OBJECTIVE As postgraduate medical education increasingly transitions to competency-based models, there is a growing need for faculty to help residents process increasing amounts of assessment data. It has been recommended that a designated resident advisor or coach take on this faculty role, but the literature surrounding coaching in medical education is sparse. The authors evaluated the implementation of different coaching models in a postgraduate psychiatry program to identify drivers and barriers to effective coaching. METHODS The authors conducted semi-structured interviews in September 2019 with focus groups of residents and faculty to understand their experiences of coaching under different models. They identified major themes through a qualitative analysis of the transcribed focus groups, which took place from September to December 2020. RESULTS The authors identified four key themes associated with the implementation of coaching within a competency-based framework, namely role ambiguity, educational alliance, the "idealized coach," and burden. CONCLUSIONS While these findings highlight the barriers that can interfere with effective coaching, particularly in the context of widespread curriculum change, they also illuminate opportunities for the coaching role moving forward. Thus, they offer valuable guidance for present and upcoming competency-based programs as they implement coaching and seek to optimize the learning experience for residents.