Clinicians develop as teachers via many activities, from on-the-job training to formal academic programmes. Yet, understanding how clinicians develop the sensibilities of an educator and an appreciation of the complexity of educational environments is challenging. Studies of teacher development have maintained a relatively narrow definition of educational practice. A more expansive view encompasses clinical teachers’ roles in relation to elements beyond learners or content, such as the cultures and other structures of healthcare institutions. In our online Postgraduate Certificate in Clinical Education, space and structure are intentionally created for teachers to think and talk about education with colleagues in other disciplinary contexts. We interviewed 17 students about how their approaches to teaching had changed over a year of part-time study, using their teaching philosophies, written at the start of the programme, as points of contrast. We took an abductive approach to data analysis, drawing on the literature and, unavoidably, our own reflexive interpretations of our practice outside of the research context, such as conversations with students and colleagues; our experiences of teaching and our concurrent research and scholarship. Our themes of repertoire building, perspective shifting, embodied practice, and appreciation of context, describe the increasing complexity of individuals’ considerations of teaching. We use our analysis as the basis for a discussion of the blurring of boundaries between staff and students on such programmes as both groups are engaged in an ongoing continuum of development as all teachers, continue to be learners of educational practice. These insights can inform the ways in which postgraduate programmes can make space for clinical teachers to share and reflect on practices, perspectives and contexts.