This study explores coaching during transition from medical school to residency through the perspectives of residents and faculty coaches participating in a coaching program from residency match through the first year of residency. From January to September 2020, 15 faculty coaches in internal medicine, obstetrics and gynecology, emergency medicine, orthopedics, and pathology participated in a synchronous, in-person coaching training course. All 94 postgraduate year 1 residents in these 5 training programs participated. Between November 2021 and March 2022, focus groups were held with interns from all residency programs participating in the program. Interviews were conducted with faculty coaches in February 2022. Faculty and residents discussed their experiences with and perceptions of coaching. De-identified transcripts were coded, and researchers organized these codes into broader categories, generated cross-cutting themes from the concepts described in both cohorts, and proposed a model for the potential of coaching to support the transition to residency. Descriptive themes were constructed and analytic themes developed by identifying concepts that crossed the data sets. Seven focus groups were held with 39 residents (42%). Residents discussed the goals of a coaching program, coach attributes, program factors, resident attributes, and the role of the coach. Coaches focused on productivity of coaching, coaching skills and approach, professional development, and scaffolding the coaching experience. Three analytic themes were created: (1) coaching as creating an explicit curriculum for growth through the transition to residency, (2) factors contributing to successful coaching, and (3) ways in which these factors confront graduate medical education norms. Learner and faculty perspectives on coaching through the transition to residency reveal the potential for coaching to make an explicit and modifiable curriculum for professional growth and development. Creating structures for coaching in graduate medical education may allow for individualized professional development, improved mindset, self-awareness, and self-directed learning.