Five Questions to Ask When Planning Off-Sites and Retreats

From Paula Wilder, senior partner at WilderWeber Leadership Group, a VT KnowledgeWorks member company:

Gardening is such a great metaphor for organizational life.  I have started the Spring search for trees to replace the ones I removed last Fall.  After years of gardening mishaps, however, I have learned that the most important part of planting is not finding the plant, but preparation – selecting the right location and the right soil.  The old wisdom is true: "Better to have a $5 hole for a $1 plant than a $1 hole for a $5 plant.”

A leadership retreat tip from Paula Wilder The same kind of thinking applies to effective retreats, off-sites and meetings.  What needs to happen to ensure the work takes root and thrives?   For plants, it’s carefully considering the right growing conditions.  Once the plant is in the ground, it is about on-going care.  It’s pretty much the same with people I think:  What are the productive growing conditions the group will need to sustain the work?

Here are five questions that usually generate great conversations when planning an off-site or retreat:

  • How can participants be engaged in co-designing the retreat? 
  • What valid information is needed to enrich the conversation?   
  • How can clear, collective commitment be generated? 
  • How can group effectiveness best be enhanced? 
  • What new leadership behaviors are required for the future? 

When I think about what happens after the retreat, I picture the newly planted trees securely tied to wooden stakes to keep them from being up-rooted or over-turned. For groups, the question worth asking is, "What kinds of structures and supports are needed so that the high spirits and great plans generated at the retreat withstand the gusty forces of the status quo?"

If you have ideas about how to make sure retreat action plans get traction, we would love to hear about them.  Please email us at [email protected].  We will post your ideas on What's New.

"Leadership Retreats and Off-sites: Cultivate the Soil" is the second in a series of three leadership retreat tips from Paula Wilder. The first is Leadership Retreats and Off-sites: Retreat in Order to Advance.

Paula Wilder is an organizational effectiveness expert and senior partner at WilderWeber Leadership Group.  WilderWeber Group is a VT KnowledgeWorks member company in Blacksburg, Virginia.

You're invited to learn more about WilderWeber Leadership Group on Inside VT KnowledgeWorks.  This post originally appeared on Handshake 2.0


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