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Chile, as in many countries around the world, has implemented policies for principal recruitment, development and retention. The objective of the current study is to examine principals’ perspectives on policies implemented in Chile with the aim of making principalship a more attractive job. Data are drawn from an online survey with responses from 579 practicing and 158 former principals and in-depth interviews with 25 former principals. The main findings show that policies that directly improve working conditions are deemed effective but in need of improvement. A leadership career pathway and policies to diminish administrative work are suggested. This study contributes to evidence-based policymaking by drawing from the insights of practitioners.