The majority of evaluation practitioners begin their career in allied fields and stumble into evaluation. As such, university offerings and evaluation professional development sessions have become increasingly popular. As the field continues to professionalize and new mentoring programs emerge, empirical work examining teaching and training in evaluation has gained traction. However, little is known about the role that opportunities such as mentoring play in evaluation training. The purpose of this article is to explore the expected and unexpected benefits of our experiences as participants in an evaluation mentoring program, lessons learned, and logistical and structural promoters of success in peer mentoring.