Objective: The training objectives for postgraduate education in the United States and Canada both state that teaching skills should be formally developed during training. This article reviews the development of the Teaching-to-Teach program at the University of Toronto Department of Psychiatry, the current curriculum, evaluation, and future directions of the program. The authors highlight some of the challenges encountered and discuss ideas for implementation of similar programs in diverse training settings. Methods: A Teaching-to-Teach curriculum was developed with separate tracks for junior and senior residents. Topics covered include one-to-one teaching, the one-minute clinical preceptor model, challenging teaching scenarios, and providing effective feedback. Results: In 2007, 100% of residents who responded to an evaluation questionnaire agreed or strongly agreed that the topics covered were relevant, and in 2008, 92% of respondents agreed that topics were relevant. In 2007, all respondents agreed or strongly agreed that they felt more prepared to teach. In 2008, 85% of respondents felt more prepared to teach. In 2007, all respondents felt that the amount of teaching was good or too little, but in 2008, 46% of respondents felt there was too much teaching. Conclusion: The large size of the University of Toronto psychiatry program may make this curriculum difficult to generalize to smaller training sites. The use of online modules, collaboration between programs, or individual teaching electives may be other ways of implementing a teaching to teach program. Overall, our curriculum was well-received by trainees and they felt better prepared to take on the role of teacher after participating.