The supervisor-supervisee relationship is an important relationship between two individuals; a relationship often fraught with conflict and tension. A successful relationship usually culminates in the finished product – the completed thesis; whilst a failed relationship results in the delay of the thesis or the abandonment of the research work altogether. Whilst one is usually trained in the field that one is teaching, lecturers typically become supervisors without any formal training; it is assumed that if one has done research, one can certainly supervise a research enterprise. This reflective paper recounts a senior professor’s evolution as a supervisor of the masters’ and doctoral theses. In this, she asked pertinent questions regarding how she learned to be a supervisor, her actions as a supervisor, her expectations and requirements, and the challenges she faced as a supervisor. She became a supervisor through an apprenticeship of sorts – learning at the feet of her own supervisor. This apprenticeship only shows one side of the equation, the side the student sees, but not the backstage work that comes with it. She discovers that she learns a lot more about supervising thesis through the act of supervising, having conversations with colleagues, reading about the area, and most importantly, reflecting deeply into the enterprise. A conscious, critical, and mindful reflection of one’s actions as a supervisor can help one improve practice and better serve the student whose relationship to a supervisor is very critical to their success.