exercise to think about how we could leave each team member, current and former, in a better place than when they first encountered Earlybird.

The Hive Offices, where we hosted our afternoon session on strategy and company finances

We’ve found that the location of an offsite is very important. We’re lucky to be based in such a great city, Chicago, and the first year we decided to leverage our contacts and borrow conference rooms at other local startups, which worked really well. The past two years, though, we’ve had way more fun getting out of the city and going to nature preserves, local breweries, and other attractions. In the fall of 2016, we spent our time in West Michigan, mostly around Sawyer, a small town that boasts some great restaurants. We hiked around the Michigan Dunes and went on a really nice distillery tour.

This year, we drove a little further to Milwaukee, Wisconsin, and enjoyed a few of the great coffee shops and breweries that city has to offer (including Bella Caffe, Milwaukee Ale House, and Lakefront Brewery), as well as an afternoon strategy session at The Hive Offices coworking space. Even the drive back and forth is a fun part of the day: while one car had deep conversations on a variety of subjects, the other had a near-deafening, guilty pleasure 90s sing-a-long on the way home.

The costs of organizing an event like this can be really reasonable and are easily offset by the gains in morale and the investment in our employees. Two of our colleagues work remotely, and having them back for this time was a big highlight for us all. We’ve found that an offsite like this creates a sense of buy-in, excitement, and teamwork for the upcoming year. We’re hoping to expand into hosting them more frequently so that we can constantly have a sense of purpose for the work we do and continuously keep driving home our values.

Brad Siefert has been a designer at Earlybird since early 2013 and is instrumental on a wide range of projects ranging from native mobile apps to custom analytics dashboards, web marketplaces, and more. You can follow him on Twitter or check out some of his visual work on Dribbble.

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Earlybird
The Earlyblog

Chicago-based developer of custom cloud and mobile software, emphasizing solutions for smarter business operations. Learn more at earlybird.co.