The educational reforms underway in Indonesia include the restructuring of requirements for the training and appointment of school principals to increase their quality and diversity. One of the goals of these changes is to remedy the under-representation of women in educational leadership. This goal recognizes the need for women leaders to be role models and advocates for female students, for women’s voices to be heard in educational decision making, and for equal career development opportunities to be available to men and women in the Indonesian school system. National and district-level statistics and the findings of interviews with 76 male principal administrators in 15 school districts across Indonesia are used in this chapter to identify the traditional paths to principalship. The barriers encountered by women who aspire to leadership in Indonesia’s diverse cultural and religious environment are examined, and consideration is given to strategies for overcoming these barriers by implementing new requirements for principal training and appointment.