The shortage of school leaders, mainly caused by the growing complexity of the job is steadily growing in recent years. This study reports on the results of a comparative empirical study into the causes of premature departure for male and female principals in primary and secondary education. Principals who have experienced premature departure themselves served as respondents. The risk factors for premature departure were researched in four areas: the school organization, the working environment including the school culture, the selection procedure and the principal him or herself. The results showed that the causes of premature departure are a combination of factors that are embedded in the context in which the leadership is performed and personal characteristics of the principal.