This mixed methodology study explored the reasons that teachers in Israel are motivated to become school leaders, and the relative importance of the different discouraging factors that worked against such interest. A cross-national Israeli survey included 39 individual interviews, 2 focus groups of 25 teachers each, and a questionnaire completed by 149 teachers working in Jewish schools. Findings indicate a sense of mission and personal challenge motivated our sample. The most significant discouraging factor was the perceived inability to circumvent bureaucratic constraints imposed by the Ministry of Education. Implications and reform efforts for reducing bureaucratic constraints upon school leaders are discussed.