Interscholastic athletics represent the most significant body within the sport industry (Fraina, Forsyth, Johnson, & Whisenant, 2022) given the lasting positive outcomes that can be enjoyed by student-athletes through their participation. With the impact of head coaches, both positively and negatively, in shaping the achievement of these benefits (Adeyemo, 2022; Gould & Carson, 2010), athletic directors must be able to ensure that the most effective individuals are leading athletic programs within their high school athletic department. Existing research has taken a quantitative approach to determine the presence of coaching evaluations within high school sports (Hill & Pluschke, 2005; Hoch, 1989; Thielges, 2015); however, a gap in the literature exists related to a more thorough understanding of the perspectives and experiences of athletic directors when leading the coaching evaluation process. Therefore, the purpose of this qualitative study was to analyze how interscholastic athletic directors utilize the performance appraisal process to evaluate the effectiveness of head coaches. Three theoretical frameworks (i.e., performance appraisal process, goal setting theory, and stakeholder theory) formed the foundation on which the research questions were developed. In total, 25 participants were secured that represent athletic directors across school classification (i.e., 1A, 2A, 3A, and 4A) and school type (i.e., public and private), with saturation achieved through this sample size. Data collection methods included both semi-structured interviews and document analyses of coaching evaluation forms. Through a thematic analysis, seven main themes (i.e., elements of the coaching evaluation process, role of head coaches, coaching evaluation form, key goal areas, main stakeholder groups, leveraging stakeholder feedback, and challenges in maximizing coaching evaluations), which include 32 subthemes and 53 sub-subthemes, emerged that provide deeper context into the key shared elements present within coaching appraisals in high school sports and describe how athletic directors engage in this process to examine coaching efforts. Practitioners can consider the findings from this study to reflect on and strengthen their own evaluation processes to ensure the most effective appraisals have been developed within their athletic department when reviewing the performance of head coaches. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]