External coaches, provided by intermediary organizations, are being utilized to support and develop principals, teachers, and schools and bring about substantive change through communities of practice (CoPs). These coaches provide an external perspective and are integral to the reform process. HRD recognizes the value of coaching in organizational improvement and change, yet understanding the use of external coaches in CoP is lacking in the literature. This article seeks to address this gap by presenting the results from a qualitative case study exploring the roles and experiences of three coaches, in seven elementary–middle schools implementing the Together Initiative (TI) school reform. Researchers' fieldwork consisted of informal site visits and 155 formal interviews with stakeholders involved in the Together Initiative, a reform aimed at improving urban public schools. This study provides a new context for understanding the role of coaching in supporting organizational change.