Context and leadership actions are closely related, and international research still contains little knowledge about which contextual conditions lead to which type of leadership action. In this study, school administrators? leadership was evaluated through multiple perspectives. The experiences of teachers, vice principals, supervisors, and school principals were examined by means of external, internal, and self-evaluations. We collected data from 25 participants using a semi-structured interview method and examined it with open coding, axial coding, and selective coding. As a result of the study, the contextual factors formed by national and local factors as obstacles and facilitators of school principals? leadership were revealed. We discussed the leadership actions regarding the theoretical, operational, and functional dimensions of school leadership.