Objective: Psychiatric residents’ self-reported confidence levels related to teaching medical students were assessed before and after a five-part teaching seminar series. Methods: Five 1-hour seminars on teaching medical students in the psychiatry clerkship were presented to second postgraduate year (PGY-2) residents. Topics included how to teach psychiatric interviewing, the mental status exam, case formulation, giving feedback, and evaluating student work. Residents were surveyed before and after the seminar series to assess their levels of confidence to teach specific skills. Results: A greater percentage of PGY-2 residents rated themselves as “very confident” in teaching and providing feedback to medical students after the seminar series than before the series. The greatest increases were seen in confidence to teach interviewing skills, the mental status exam, psychiatric formulation, and to evaluate student work. Conclusion: A specific how-to-teach curriculum helped improve PGY-2 resident confidence for teaching medical students during the psychiatry clerkship.