The authors work with practicing teachers learning to become coaches in graduate programs and through professional learning initiatives in multiple school districts. They are also engaged in an ongoing research study of new coach development. Over the last five years, they have observed some common patterns in coaches' learning (Ortmann et. al, 2020). Regardless of their years of teaching experience, school and community contexts, and specific coaching goals, coaches tend to move from scripted, tentative conversations with teachers to more fluid, targeted dialogue about teaching. In this process of growth, the authors have found that new coaches tend to struggle with common challenges. That pattern creates an opportunity to address those challenges proactively and systemically so that coaches can have productive relationships with teachers right away. This article discusses these common challenges and demonstrates how leaders can support coach learning.