Countertransference, it is widely agreed can either deepen awareness of personal and relational dynamics to the benefit of the work or it can distort and become an impediment through the adoption of defences. The aim of this study was to explore what supported the development of countertransference awareness in an organisational context through a qualitative study. Semi-structured interviews were conducted with 15 therapists either face to face or online. The findings indicate that participants followed one of two pathways, a reflective pathway, where they developed their countertransference awareness to the benefit of the work, and a defensive pathway, the focus of the present paper. Here, the findings suggest that when the organisational setting, the supervisory relationship, and the adopted theoretical framework, did not support the thinking about the relational dynamics, including countertransferential responses, it resulted in the adoption of defences, to the detriment of the work with the client. The implication of the findings, including the limitations of the study and avenues for further research, are also discussed.