This paper explores organizational and peer dynamics that impact the potential for productive, trusting peer relationships. An in-depth phenomenological study of five peer coaching dyads was undertaken to examine the establishment and maintenance of peer coaching. Joint interviews were used to promote co-construction of responses. Findings suggested that formation of trust is impacted by values-based attachment, confidentiality, and the capacity of peers to make themselves vulnerable. Individual bonds are important at the start of coaching, but trust is further strengthened through contracting and reciprocity within the relationship itself and by an open culture within the organization. Organizational culture was found to influence trust and the need for a combination of benign organizational support, transparency, and non-intervention was seen as vital.