Shanna Ratner of Yellow Wood Associates, Inc. was invited by the Northwest Area Foundation of St. Paul, Minnesota to work with grantees receiving support under its Regional Center Initiative. Grantees received significant financial support to prepare strategic plans designed to reduce poverty in their geographic areas, which are mostly rural. Ms. Ratner worked with grantees to explore what it means to think strategically in the context of community economic development using the personal experience of participants and an analogy to the game of chess. Participants also considered three key roles in plan development and implementation and who would play these roles in their plans. Key roles include strategic thinkers, doers, and pollinators (people whose job it is to learn from the efforts of doers and convey the learning back to the doers and the strategic thinkers). Follow up work was scheduled with several workshop participants.