Work + Vacation = Workcation

Published on January 12, 2013 on The Lean HR


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Twice a year at Sincerely, we take the entire team on a workcation. A workcation is a combination of work and vacation with your coworkers at a location where everyone can work together in an environment where they can relax, get work done, and get to know each other a bit better.

We make these trips because we feel they are important bonding opportunities, provide a great environment with limited life distractions, and allow us to focus on building Sincerely into a great company that creates great products. We also believe that they align with our core values of Curiosity & Health. We travel to new places to learn new things, and to learn from each other. We also spend a good chunk of time exercising and clearing the mind to refresh the soul.

We were fortunate to begin 2013 in Maui, with the entire team, paid for by Hyundai.

How does it work? Gussy it up however you want, Trebek. What matters is does it work? - Sean Connery (SNL)

Workcations work when the entire team is as productive or more productive than a normal day in the office. It allows the company to justify the expense and continue to keep making these trips in the future. Before leaving on a workcation, the team outlines objectives and projects that need to be worked on. We also have a pretty good idea of the activities outside of work that will be available and who is interested in taking advantage of them. We provide a framework for the team on what the company is “covering” and what individuals are responsible for. In our case, we cover the flights, rental cars, lodging, stocking the house with food, lunch, and a few team dinners. Activities such as snorkeling or a massage on the beach is up to the individual to cover.

Preparation “Failure to prepare is preparing to fail.“ - John Wooden

The team should come with goals that they want to accomplish. For an engineer, it could be a complete set of features. For a designer, it could be a new set of wireframes or in our case, Valentine’s Day Greeting Cards.

The team should also come with activities they want to do outside of work such as snorkeling, whale watching, or seeing the sunrise at Haleakala. It’s easier to coordinate these trips in smaller groups so finding out who is interested in what earlier allows ample time to book a tour to make sure there is availability. We also bring other fun activities for people to participate in while at the house. We usually bring a few board games (Settlers, Blockus, Deck of Cards, etc.) as well as fun equipment for swimming, running, and reading.

The team should also think about breakout sessions either for team building, brainstorming, or discussing features on the road map. I believe these sessions are some of the best moments of a workcation. We usually run sessions in small teams throughout the day and a session with the entire team in the evenings a little bit after dinner.

Finally, you should have a good idea of what accommodations you will have, if people are comfortable sharing beds, and sleeping on the floor. Luckily in Maui, sleeping outside is a luxury people volunteered for. I would also recommend making a list of equipment that you will need (power cables, chargers, power strips, projector, any equipment you need to do your work, and office supplies such as post-its, markers, pads of paper).

Get Sponsored “I scratch your back, you scratch my back.”

We had the majority of our workcation sponsored by Hyundai. Though we are a consumer facing company, we built a product for businesses called Postagram Engage. Essentially we operate as a mobile photo team that takes pictures of guests at events and sends those pictures on branded postcards to their doorsteps. We were brought out to Maui to work at Hyundai’s Tournament of Champions, the first event of the PGA Tour in 2013.

We took this opportunity to bring out the entire team where the photo team worked at the Golf Course and the engineering and design team worked at the house on their projects. We were able to make it work financially by substituting hotel rooms for a large house, minimizing eating out and focusing on cooking at the house, and finding cheaper flights leaving from San Jose and not SFO.

Out of the 8 days we spent in Maui, 4 days were spent working at the Golf Course while the rest was spent at the house. I’m confident that the team is refreshed and we already have some great momentum heading into 2013.

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