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While studies have shown that mentoring is central to new teacher development (Achinstein & Athanases, 2006), few investigations have examined what mentors learn about themselves as mentors. Via a case study approach, we examined the development of mentoring expertise over a two-year period. Participants were two mentors engaged in a program focused on fostering mentoring expertise. Data sources included transcribed professional conversations, interviews, and reflections. Using these data sources, we found that despite good intentions, mentors’ preconceptions of their role were difficult to change. When evidenced, more substantive change was accompanied by a shift from a focus solely on mentee and student learning to attention to mentor learning as well.