Organizing team offsites.

management (208)

Last week, the team I support had our quarterly offsite. I’ve been running team offsites more and more frequently over the past few years, and have finally been able to nail down an approach that consistently feels like an essential, effective use of time.

My rules for effective offsites are:

  • Start with trust and safety. A good offsite starts with a group of folks who trust each other and feel safe bringing literal and intellectual honesty into the room. If you’re not bringing that team into the room, an offsite is a great way to start building it, but it does mean that you will probably not get to much else. I’m not particularly fond of the journey lines exercise, but it does a good job of something important: ungelled teams must learn to bring more of themselves into the room, not just their identity as “leader of some team”, which is a brittle identity likely to resist change and reflection. If your team hasn’t already gelled and built this sort of trust, then getting more of their identity into the room is the necessary place to start. A related, frustrating truth is that when you change the member of a team, you lose part of the built up trust and have to rebuild it.
  • What is the discussion that only we can have in this moment? This is an idea that I learned in amb’s Emergent Strategy, and encourages us to think about the structure of the day as a secondary concern, intended to facilitate the day’s reflection and learning. If the conversation is heading in a good direction then keep going with it, even if it means you won’t get to other planned elements of the day. Conversely, if a session isn’t leading to learning, then rework it or move on. This particular group of folks will rarely get the opportunity to grow together, don’t waste it on protocol.
  • You learn through reflection. Many teams get so busy that they try to outwork challenges rather than adapt to them, which leads to burnout. Use offsites to create a space for reflection, which is where the learning happens. Just as an offsite is a pause for reflection in your quarter or year, you can create reflection sections within your offsite itself. Give folks ten to thirty minutes to reflect in isolation and then coming back to share and discuss together (for smaller teams) or in groups of five to six (if the offsite is over ten folks).
  • Have a few key points and repeat them frequently. Folks can only remember so many things from spending a day together, so you really have to focus your day and your message. This most recent offsite focused on what we’ll need to do to support the continued growth of our business, products, organization and underlying infrastructure over the next three years’ growth.
  • Get other voices into the room. Get folks from outside of the team into the room to share their perspective. Teams are always at their best when they have someone else they want to impress just a little bit, and the outside perspective will help break the subtle equilibrium that a team develops as it works together. The “fireside chat” format is quite good for this, and I’ve also had success in inviting folks to attend the whole day, especially folks from different functions that partner closely with the team.

That’s pretty much it. Follow those rules and I think you’ll have a rewarding offsite no matter whatever else you do, and the format becomes less essential. If you are looking for a format, my typical offsite structure is along the lines of:

  • Breakfast & arrival (1 hour)
  • Check in and themes (0.5 hours but always takes 1 hour) – each person shares where they are personally and something they’d like to get out of the day.
  • Reflection exercise (1 hour) – an exercise that inspires reflection. This could be a “start/stop/continue” exercise, asking folks to consider how their current approach will scale for the next year, etc. The most important output is learning, not some kind of deliverable.
  • Work exercise (1 hour) – an exercise that creates an output, for example working on your team visions.
  • Lunch (1 hour)
  • Change the membership of room, typically by expanding group to include more folks. Perhaps bringing in tech leads, full management team, peers or what not.
  • Themes redux (15 minutes) – repeat the themes that you started the day with for the expanded group.
  • Reflection exercise (1 hour) – do another reflection exercise.
  • Work exercise (1 hour) – do another work exercise.
  • Fireside chat (1 hour) – bring in a user or peer and interview them, focusing on leaning into the day’s themes when possible.
  • Closing (15 minutes but takes 30) – recap the day’s themes and reference some things you learned over the course of the day.
  • Dinner (2 hours) – have a dinner somewhere else.

Remember, you’re there to have the conversation that only that group can have, so it’s fine to miss some of the exercises (this is why reflection exercises are always before the work exercises, it’s much better to miss the work exercises).

If you’re not doing quarterly offsites, give this format a try, and I think you’ll be pretty happy with it. It doesn’t require too much planning to go well, and your team will learn faster, gel more and be more rewarding to support.