We report on our experience with an approach to debriefing that emphasizes disclosing instructors' judgments and eliciting trainees' assumptions about the situation and their reasons for acting as they did. To highlight the importance of instructors disclosing their judgment skillfully, we call the approach “debriefing with good judgment.” The approach draws on theory and empirical findings from a 35-year research program in the behavioral sciences on how to improve professional effectiveness through “reflective practice.” This approach specifies a rigorous self-reflection process that helps trainees recognize and resolve pressing clinical and behavioral dilemmas raised by the simulation and the judgment of the instructor. The “debriefing with good judgment” approach is comprised of three elements. The first element is a conceptual model drawn from cognitive science. It stipulates that the trainees' “frames”—comprised of such things as knowledge, assumptions, and feelings—drive their actions. The actions, in turn, produce clinical results in a scenario. By uncovering the trainee's internal frame, the instructor can help the learner reframe internal assumptions and feelings and take action to achieve better results in the future. The second element is a stance of genuine curiosity about the trainee's frames. Presuming that the trainee's actions are an inevitable result of their frames, the instructor's job is that of a “cognitive detective” who tries to discover, through inquiry, what those frames are. The instructor establishes a “stance of curiosity” in which the trainees' mistakes are puzzles to be solved rather than simply erroneous. Finally, the approach includes a conversational technique designed to bring the judgment of the instructor and the frames of the trainee to light. The technique pairs advocacy and inquiry. Advocacy is a type of speech that includes an objective observation about and subjective judgment of the trainees' actions. Inquiry is a genuinely curious question that attempts to illuminate the trainee's frame in relation to the action described in the instructor's advocacy. We find that the approach helps instructors manage the apparent tension between sharing critical, evaluative judgments while maintaining a trusting relationship with trainees.