The position of superintendent has long been characterized by high rates of turnover. The purpose of this study was to examine the factors that influence the anticipated length of service of the current superintendents in a Midwestern state. It examined superintendent responses to determine trends affecting length of tenure. The findings of this study showed a disconnect in superintendent recognition of the most challenging aspect of the position. While current superintendents overwhelmingly recognize the importance of relationships, they tend to put less effort into strengthening their relationship with the local school board. As such, deterioration of that relationship leads to the most frequently reported rationale for superintendent departure from a district. Additionally, the study determined that the most significant factor that would convince young superintendents to remain with a school district is offering an increase in compensation. Some turnover is expected given the age of many superintendents as they ascend to the position, but with an influx of young district leaders it is crucial that school boards offer assistance monetarily and through training and recognition of the importance of relationship to successful district tenure.