Residents-as-teachers (RaT) programs are believed to offer benefits in enabling residents to become more effective teachers. However, these programs are quite resource-intensive; therefore, it is critical to understand the effectiveness of these programs. Evaluating RaT programs is challenging and requires special consideration because residents play dual roles as clinical teachers and trainees. The program evaluation is a trade-off between the participation of busy residents and the reliability of the data. In addition, the beneficial effects on residents themselves as well as their institutions are typically not considered in effectiveness evaluations. In this article, we share our experience in evaluating our RaT program by utilizing Kirkpatrick's hierarchy and offer lessons learned and strategies for success. We suggest that leaders of these programs build a robust evaluation plan prior to delivering the instructions to confidently validate the effectiveness of RaT programs.