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High school graduation rates and the leadership of principals are important measures of accountability within schools. Principal leadership has been investigated through qualitative and correlational studies in mostly urban areas. Limited research has focused on the educational leadership characteristics of the high school principals and graduation rates in rural areas. The purpose of this study was to identify, describe, and categorize the leadership characteristics of veteran and novice principals with respect to graduation rates in selected rural schools. Bolman and Dealâ??s 4 frames of leadership informed this study and helped to create the broad leadership categories of interpersonal skills, leadership and communication styles, and collaboration skills. The research questions focused on understanding the leadership characteristics and differences between novice and veteran principals. Purposive sampling was used to select 21 participants for in-depth interviews in 7 high school settings. The methodology combined interviews with a review of district data and documents. The data were thematically analyzed by a constant comparative method and category construction. Trustworthiness was ensured with member checking and triangulation. Key findings indicated that all principals had general leadership characteristics such as active listening, collaboration, a communication style, and promotion of school/home partnership. Three out of 4 high graduation rate schools tended to have veteran principals. Veteran principals focused on professional development and cultivating relationships, whereas novice principals focused on using data in decision making. Identifying and developing specific characteristics in leaders and matching them with schools will improve the instructional environment for students and strengthen the expertise of the faculty and staff.