The purpose of this ethnographic case study is to provide a rich picture of the ways in which the multidistrict superintendent (MDS) engages in contextually responsive and place-conscious leadership across multiple community school districts. Secondarily, the research explores the meaning ascribed to these leadership practices in the form of participant-generated metaphors. We find the MDS employs the metaphors of weatherman, cow herder, and river guide to explain practice as he negotiates tensions of place-consciousness with his goal of a common vision for the multidistrict union.