No More Middle Seat Meetings
4 Tips for Offsite Meetings You Don’t Want to Forget
We know – there are some things kind people don’t do intentionally:
They don’t book a middle seat for fun.
They don’t reheat fish in the microwave at work.
They don’t watch videos in public with the volume up.
They don’t voluntarily hop on a 5:50 a.m. flight to spend 11 hours in the American Airlines lounge at O’Hare. (Guilty – 3/16/26)
When these things happen, they cause all of us to question the sanity and decision-making ability of the people around us. And rightly so.
There are moments when we are so busy, so wrapped up in our daily lives, that we forget key details that make all the difference.
Over the past 15 years, the team at Insight has facilitated hundreds of offsite leadership meetings. We’ve identified four patterns that foster productive meetings.
1) Clear Goals: Before every offsite, we ask the leader: What’s your goal? We get it – bringing your leadership team from all over the country to one location is a feat of strength even Chuck Norris would be proud of. But we also need to maximize the time everyone spends together.
What is your goal?
What do you need to accomplish?
What will make the offsite a success?
2) Camaraderie: Healthy and effective teams spend time together outside of the conference room and take time to get to know one another during the meeting itself. Trust is built through positive experiences with one another. Relaxing team dinners, giant shuffleboard games, and riding Bird scooters through the city can help teams find common ground and work more effectively together. We have led groups through escape rooms, Top Golf, building bikes for foster children, and fun evenings on the town.
Build in something relaxing and enjoyable so the team can connect. When teams build trust outside of the boardroom, they make better decisions together in the boardroom.
Build time into the meeting for team members to share something personal – not just professional. This can be about family, favorite restaurants – anything to help establish a connection.
3) Space: When everyone flies in, the tendency is to overfill the agenda and rush through it. We recommend capitalizing on the time together to work on alignment, innovation, and problem-solving rather than status updates better handled on Zoom. Leave space for effective challenge and dialogue to help improve the team.
4) Development: Effective leadership training and facilitation can help a team align, grow, and think through what’s next. We have led teams through creating team charters, practicing healthy challenge, working through communication exercises, and leveraging assessments to help everyone know how to work together and play to their strengths. When the topic aligns with the goals of the offsite, the training can add energy, camaraderie, and cohesion in ways that regular meetings often miss.
We know that no one planning an offsite intentionally skips these steps; we also know that no one wants their offsite to remind someone of sitting in the middle seat on a long flight. Shoot a reply to this email if you have a question or need to bounce an idea around.
Heads up: We’ve stepped into offsites with as little as two weeks’ notice and as much as twelve months’. It’s never too late to call.
