Essay · 14 min read

How to Plan a Great Team Offsite

Matt Munson · Matt Munson (2x exited founder, CEO coach) Free Intermediate

Written by a two-time exited founder who now coaches CEOs, this maps almost exactly onto our answer: split business focus (financials, strategy, goals) from people focus, do the hard thinking when brains are fresh, and hold the agenda loosely because things going off-track usually means you hit the good stuff. His fix for the 'expensive vacation' trap is concrete: hire a facilitator so you can be a participant, and use guided journaling to pull what is actually in people's heads into the room.

  • If you suspect you have too many goals on the agenda, you do; cut it and put the important stuff up front
  • Hire a facilitator so leaders can be present participants instead of managing the clock and the agenda
  • Skip forced team-building; connection comes from shared new experiences, partner walks, and open conversation
Open on mattmunson.medium.com ↗

The question it answers

  1. How do I run an offsite that actually pays for itself instead of being an expensive vacation?

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