This study investigated the effects of special education background and demographic variables on the perceptions of leadership styles by public school principals with and without special education backgrounds in Massachusetts. Utilizing Q-sort methodology, principals sorted 47 statements reflective of transformational, instructional, transactional, and distributed leadership. Analysis found that the participants separated into two factor groups. The special education background of the participants did not influence the formation of the factors, and it was found that prior special education experience was not a predictor of subsequent leadership perceptions of principals. Instead, Factor A was composed of younger, less educated, less experienced principals in lower-performing schools who valued instructional leadership and school improvement in their leadership. Factor B was composed of older, more educated, more experienced, and more ethnically diverse principals who worked in higher-performing schools and who valued multiple leadership styles and high-level, whole-school leadership. A model was developed, showing a process for how principals grow their expertise and evolve their leadership over the course of their leadership careers. This study demonstrates the importance of continued research into special education leadership and of how leadership is differentiated among schools with different levels of student performance.