While executive coaching has been mostly portrayed as a straightforward practice, relying on a relatively non-problematic set of relationships, our research highlights the multi-faceted nature of this intervention in organizations. To do so, we conducted 20 semi-structured interviews, using a critical incident technique to explore situations where coaches faced different or conflicting agendas and interests between the coachee and the organization, within a triangular coaching contract. We adopted a qualitative research method, and a grounded theory research design, using an abductive reasoning. This study highlights the multiple stakeholders involved in a three party coaching relationship, as well as the different roles they play and interactions that exist among them. It also offers a careful analysis of some of the agendas in executive coaching, and their different characteristics. Additionally, by studying the challenges faced by the coach, our research offers an in-depth look at the identity issues and contractual complexities related to power dynamics and office politics in coaching.