Within the education field evaluation exists on many levels. In a school district it is routine to find superintendents evaluating principals, principals evaluating teachers, teachers evaluating student work and parents evaluating all aspects of the school community. The purpose of this study was to investigate the manner in which public school superintendents perceived that they evaluated principal performance. The eight participants in the study were Massachusetts public school superintendents. The superintendents originated from districts located in eastern Massachusetts. Participants were interviewed about their principal evaluation activities and asked to provide documents relevant to the ways in which they evaluated principals. This study was specifically focused on three research questions. The first question dealt with the types of criteria and evidence a superintendent considered when evaluating a principal. The second question dealt with the processes and practices a superintendent employed to determine the degree to which a principal met the aforementioned criteria. The final question dealt with the level of consistency between principal evaluation practices advocated in the literature and the actual practice of evaluating principals as conducted by this study’s participants. The findings of this study indicated that principal evaluation is an incredibly complex endeavor. The study also identified several areas in which the principal evaluation can be strengthened in order to enhance principal leadership. The identified areas included the articulation of principal evaluation activities that are more cognizant of the local school environment, the need to better assist beginner superintendents as the evaluate principals and the need to provide superintendents with more time to thoroughly evaluate principal performance.