In my last company, we had a distributed management team. 6 team members across 3 states. It took us a while to figure it out, but we eventually found a healthy cadence of huddles, team meetings, and everyone’s favorite: retreats.
Team retreats are awesome. We ended up scheduling quarterly management team retreats. Occasionally these would be schedule during the 2-3 days before a Board meeting, so we could prepare and strategize for the next quarter, then use the Board meeting as a presentation/finale for the output of the retreat. Most often, however, these retreats weren’t anchored by another event and we would just go find somewhere quiet to get several days of focus on the company. Here are some ideas and lessons learned about retreats for startups looking to do these.
Always Plan a Detailed Agenda in Advance
I’ve learned this lesson the hard way. Any retreat where you don’t have a detailed agenda will go sideways. People are traveling and having fun so often it is way too easy to throw structure and planned activities out the window. It’s critical to discuss the agenda 2-4 weeks before the retreat and have the entire time on the same page. If everyone has input to the agenda (at least the high level), it has a better chance of success. You also can play around with which team member plans the agenda. You might trade this off to share ownership of the schedule and planned activities among the team.
Balance The Work vs. Play Time
This is a best practice for EO retreats and it translates well to team retreats. As you plan the agenda, decide in advance what breakdown of work vs. play time you want to build into the retreat. Assume you have a 10 hour day to plan. Decide what percentage of time will fall into which categories. Generally, we found a 50/50 or 60/40 (work/play) was the most productive. You will find that being together away from the office yields the most productive work time you will find. It’s intense and exhausting. Trying to work all day without fun excursions isn’t fun and the productivity will tank fast.
We always liked to rent a house or a cabin and stay together. (Another lesson learned from EO.) Going back to hotel rooms at the end of the night is an energy killer. We all still had our own rooms and private/quiet space, but there’s a different vibe when you are sleeping under the same roof and are responsible for taking care of the facility as a team.
Format Idea: Single topic per day or Half day
One of the formats that worked well for us was to avoid dealing with the little “piddly-sh*t” that you deal with every day at the office and take LARGE chunks of time (3-4 hours) and focusing on a single deep dive subject. Whether it was a new product launch, a new market, or even a single big problem, like culture issues. We found these deep dives to be very healthy. Most entrepreneurs don’t have the attention span to imagine spending 4 hours talking about a single subject, but some topics are important enough to justify this intense focus… like culture.
Format Idea: Innovation Retreat
A few times over the years, we planned these “innovation retreats.” On these retreats, we intentionally agreed to not discuss current problems and fires and only think ahead. Blue sky sessions. Product brainstorming. How to better serve clients or help them accomplish their mission. We usually came away with 2-3 big ideas to monitor and 1 big idea to actually tackle over the coming quarter. It was powerful and energizing to pull our head out of the grind and find something that is visible forward motion.
Format Idea: Pre-Planned Exercises Like Start, Stop, Continue
One exercise we did that worked well was to have each team member write down and bring 3 lists to the retreat. A list of things the company should START doing, a list we should STOP doing, and a list of things we should CONTINUE doing. Each team member presented their list and they were discussed. Tons of action items came from these meetings any time we did them.
Format Idea: Core Values Only
In the early days of our company, we realized that we didn’t have a clean set of written core values or a clear understanding of our WHY. One of the most painfully frustrating, yet equally rewarding retreats was the one where we agreed to discuss nothing the entire time but our core values. Given how important these are to your culture and ultimately determine your success, I don’t think this is a bad idea. Really taking time to debate and process core values was useful for us.
Team retreats are awesome, and I could write 100 more posts about these. In the early days of a startup, obviously you can take the whole company, but as you grow, this normally becomes financially impossible. Still, remember to have some all-hands events when and where you can.