A study was conducted involving the American Association of School Administrators (AASA) State Superintendents of the Year to gain information related to their perceptions and strategies for success and longevity. The study examined the factors of personal traits, school board relationships and current instructional issues such as No Child Left Behind and IDEIA to determine which, if any, contributed to their longevity and success of tenure. Surveys were mailed to all 150 State Superintendents of the Year, as identified by AASA. Descriptive were analyzed to examine trends and possible correlations. Strategies used to build board-superintendents relationships and deal with educational mandates, their perceptions of the effectiveness of their boards, the impact of educational mandates, and personal and professional characteristics of these superintendents were found.