What qualifies an educational leader to lead a school (or schools) in and for a democratic society is more than simply a set of skills. One must also consider dispositions, attitudes, and traits that, if they cannot be taught, might yet be identified and nurtured in budding and practicing leaders. One of the most important objectives of an educational leader's education is the leader's ability to undertake a critical social contextual analysis tied to a liberatory, emancipatory, or at minimum a social and personal developmental educational philosophy. Without a critical social analysis, the author argues that students, teachers, administrators, other educational leaders, concerned citizens, and policy makers are likely to simply accept and work to maintain the status quo. Having the skills that permit a critical social analysis enables the leader--be she/he an administrator, student, teacher, or parent--the capability to lay bare the particulars of a certain situation, context, or milieu, and recognize just who is privileged and who is not.