The practice of grading students began in the late 1800s and became institutionalized within the educational system. Grading in K-12 education has remained relatively unchanged in its purpose, intent, and use for nearly a century while simultaneously becoming an increasingly critical factor that impacts student opportunities, external perceptions of student abilities, and student self-efficacy. While researchers have analyzed many facets of grading, what has widely not been studied is the influence that educational leaders have on grading practices. Shields (2018) posited that in the current age of education, transformative leadership is necessary to challenge knowledge frameworks, enact moral courage, and redistribute power. Thus, this dissertation examines the perceived or actualized influence the school-site educational leader has on enacting grading practices that address student learning. I interviewed fourteen public high school principals in the United States to investigate their perceptions of grading practices that currently exist, the source of their influence over grading, and the role they play in upholding consistent and reliable grading practices that promote student learning. The interviews revealed three overarching themes. First, participants identified that external and internal influences hold power over grading practice implementation in positive and negative ways. Second, principals identified that there is a distinct dichotomy that exists between grading, assessing, and learning. Finally, participants shared that there are many power pressures that police action and drive inaction with grades that often hold them accountable while also regarding them as powerless. These findings show that the necessary consensus needed for a common approach to grading is absent; the quality and support of equitable learning is being sacrificed at the altar of institutionalized grading; the system and stakeholders are frustrated, conflicted, and confused; and power driving the use grades is being actively brokered. However, despite each of these concluding findings, this study also demonstrated that the way forward with equitable grading (Feldman, 2024) demands learning to be recentered so that inequitable grading doesn't sit as the dominant narrative and learning and grading can represent what students actually learn. School site educational leaders that utilize Shields' (2018) transformative leadership can brokerage and leverage their power with their upper leadership, teachers, families, students, and amongst their communities. [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.]