Making a list and checking it twice

Over the years I have really moved away from doing the standard kinds of strategic planning meetings that most every organization seems to do.  I recognize the need for management, but I see many organizations either get locked into a control mindset that limits their options, or create huge lists of things to do that can’t possibily be accomplished.  I am rather inclined to work with organizations that are trying to find ways of becoming strategically adaptable, but most organizations I work with are already there.

Today though I received a call from an organization that I like, that does good work, but are locked into a really traditional set of dynamics about control, managements, roles and responsibilities and planning.  We are planning a two day strategic planning retreat to, as I put it, “make a list and check it twice.”  That is to say that the result of this gathering should be a prioritized work plan.

I don’t want to cast aspirations on the organization, but I sense that bringing a new participatory and strategic adapatation persepctive to planning will be a difficult thing to do all at once.  And so I’m up for some ideas.

This is a small organization that is part community organization and part infrastructure development.  They are governed by an excellent and experience Board of Directors who operate out of fairly traditional governance worldviews.  Their senior staff are longstanding, but they are growing and needing to make some transition plans.

Everyone likes each other well enough and they do good work, so I think the opportunity to spend two days in creative work would be welcome.  I don’t want to sit around a Board table and make a list, but I do want to them to get what they need from the retreat.  I thought I’d ask here, sort of as a public service, because many of us in the world of consulting and facilitation get these kinds of requests, and the same old same old doesn’t always work.

So, hivemind, what are some ideas you all have for helping a small and important organization do some strategic work planning in a new and interesting way?