Coaching is proposed as a means of improving the learning culture of medicine. By fostering trusting teacher-learner relationships, learners are encouraged to embrace feedback and make the most of failure. This paper posits that a cultural shift is necessary to fully harness the potential of coaching in graduate medical education. We introduce the deliberately developmental organization framework, a conceptual model focusing on three core dimensions: developmental communities, developmental aspirations, and developmental practices. These dimensions broaden the scope of coaching interactions. Implementing this organizational change within graduate medical education might be challenging, yet we argue that embracing deliberately developmental principles can embed coaching into everyday interactions and foster a culture in which discussing failure to maximize learning becomes acceptable. By applying the dimensions of developmental communities, aspirations, and practices, we present a six-principle roadmap towards transforming graduate medical education training programs into deliberately developmental organizations.