This paper discusses how social workers with a primarily clinical education and field experience can best transition into administrative roles in social work agencies. This exploratory investigation grew out of a review of relevant literature and informal interviews with four administrators with extensive clinical experience. It presents both the beneficial overlap between administrative and clinical work that enhances administrative competence and the challenges faced by transitioning clinicians. The paper concludes by presenting a range of strategies that transitioning clinicians can use to manage these challenges, as well as encouraging social work education programs to emphasize and provide increased training of both clinical and administrative methods to social work students, no matter what their specialization.