Leaders in health professions schools are evaluated regularly and offered faculty development opportunities to foster excellence in their roles. Nevertheless, there is a surprising dearth of information available on the specific topic of evaluating leaders. While the evaluation of leadership behaviors and outcomes would seem to be an essential component of leadership development, this topic is notably under-represented, particularly in the health professions literature. Consequently, identifying and employing best practices in leadership evaluation becomes a significant challenge in both health profession schools and hospitals. In this chapter, we first comment on existing leadership frameworks found within the health professions literature. We then suggest that a comprehensive approach to evaluating leaders must take place at four levels: personal, interpersonal, team, and organizational. We conclude with specific recommendations concerning a variety of methods one can use to evaluate leaders.