Residents are essential teachers of students and interns, yet few opportunities exist for them to improve their teaching skills. The authors designed and implemented a longitudinal teaching skills curriculum for second-year categorical medicine residents on ambulatory block. This curriculum involves residents giving talks to one another, with close observation and personalized guidance by faculty in one-on-one and group feedback sessions. Evaluation by self-assessment surveys administered at the beginning and end of the curriculum showed significant improvement in nearly all of the domains assessed, including overall teaching skills. Intensive interventions can improve resident teaching proficiency and thereby improve the education provided to trainees.