This study explores how school principals perceive subversiveness and how they exercise subversion to transform policies, regulations and practices that they believe are counterproductive. This qualitative research employed semi-structured interviews with 18 elementary and secondary school principals in Metro Vancouver. Role theory was used to guide the inquiry and data analysis. Research results show that school principals have mixed feelings towards subversiveness given its negative political connotations. Although the negative image seems to go against the normative role expectations of school principals, this does not deter principals from the attempt to exercise subversiveness when they think it is good for their students. Principals have employed various strategies in their subversive activities in order to succeed at their work. This study suggests that leadership is essentially a subversive activity from which change occurs.