Back in simpler times, before sourdough starter became a rare asset and before we knew anything about the underbelly of exotic animal parks, we used to work almost entirely in offices. And on occasion, leadership teams would have a “strategic off-site” away from the office (as the name would suggest.)
Historically, off-sites were viewed as an opportunity to get away from the day-to-day distractions, to think strategically, and to come up with long-term plans. If you want to go down a YouTube rabbit hole, check out the videos from the Next Computers offsite led by Steve Jobs. Occasionally off-sites were called to deal with a specific crisis, and other times they were just boondoggles.
As COVID-19 cases come down, and vaccination rates creep up, executive teams around the world are starting to plan their first in-person gatherings and many are kicking things off with a strategic off-site.
Given that many companies have given up their offices, and those that have kept them are frequently returning with a more flexible “hybrid” structure where people can either work from the office or remotely, off-sites are taking on a new and greater significance.
Having been through a few of these myself and having talked to hundreds of WorkPatterns customers, we thought we’d share some off-site tips and techniques.
As with any important meeting, preparation has a massive impact on the effectiveness of off-sites. At the bare minimum, the leader of the off-site (CEO or department head) should circulate an agenda at least 2 weeks ahead of time. Not only does that help to set expectations and ensure all the team members are prepared, but it also helps to crystalize the off-site’s goals and ensure there’s a clear focus.
At the top of the agenda should usually be a presentation by the off-site leader. This will set the tone and focus for everything else. I’ve found it to be especially useful to set some high-level themes or a clear objective that can put conversations into context.
As a simple example, at our recent mid-year offsite, I set a high-level company objective to double our customer base in the next 5 months. With that clarity, we could decide if something was worth spending time on by asking the simple question, “Will this help us double our customer base in the next 5 months?” If not, we should put it in the backlog for now.
The final piece of stage-setting involves grounding the team in reality. I’ve found it’s best to quickly move from a high-level objective into a metrics review. This helps to root everyone in reality. People tend to come into off-sites with their own set of beliefs or interpretations about how the business operates, so it’s helpful to get everyone working from the same set of facts. I recommend being as transparent as possible, so people can have an informed discussion.
After setting the stage, it’s usually useful to have a session that allows people to get a bunch of ideas out. In addition to generating ideas based on the themes and the data from the first session, chances are, your team came with preconceived notions of things they want to bring up and pet projects they want to promote. Before having detailed debates and developing specific plans, it’s often helpful to get all of that out. Here are a few frameworks that are helpful to go broad:
Now that you have a bunch of ideas, you’ll have to get a sense of which to focus on. I highly recommend setting expectations that the output of this exercise is not a final decision, but will be used as a data point for the appropriate stakeholder to decide on priorities. The value of prioritization exercises should really be in the discussion and alignment around what a certain idea means and how it could be scoped. For example, the idea to “improve onboarding” might be a popular idea. Well, what does that include? Does it mean a mobile app? Does it mean demos? Prioritization exercises often help to flush out the details and result in ideas getting more specific.
A few useful frameworks for prioritization include:
Hopefully, you’ve been recording action items along the way, and now is the time to raise any follow-ups that haven’t already been captured. We obviously use our own product for this since WorkPatterns does a great job of handling action items and goals but whatever you use, it’s critical that there’s clear accountability coming out of an off-site.
It’s usually helpful to schedule a follow-up for people to present on action items that came from the off-site. This usually includes things like roadmaps, project plans, and other department-level plans like Marketing, Sales, and Engineering.
The future of remote vs in-person work is still murky, but it does seem clear that there will be some increase in hybrid and flexible work arrangements for the foreseeable future. That makes off-sites an increasingly important tool in operating any business. The first time people see each other in over a year will certainly come with unprecedented energy and excitement, so putting a little prep work upfront is worth the effort.