This is a follow-up article to an action research study that explored the effects of an imagery intervention on an elite rugby union player conducted over a 14-week period during the competitive season (Evans, Jones, & Mullen, 2004). A key feature of the study was that the same individual fulfilled multiple roles, specifically those of trainee sport psychologist, coach, and researcher. The aim of this article is to explore, from a trainee sport psychologist’s perspective, some of the issues that resulted from fulfilling multiple roles, both in the context of the study and in professional practice generally. The issues that emerged were consistent with the dual-role literature and involved role conflict surrounding areas of responsibility, scientific evidence versus social validity, confidentiality versus public statement, and the interpersonal welfare of both athlete and coach-sport psychologist (Ellickson & Brown, 1990). The findings highlighted (a) the importance of establishing ground rules (and planning), (b) the intensified emotional demands placed on the multirole practitioner, (c) the importance of involving a critical friend or outside agent, and (d) the potential for role conflict and the threat to objectivity.