This article explores factors related to a transition to academic leadership from a faculty to an associate dean for academic affairs position within schools of social work, informed by a review of the literature on the role of the associate dean in higher education. The authors critically reflect on preparedness for the position and administrative leadership development in social work education, presenting case vignettes that highlight the challenges of navigating pathways from faculty to administrative roles. The authors conclude with the identification of opportunities, strategies, and offer selected recommendations to support the preparedness of the next generation of academic leaders in social work.