The purpose of this paper is to identify the main problems in assessing reflective learning and to seek ways of tackling them. Lessons are sought from HE’s long engagement with critical thinking that can be transferred to reflective learning. A solution to the problems is offered that is based on a questioning approach to reflective learning. In so doing, the paper explores the nature of reflective learning and advances the idea that the distinction between “surface” and “deep” learning can be generalised to the domain of reflective learning. It concludes with some implications for the development of reflective learning.