In most districts, the evaluation of superintendents by the members of the board of education takes place in executive session of the board behind closed doors. Few board members or superintendents question the status quo. Most evaluation forms are merely collections of subjective checklists that catalog approved personality traits, attributes, and behaviors. Although the questions may appear objective, the answers are inevitably and subjective opinions of five individual board members about whether and to what degree the superintendent exhibits desirable traits or engages in approved activities. In essence, when the subject of superintendent evaluation is the superintendent herself or himself, any assessments and judgments by board members, positive or negative, objectively expressed or not, can seem intensely personal. Given these conditions, it is no wonder that all parties prefer to keep the process as private as possible. Yet, if the ultimate purpose of evaluation is improved school district performance, a great deal is lost when so much time, energy and frequently emotion is expended on what seems little more than a personality inventory of the superintendent. In this article, the authors describe how their district has transformed the superintendent assessment process from focusing principally on the individual to focusing on the performance of the district as a whole.