According to a sample of National Association of School Psychologists (NASP) members surveyed in 2015, roughly 5% of the association's members serve as administrators in a school system (Walcott & Hyson, 2018). For many, this career path evolves from a school psychologist role to a system-level administrator role supervising school psychologists, or overseeing social-emotional learning initiatives or other prevention or crisis response programs. In smaller districts, an administrator may wear all of these hats, plus supervise other staff such as related service providers. The 2015 NASP member survey noted that still others were in broader leadership roles, such as community agencies or state departments of education. The authors point out that this percentage likely underestimates the number of school psychologists who are in administrative positions as the survey sampled current NASP members only, and it is likely that some school psychologists engaged in nontraditional roles have not maintained their NASP membership. This article will highlight key concerns regarding the lack of clear professional guidance for administrative supervisors, issues of liability, distinctions between various supervisory roles when supervising certified staff (e.g., administrative supervision, clinical supervision, case consultation), blurred lines regarding best practices versus standards of care, and the responsibility, but complexity of supporting implementation of evidence-based practices.