This qualitative study explored the transition from teaching to administration through the voices of four novice vice-principals. An integrative approach was used to capture the interaction between new vice-principals, their external contexts, and the resulting leadership outcomes. The data revealed that in spite of these new administrators' intention to create better schools for all students, they encountered multiple factors that hindered their ability to achieve their leadership goals. Key obstacles included the ambiguous legal and institutional configuration of the vice-principalship, inadequate preparation for challenging front line managerial and disciplinary roles, and inappropriate transitional support. Through listening to new vice-principals voices and providing relevant preparation and coordinated supports, school districts, policy makers, professional associations, and regulatory bodies can improve this transition and address some of the leadership challenges facing schools.