Cody Miller was asked to present on a panel with a fellow doctoral student and a current principal at a local elementary school for a social justice and diversity in school leadership course. Miller's experience on the panel became an informal type of capstone experience as he found himself having to argue and defend social justice teaching practices in front of a room full of current or aspiring principals. This article applies a critical lens to his experience as a guest speaker in order to unearth assumptions made about teachers from current and future administrators. He uses this perspective to problematize administrator attitudes about teacher quality and evaluations. Three major themes emerge from his writings and provide the structure for this article: the influence of master myths over school leaders, the perpetuation of gender norms within school leadership, and the unexamined institutional power school leaders hold over teachers.