Medical professionalism is increasingly recognized as a core competence of medical trainees and practitioners. Although the general and specific domains of professionalism are thoroughly characterized, procedures for assessing them are not well-developed. This article outlines an approach to designing and implementing an assessment program for medical professionalism that begins and ends with asking and answering a series of critical questions about the purpose and nature of the program. The process of exposing an assessment program to a series of interrogatives that comprise an integrated and iterative framework for thinking about the assessment process should lead to continued improvement in the quality and defensibility of that program.