Structured dialogue, grounded in self-study, has been used to improve teaching practice, but its effects on mentor practice have not been assessed. This article reports findings from an analysis of the effect of this approach toward teacher development on novice mentor's coaching skills. Using a qualitative inductive thematic analysis using transcripts from audio-recorded mentoring rounds, e-mails, and journals, we found that engaging in structured dialogue enhanced the mentor teachers' ability to ask questions, support novice teacher practice, focus on student learning, and become aware and respond to missed opportunities for coaching and teacher education. These results led us to systematize a holistic approach toward mentorship using mentoring rounds--a form of structured dialogue that explicitly focuses on coaching novice teachers and using self-study to reflect on mentor practice. The strategy used in this study can be utilized for professional development efforts aimed at promoting mentor training.