Leadership is a critical strategic variable within program management as a process that can motivate employees and influence agency performance. Specifically within the field of vocational rehabilitation (VR), there has been little study of the dynamics of leadership and how these influence the agency, employees, and clients. To date, much of the leadership-related research has focused on clinical supervision, yet there remains a need to continue to build the supervision literature base and to broaden the view of leadership to include the conventional strata found in VR agencies: administration, supervision, and direct service (aspiring leaders) levels. The current study outlines a more comprehensive model of leadership within state VR agencies and then explores administrator’s perceptions of important leadership components, needs for further development, and expected vacancies at each level. The findings reveal expectations of high turnover among senior leader positions over the next 5 years, specify important elements of leadership at each level, and identify numerous needs which are not being adequately addressed through current systems. These results hold value in promoting general understanding of leadership functioning in rehabilitation agencies, informing the design of targeted professional development programs, and establishing improved succession planning across organizations.