One of the primary responsibilities of the school board is to regularly assess the performance of the superintendent.Therefore, most states recognize the need for school boards to review the superintendent’s performance annually. However, many school board members have no experience in the area of performance evaluation (DiPaola, 2007; TASB, 2007). Kowalski (2005) states that school boards have three primary responsibilities: “(a) assure that state laws, rules, and regulations are followed; (b) establish policy in areas not covered by state laws, rules, and regulations; and (c) employ a superintendent to serve as chief executive officer (CEO)” (p. 11). Michael DiPaola in his 2007 article on superintendent evaluation stated the following: “Superintendents’ performance evaluations continue to be too frequently conducted through a highly informal, subjective process, based more on impressions than data.” Superintendent evaluation requires a real commitment of time and energy to overcome the traditional obstacles that exist. Lack luster superintendent evaluation can be overcome by a sound evaluation process that serves the best interest of the students and schools of the district that is constructed around reliable and valid data free from bias and where school board members are fully informed about the evaluation process and how superintendent evaluation is different than any other type of evaluation. In the end, the key to a district success is the school board-superintendent relationship and a well done evaluation process preserves this relationship.