Abstract The shift to using outcomes-based competency frameworks in medical education in many countries around the world requires educators to find ways to assess multiple competencies. Contemporary medical educators recognize that a competent trainee not only needs sound biomedical knowledge and technical skills, they also need to be able to communicate, collaborate and behave in a professional manner. This paper discusses methodological challenges of assessment with a particular focus on the CanMEDS Roles. The paper argues that the psychometric measures that have been the mainstay of assessment practices for the past half-century, while still valuable and necessary, are not sufficient for a competency-oriented assessment environment. New assessment approaches, particularly ones from the social sciences, are required to be able to assess non-Medical Expert (Intrinsic) roles that are situated and context-bound. Realist and ethnographic methods in particular afford ways to address the challenges of this new assessment. The paper considers the theoretical and practical bases for tools that can more effectively assess non-Medical Expert (Intrinsic) roles.