Structuring a Staff Offsite

Guesswork Unveiled, Issue #16

Structuring a Staff Offsite

Guesswork Unveiled, Issue #16

I’m a few weeks removed from our first-ever full-team staff offsite — it was a truly meaningful event for me, the team, and our business overall.

I certainly don’t have the experience to espouse best practices on the topic, given this was literally my first one. However, I thought I would share how we structured it from an agenda & topics perspective, as well as some thoughts on what worked well for us.

I asked a TON of folks for advice through the offsite prep process, so credit really goes to my support network. (Hat tip to Rory Tyer for doing two coaching sessions solely focused on preparation for the offsite.)

Let’s dive in!

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Prep Work

We set aside meaningful time to talk through a game plan and prep for the offsite.

Goals

First, I would start by defining goals for the offsite — why is it worth the cost & work disruption to do this? For me, I defined them as:

1. We explain the new concepts of our company mission, vision, and mindset in a thorough, understandable way to the whole team.

2. The leadership team leaves the retreat bought in and ready to keep reinforcing those concepts to the full team.

3. The whole team leaves more excited to be on the team than when we started.

Group Structure

Second, I would then think about the various stakeholder groups coming to your offsite. Are there natural groupings? Are there different functional areas you want to connect together more? You can adjust the cadence of your overall offsite accordingly.

In our case, we had ~20 total people attending, of which ~6 were in the leadership team. So we had that leadership team come out on Thursday night. We did one session Thursday evening, and a second session Friday morning. Then the rest of the team joined on Friday around mid-morning so that the rest of the day was spent in full-team programming.

Agenda Building

Third, spend time building out the actual agenda required to support your goals. We broke them each segment into one to two-hour chunks. We assigned who would be the primary facilitator for each section as well — in our case, I was the primary facilitator for all segments except one. More on agenda building below when I share our high-level offsite agenda and a detailed working session agenda.