This paper reports on a case study of aspiring Canadian school leaders participating in a postgraduate online course in which the instructional approach was grounded in critical social theory. The focus was on using dialogue, questioning and critique as a means of uncovering assumptions, values and tensions as participants related their lived experiences as learners to those of students in their own educational settings. Initially, the critical approach induced feelings of vulnerability and "not measuring up". Final outcomes were participants' deeper understanding of how they learned, how their assumptions about education impacted their actions, and how their actions impacted their own students.