Competency in moral Literacy, like any other literacy develops through careful and continual practice (Herman, 2007). In this qualitative study we explore the vice principalship and the development of administrative moral literacy. Using a northern Ontario Canada case study, we recount how three secondary school vice principals further their own moral literacy through the execution of their professional role--specifically, how such practices as professional decision making, self-reflection and the use of personal self messaging can ameliorate moral literacy competency. We used both interviews and job-shadowing to investigate how participants navigated the challenges of the vice principalship, and how participants defined and measured success. We analysed stories and metaphors (Clandinin and Connelly, 2000; Seidman, 2006) to identify specific skills and strategies in the formation of moral literacy, such as a sense of moral purpose, self-knowledge and self-regulation, flexibility, vision and a high tolerance for ambiguity.