Behavior analysts who supervise staff are responsible for establishing a healthy supervisory relationship and for teaching basic behavior analytic skills (e.g., verbal repertoires, technical repertoires, clinical decision-making). In addition, supervisors should prepare their supervisees to succeed in their subsequent professional activities by developing their interpersonal skills and professionalism repertoires. Difficulties in the supervisor relationship and problematic personal and professional skills often become the focus of targeted supervision efforts after the effects of deficits (e.g., avoidance of supervision, complaints from consumers, persistent tardiness) are detected. The primary purpose of this paper is to provide guidance to the supervisor's effort to identify and address barriers to successful supervision related to a damaged supervisory relationship and persistent interpersonal and professional skills of the supervisee. A secondary purpose of this paper is to act as a general call to supervisors to continually and thoughtfully reflect on their own history, repertoires, and behavior, such that they may continue professional growth as supervisors.