This article examines how school trustees (i.e., elected school-board members) conceive of their own leadership role and work with other levels of leadership within school districts. In a mixed-method study, a total of 121 school trustees were surveyed and 12 were interviewed across Ontario. A framework is proposed to better understand the tension in the competing and conflicting leadership roles of trustees. Furthermore, even though all school districts operate under the same policy and legislative framework across the province, the framework captures the two very different models of working with school-district management reported by trustees in this study.