Working with 'problem' residents is a common challenge in medical education. This article describes a workshop designed to improve teachers' skills in this area as well as the results of an evaluation conducted to assess its effectiveness. Workshop modules focused on defining the problem, confirming the diagnosis, designing and implementing the intervention, and assuring residents' rights. Feedback on the workshop indicated that the participants were satisfied with the workshop content and format, and that they particularly valued the framework by which to analyze resident problems, gather relevant information, and design the intervention. Results on a self-assessment questionnaire indicated that the participants increased their knowledge in problem definition, data gathering, and the principles underlying an intervention strategy. This experience suggests that a two-day workshop focusing on the 'problem' resident can increase teachers' skills in working with 'problem' residents and can be adapted to diverse settings and disciplines.