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This study examines collective leadership development of teachers and administrators in three high schools in urban, suburban, and rural districts through the lens of an analytic model development model. Data over the course of two years were collected from each of the three high schools and consisted of interviews with teacher and administrators (n=64), document analysis, and observations for a multiple-case study design. Schools’ efforts to develop leadership were dependent on five major elements and influenced development activities and experiences that determined outcomes. Variations in the antecedent factors were associated with differences in development experiences and outcomes in all three contexts. This study has implications for how schools and districts understand both formal and informal leadership development.