This research examined secondary administrators’ perspectives about the expression “the best interests of the student.” Principals’ intimate reflections provided empirical insights into what they mean when they use the expression, “the best interests of the student” and whether such a common catch phrase could provide ethical guidance. A modified phenomenological research method suited for an educational research context was used to capture administrators’ perspectives and experiences. Results challenge the theoretical notion that the expression, “serve the best interests of the student” is, or should be, used in some primary, rule-based first order manner by administrators to inform their ethical decision making. Ethical judgment was more complicated and contextually defined than following a fundamental professional injunction, but the expression resonated with administrators, typifying dispositions that promote moral practice. Results and interpretations bring conceptual clarification to the moral leadership construct “serve the best interests of the student.”