Johnson Cook

Atlanta tech investor. Entrepreneur.

Johnson Cook - Atlanta tech investor. Entrepreneur.

Team Retreats


Team Retreats _ CabinIn 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.

Stay Together
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.



Category: Ideas
  • BarrettBrooks says:

    Really enjoyed this post, Johnson. I’ve also found team retreats to be an incredibly effective way to carry the momentum forward with a team or organization. Your tips for dividing between work and play, staying under the same roof, setting the agenda in advance, and having deep dive discussions are spot on.

    I’d add to this discussion that giving everyone a role to play during the retreat is a great way to foster confidence and team building. Especially as organizations grow, it can be difficult to create an environment where everyone feels valued and heard enough to share their most daring and innovative ideas.

    Thanks for this post — keep ‘em coming.

    September 6, 2013 at 3:41 pm
  • Dave says:

    Great post, JC. Brings me back a ways. I still refer to our innovation retreat in the mtns. I agree that staying under the same roof is important. And switching up locations is important. Love Barrett’s idea of taking on roles.

    There are a lot of tools you can use to address the dynamics of your group. We used “red cards” to basically stop a conversation when it’s gets too heated or is heading in the wrong direction. Anyone can hold up the card and the conversation stops until a later time.

    Of course a parking lot is very important to stay on topic.

    This time around (which coincidentally was last week when you wrote this) we each came up with 1 topic and sent out a report and associated articles and videos on the topic so we could be prepared coming into the retreat. It was extremely effective and focused our discussions into 4 equal parts.

    Good post.


    September 8, 2013 at 8:16 am
  • Jeff Hilimire says:

    Team retreats are terrific and it sounds like you know how to run these effectively which can be difficult with a group of leaders. To me the biggest issue – and I’ve been guilty of this in the past – is keeping the momentum going post-retreat and having actionable follow up tasks and goals.

    September 10, 2013 at 6:57 am
    • Johnson Cook says:

      Big point! Sometimes we nailed this and sometimes we bombed. Our best cadence was a weekly call with the exact same team to only discuss the action items from the retreat. The biggest lesson learned is to set attainable and realistic goals. When we did that right, everyone looked forward to the weekly calls because it was fun to report on progress. When the goals were too lofty, the weekly calls were a depressin burden and reminder of the heavy liftin yet to be done.

      September 10, 2013 at 7:10 am

Your email address will not be published. Required fields are marked *