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Training and retaining effective school principals entails understanding their trajectories into and through this position. The current study descriptively addresses the work trajectories of secondary school principals in Chile. Using census-type data and a longitudinal clustering method, we identified seven groups of trajectories underlying the overall trend in principals’ paths before and after assuming this role. Overall, we found that the trajectories of principals are dynamic and ever-changing. In Chile, these trajectories are unrelated to the school’s socioeconomic background and its type of administration. On the contrary, students’ high academic performance is highly relevant for principal stability in Chile. This trend aligns with the stability required by the most disadvantaged schools that achieve positive trajectories of school improvement.