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Ten tips for planning an awesome company retreat

Oct 23 '15

Third & Grove is a distributed company. Half of our team works in physical offices in Barcelona, San Francisco, and Boston, and the other half work remotely from all over the United States in places like Ohio, New Hampshire, and Wisconsin. We seem to have a lot folks who like the cold.

Some of our team members had never met their colleagues, even though they have been working together for years. So we decided to throw our first annual retreat to bring everyone together for two days of bonding, fun, and planning.

Tip 1: Research, Research, Research

The first thing I did was read up as much as I could about other companies and their retreats. Either most digital agencies don't do retreats or they don't share anything about them. Part of the reason I'm writing this post is to hopefully help others planning similar events. Luckily, our good friends at Social Driver shared information on their retreat and their recap got my creative juices flowing.

Tip 2: Pick an easy location

A benefit of being a distributed company is we could have our retreat anywhere. Tony and I decided fall was our window in terms of schedule. We also have the best office in Boston and lots of space there, so it was a natural pick for our first location. I was also planning this retreat and it was my first time, so leveraging everything I know about the city I live in made things easier to plan.

We aren't sure about next year's location but have toyed with the idea of picking a new city each year. We may also go to San Francisco. Sorry, nothing official yet for retreat 2016.

Tip 3:Identify your goal

Tony and I had a very clear goal for doing this retreat: Bring the company together to bond and share our vision of where Third & Grove is headed. Once we were crystal clear on the goal it became much easier to plan things.

Tip 4: Have some fun

We decided early on that we would spend the mornings doing company meetings focused on our vision, values, process, and approach, and spend the afternoons and evenings having fun together. This schedule balance worked out very well.

Tip 5: Be flexible

I decided last minute on Friday to change our lunch plans. Instead of hitting a yummy dumpling restaurant, we headed into the city and took advantage of the great weather to hit the food trucks in Dewey Square and eat together on the grass in super comfy adirondack chairs. This turned out to a great hour of relaxing and bonding in the warm New England fall sun.

Lunch in the New England fall sun in Dewey Square
Lunch in the New England fall sun in Dewey Square, downtown Boston

Tip 6: Give back

One of the most popular events was our charity contest on Friday. The Friends of Boston's Homeless is a great organization that helps those in danger of becoming homeless or those on the streets get back into homes. One of their needs is move-in gift baskets for people moving from the street back into a home.

We split every one up into several teams and I gave each team a hundred dollars cash. The goal was to creatively stretch this money as far as possible using anything in the city. We immediately started the clock for two hours and sent everyone out into the city. Tony and I picked a winning team and gave them a special prize at our team dinner Friday night.

tag retreat winning team
The winning team!

Tip 7: Do lightening talks the first day

We made every person on the team do a 3-5 minute lightening talk on something they were passionate about unrelated to work. We did this on day two of the retreat but in retrospect day one would have been better. Discovering all the awesome passions of the team – from making music with classic 90s Gameboys that is popular in Brazil to making miniature models entirely out of paper to master bread baking skills– led to some fun conversations. Would have been good to know those on day one.

tag retreat musical gameboy
Yes, that is a classic 90s Gameboy turned into a musical instrument

Tip 8: Build something

We spend our days building software together. For the retreat I thought it would be fun engineering something physical together. We headed to Artisan's Asylum, a maker space down the street from our office. We broke into teams of two and I tasked each team with building a body part that we would assemble into our new robot mascot: Tagbot.

tag retreat brian and pavel made TAGBOT'S armored leg

Brian and Pavel work on Tagbot's legs
Tagbot’s hands being designed
Tagbot’s hands being designed
Tagbot lives!

Tip 9: Ask how it went

When the retreat was over we sent an anonymous survey to the team to find out what worked well, what didn't, and what we can do different next year. The results will help us make this event even more impactful next year.

Tip 10: Distribute the schedule

While I shared the schedule in the opening address of the retreat in a slide during a presentation, I didn't distribute an electronic copy to the team. This would have been very helpful to folks to know where to go.

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