New administrators in urban schools face enormous challenges. The novice leaders in this study are graduates of a preparation program at UC Berkeley, and are participants in a leadership induction program. This research examines one aspect of their new position--disciplinarian--through the lens of leadership stories. Although the middle manager disciplinary role presents challenges for new administrators, it is a requirement of the position. New administrators are typically student advocates in this arena, but experience difficulty interacting with teachers and other adults responsible for discipline. Their use of the legal and punitive language, now common in schools, tends to reinforce the current systems. They often challenge the disciplinary systems on a case-by-case basis or alter parts of it, but do not interrupt the overall procedures for carrying out discipline. Finally, they are conflicted about their new identity as enforcer in this role, and experience frustration in navigating the discipline territory.