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This study examines how principals’ autonomy shapes their roles as street-level managers, bridging strategic goals and operational demands in precarious institutional contexts. A longitudinal qualitative design involved interviews with 14 Chilean principals over three years, analyzed using grounded theory. Findings reveal how, during the implementation of the Chilean New Public Education Law, principals responded to unclear guidelines, community demands, and weak middle-tier support through three adaptive strategies: Collective Influence to strengthen systemic impact, Territorial Networks to secure resources, and Pedagogical Improvement to sustain educational quality. These findings underscore the evolving role of principals in policy implementation and highlight the need for longitudinal research on their adaptive strategies and influence on educational reform.