This article examines the learning by a dean of education through the process of executive coaching. In adopting a self-study approach to explore the experience of executive coaching, we draw on the notion of critical friendship as a way of interrogating the experience and the response to that experience in terms of leadership development and professional growth. We used data from audio-recordings of individual coaching sessions to construct vignettes designed to capture the essence of particular themes and issues germane to the learning through the coaching experiences. The major findings pertain to the notion of default behaviours and show how recognition of one's own default behaviours is important in shifting personal practice. The study opens up for scrutiny important aspects of the nature of the personal side of leading a faculty of education and offers insights into what it means to be a learner as a leader and how productive self-study can be in facilitating that learning process.