The practice of grading students based on classroom performance has existed for centuries. Grading practices can look different depending on the division, school, or department. This study looked at lived experiences of school-based leaders around their preferred grading systems, how their preferences changed over time, and the impact their experiences and preferences had on the grading practices in their school building. School-based leaders were of interest because of the indirect impact they can have on teachers' grading practices (Hattie, 2012). Pre-service training around grading practices is minimal, leading educators to default to what they themselves experienced in schools. This can lead to negative outcomes for students as grading systems in use may measure more than just student achievement. The Transcendental Phenomenological methodology was utilized to gather data on school-based leaders' lived experiences. Data were collected through semi-structured interviews with nine school-based leaders from rural, suburban, and urban areas within the Commonwealth of Virginia. This study found that traditional grading practices continued to dominate in public education and that practitioners are rarely provided professional development or knowledge on alternative grading practices. Colleges and universities should create coursework around grading practices for future practitioners and school divisions and schools should provide professional development around research-based grading practices for all practitioners. / Doctor of Education / Students receive grades when they complete assignments and assessments in their courses. Grading practices have been around for over 400 years. Grading practices look different depending on the division, school, principal, and teacher. This study investigated the lived experiences of high school principals around the type of grading practices they prefer, how their preferences changed over time, and the impact of their experiences on grading practices in the high schools they lead. Principals are of interest because they can impact the grading practices of teachers, ultimately impacting students in the classroom (Hattie, 2012). Prospective teachers rarely receive training on grading practices in their university programs, causing most new teachers to default to what they themselves experienced in schools. This can be problematic as grading systems utilized by teachers often grade more than student achievement, including student behaviors, student effort, and student ability levels. A qualitative study was used to gather data on principals' lived experiences. Nine principals from the Commonwealth of Virginia were interviewed through semi-structured interviews. Three principals were from rural areas, three from suburban areas, and three from urban areas. This study found that traditional grading practices dominated in public education. Additionally, this study found that teachers are rarely provided training around research-based grading practices. Colleges and universities should create classes around grading for future teachers, while school divisions and schools should provide training around research-based grading practices for all teachers and administrators.