Purpose: In an era of increased autonomy and accountability in education, school principals have been given the responsibility for many tasks that used to be centralized, such as hiring and managing personnel, ensuring that the curriculum is followed and that the development of the school is on the right path. In this study an exploration is attempted into the associations among institutional context, school leadership, school climate and student outcomes. Design/methodology/approach: The authors analyze data from the Programme of International Student Assessment study 2015 to identify variations in institutional context (autonomy and accountability) among education systems to determine whether and how institutional context is associated with leadership and whether education systems, in turn, are associated with school climate and students' achievement in reading. To account for the hierarchical structure of the education systems under investigation, a three-level structural equation modeling (SEM) approach was employed to analyze the data gathered on the institutions, schools and students. Findings: No association was found between the degree of autonomy of an education system and leadership behavior; however, accountability and leadership seemed to go together. Achievement in reading competencies was greater in school systems in which principals had more autonomy. At the school level, a relationship was found between leadership and opportunities for parental involvement. Originality/value: The results of this study indicate the need of strong leadership in order to have better results when there is more accountability. In this sense, the authors' findings also point to the increased importance of context-sensitive leadership skills.