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Seven tips for a transformative offsite

It's that time of year again. 2024 is already peaking its head around the corner, and if you haven't already started planning for it, you know time is running short. And in

a world of distributed and remote workforces, doing the planning work in person, at an offsite, has never been more valuable.

Done well, offsites are more than just extended planning meetings; they are pivotal inflection points that realign your team and define the trajectory of your organization for the year ahead. We've run hundreds of them and want to share a few simple tips that will help you have an offsite that leaves your team re-energized, focused, and connected.

  1. Plan at least four to six weeks ahead. The most effective offsites are those where people feel heard and show up knowing what to expect. Planning well in advance enables time to gather input and ensure attendees and their teams can complete any preparation. Conversely, “winging it” rarely leads to clear outcomes and often negatively impacts confidence and camaraderie.

  2. Be hyper-focused on agenda design. Every minute of your time together is valuable, especially if you are not in the same office together day to day. A two-day, 12-person offsite is 192 hours of your most valuable team members’ time - and that’s just for the offsite itself! Try to design the time to make every minute together valuable to your collective experience, even any “unstructured” time.

  3. Design your agenda around outcomes. Help participants understand what's expected of them with clear objectives and session designs that lead to actionable outcomes or outputs. While this may sound obvious, we've seen countless agendas that list "topics for discussion" without clarity on the reason for the discussion (the same can be said for many regular meetings as well...)

  4. Create a safe space for conflict - and a mechanism for conflict resolution. Offsites are the ideal place for people to raise difficult issues and debate with one another. It's often how great teams tap their collective wisdom to find the best solutions to problems. Try to establish a safe environment where people can express their opinions without fear of repercussions. Just as importantly, be sure you have a mechanism to manage and resolve those conflicts productively.

  5. Keep the meeting on track. Nothing saps the energy of an offsite faster than two or three people “rabbit-holing” on a discussion that burns up valuable time and potentially pushes other items off the agenda altogether. Staying on track can be hard to do for smart and passionate teams, but it’s a critical discipline for successful offsites.

  6. Be realistic about what you can accomplish. One of the most common issues we see in offsite planning is “agenda bloat”. Teams (especially remote teams) that have not been together in some time can be tempted to stuff everything into a single offsite agenda. The best offsites are highly focused and outcome-driven; they create space for the kind of nuanced discussions that just don't happen on Zoom. If you have too many agenda items to discuss at a single offsite, it’s a good sign that you probably need to be doing them more regularly!

  7. Use a good outside moderator. We realize this may sound self-serving, but not only are outside moderators experts in all the points listed above, but they enable everyone to be a participant. Great moderators level the playing field, set a high bar for participation, and ensure that everyone in attendance is thinking and connecting at their best.

Want more help making sure your 2024 planning offsite is a huge success? Please book a discovery call


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