The ever-changing and complex nature of school leadership requires schools to have principals who have strong leadership skills and experience. In this study, the researchers sought to define the essence of effective principals through the lens of their supervisors. Using phenomenological inquiry, we interviewed four assistant superintendents of large school districts in the Greater Houston area. These supervisors, who supervise several school principals, believe successful principals are passionate, driven leaders with well-developed leadership and communication skills who can accurately assess the school culture and the level of teacher buy-in. Implications for training principals and future research are shared.