Teacher development, whether in pre-service teacher education or in in-service coaching, is a complex and context-dependent enterprise. As schools recognise the need to provide embedded and extended professional learning opportunities for novice and veteran teachers, the role of coaches has expanded. This study explores how coaching differs depending on the role of the feedback-giver, as well as what holds consistent across roles. The context is a large urban middle school in which the same coach supported teacher development in the area of English as a second language instruction through varied roles. Following Meyer-Mork (2010), we employed self-study as a methodology uniquely suited to offer insights into the interactions that took place in coaching conversations carried out by Marcus (Author 1). Laura (Author 2), supported Marcus by serving as a critical friend and offering commentary on the self-study in an effort to examine Marcus’s coaching from different perspectives. We were able to reflect on the various ways these roles are designed to support novice teachers. Our findings indicate that the role of the coach subtly shifts based on the relationship with the teacher being coached, and more understanding is needed within the coaching literature to better parse the overlaps and differences based on role relationships.