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Mentoring is a complex practice that is distinct from teaching. Effective mentors have a well-developed conceptual knowledge, and the capacity to judiciously enact mentoring practices aimed to support new teacher learning. Currently, there is a paucity of research on how new mentors develop, conceptualize and enact their mentoring practice. This qualitative study seeks to respond to this gap by seeking to understand: What supports/inhibits new coaches’ professional learning and practice? Are there patterns of struggle/challenge that new coaches face? Results indicate that new mentors (referred to as “coaches”) face a range of anticipated and unanticipated intellectual and affective challenges. Coaches also developed insights into the significance of trust and salience of collaboration. Recommendations are provided to support new coaches’ development.