The assistant principal plays a key role in school success but research suggests there are differences between principals and assistant principals in their perceptions of their roles. The 2011 Teaching, Empowering, Leading, and Learning Kentucky survey responses of educator perceptions were statistically analyzed for the statewide sample of principals and assistant principals. Results indicate that principals and assistant principals reported significantly different perceptions regarding teacher leadership and school leadership. Differences in principal and assistant principal responses were not related to student achievement, however. Implications for collaborative engagement between principals and assistant principals as they focus on increasing school leadership and teacher effectiveness are discussed.