Objectives: Coaching in medical education has recently gained prominence, but minimal attention has been given to key skills and determining how they work to effectively ensure residents are progressing and developing self-assessment skills. This study examined process-oriented and content-oriented coaching skills used in coaching sessions, with particular attention to how supervisors use them to enhance resident acceptance of feedback to enhance learning. Methods: This qualitative study analysed secondary audiotaped data from 15 supervisors: resident dyads during two feedback sessions, 4 months apart. The R2C2 model was used to engage the resident, build a relationship, explore reactions to feedback, explore resident perceptions of content, and coach for change. Framework analysis was used, including familiarisation with the data, identifying the thematic framework, indexing and charting the data and mapping and interpretation. Results: Process skills included preparation, relationship development, using micro communication skills and techniques to promote reflection and self-assessment by the resident and supervisor flexibility. Content skills related to the specific feedback content included engaging the resident in discussion, ensuring the discussion was collaborative and focused on goal setting, co-developing a Learning Change Plan, ensuring resident commitment and following up on the plan. Together, these skills foster agency in the resident learner. Three overarching themes emerged from the analysis: the interconnectedness of process and content; tensions between encouraging self-direction and ensuring progress and competence; and balancing a coaching dialogue and a teaching monologue. Conclusions: Effective coaching by supervisors requires a combination of specific process and content skills that are chosen depending on the needs of the individual resident. Mastering these skills helps residents engage and develop agency in their own professional development. These outcomes depend on faculty maintaining a balance between coaching and teaching, encouraging resident self-direction and ensuring progression to competence.