Off-sites are the new on-sites

Adam Berke
July 7, 2021
4
Minutes

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.

The formula for planning a great off-site

1. Set the stage

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.


2. Go broad

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:

  • Brainstorm problem statements from the customer’s point of view. For WorkPatterns, these could be things like “It’s too time-consuming to prepare for 1:1s” or “It’s hard to give constructive feedback on a regular basis.” Once you have a bunch of problem statements, you can prioritize which are the ones that would be most impactful to solve. That tends to be easier than jumping right to specific features.


  • Use “How might we?” Once you have some good problem statements, you can use the phrase “How might we….” to start addressing the problem statements that bubble to the top of the list. Using the example above, we would say “How might we save people time preparing for their 1:1s?”


  • Allow for individual thought. Instead of having everyone brainstorm all together, there’s a lot of evidence to suggest that it’s better to brainstorm alone first, then share your ideas with the group. This helps to avoid the loudest voices having the greatest sway and ensures there’s a good breadth of ideas instead of just riffing on a few ideas that people seem to like.


  • Crazy 8s are a helpful tool for individual brainstorming. Fold a piece of paper in half 3 times. This should result in 8 boxes. Then set a time for 8 minutes and instruct the team to sketch an idea for a specific “how might we.” After each minute, move on to the next box. At the end, people can present their favorite 2–3 ideas depending on the size of the group.

Crazy 8s example

3. Narrow it down

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:

  • Impact vs Effort. This involves putting impact on a vertical axis and effort on a horizontal axis. So ideas in the top right quadrant are high impact but also high effort and the bottom left would be lower impact but also low effort.
Impact vs Effort Matrix


  • Stack ranking is a way to assign a value to different ideas by scoring them across different categories. Everyone in the group would give each idea a score from 1–4 (it’s useful to use even numbers so people can’t just use the middle point) across categories like “revenue impact,” “ease of implementation,” etc. You can even assign a multiplier to different categories that are especially important to weight the scores for that category.


  • $10 to spend is a framework that helps to make prioritization more tangible. Basically, everyone on the team gets a dollar amount to split up between investments in different ideas. Forcing people to put money on the line has a way of forcing clear priorities as a former pro poker player and decision-making expert Annie Duke discusses in her fantastic book Thinking in Bets.

4. Align on next steps

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.

Some other off-site suggestions

  1. Leave unstructured time. This will likely be the first time people will have seen each other in a long time, and possibly the first time many people will be meeting in person ever. Off-sites can be a great opportunity for people who usually only meet over Zoom to have in-person meetings.


  1. Have a follow-up on the calendar. Having a follow-up meeting already on the calendar is a useful way to avoid rabbit holes. For example, if the team is spending too much time on a specific topic, it’s useful to assign a specific owner to the topic and allow them to come back with solutions at the follow-up meeting instead of derailing the agenda by hashing out things in real-time.


  1. Create a parking lot. Speaking of rabbit holes, it’s useful to have a “parking lot” for the off-site where you can document topics that seem to be consistently derailing the conversation. Sometimes tricky topics need to be worked through then and there, but things that can’t be solved in real-time need to be captured. Those ideas should be added to the parking lot.


  1. Take care of logistics ahead of time. This one might seem obvious but, is often overlooked (especially as a startup). Do yourself a favor and, order lunch in advance at a scheduled time, make dinner reservations, nominate someone to bring office supplies you’ll need… if you want everyone to show up having eaten breakfast already, let them know! Chances are, many people are traveling from out of town and aren’t familiar with the area. You’ll be less stressed and your team will be more focused and energized if these things are taken care of already. 


Off-sites are a critical tool for modern workplaces

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.

Start having meetings that work together with WorkPatterns