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As systems thinking has been considered an effective means of dealing with diverse problems, this study explores the developmental process of systems thinking among school principals. Data were collected among prospective, novice and experienced principals via 82 interviews, 6 focus groups and 27 observations. Data analysis was conducted by generating themes through an inductive process of condensing, coding, categorizing and theorizing. Findings indicate that the development of systems thinking among school leaders consists of five stages: (1) pre-service stage; (2) survival stage; (3) consolidation stage; (4) role maturity stage; and (5) possible decline stage. These findings expand on the limited knowledge about systems thinking in school leadership, and may assist in finding ways to accelerate it among school leaders.