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Recent scholarship studying the role of educational leaders fostering greater inclusion for students with disabilities has been directed mostly at the principalship, yet comparatively little attention has been paid to the role of district-level special education leaders (DSELs). These leaders are nominally responsible for the education of students with disabilities in their districts, are familiar with the complexities of special education law, policy, and practice, and often engage in similar administrative work to that of general education leaders. This study examines how DSELs attempt to foster greater inclusion for students with disabilities and the leadership challenges they face in this work. The results highlight the importance of contextual factors that influence how leaders create a more inclusive environment.