Professionalism remains a substantive theme in medical literature. There is an emerging emphasis on sociological and complex adaptive systems perspectives that refocuses attention from just the individual role to working within one's system to enact professionalism in practice. Reflecting on responses to professional dilemmas may be one method to help practicing physicians identify both internal and external factors contributing to (un) professional behavior. We present a rationale and theoretical framework that supports and guides a reflective approach to the self assessment of professionalism. Guided by principles grounded in this theoretical framework, we developed and piloted a set of vignettes on professionally challenging situations, designed to stimulate reflection in practicing physicians. Findings show that participants found the vignettes to be authentic and typical, and reported the group experience as facilitative around discussions of professional ambiguity. Providing an opportunity for physicians to reflect on professional behavior in an open and safe forum may be a practical way to guide physicians to assess themselves on professional behavior and engage with the complexities of their work. The finding that the focus groups led to reflection at a group level suggests that effective reflection on professional behavior may require a socially interactive process. Emphasizing both the behaviors and the internal and external context in which they occur can thus be viewed as critically important for understanding professionalism in practicing physicians.