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Although there is a substantial body of literature on school leadership, few studies have examined how change in leadership is related to school improvement. Also less well studied is the influence of contextual conditions on how organizational processes evolve, to constrain or augment school outcomes over time. Here, we use moderated-mediation analysis to examine how change in principal leadership is related to achievement growth, mediated via change in multiple organizational processes. We examine how these mediational relationships are moderated by initial school conditions. We find that improvements in school leadership are related to learning gains only through improvements in school climate. The size of this relationship is similar regardless of initial school leadership and initial school climate.