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Schools need effective leaders. Research demonstrating the importance of effective educational leadership has grown substantially in the last decade. However, limited research exists on leadership practices in Jewish day schools and the conditions for school leader success. This study had two goals: (1) To develop and validate a measure of leadership behaviors in Jewish day schools; and (2) To identify contextual factors that influence leadership behaviors, such as community relations, leaders’ workload, and professional development. Survey administration with more than 300 school leaders demonstrated good psychometric properties. Multivariate statistical analyses and follow-up interviews revealed several conditions that influence leadership behaviors including relations with teachers, parents, and community-based organizations, professional development, autonomy to make decisions, and a school leadership team.