We report on a study of how instructors in an online management classroom aim to develop critical reflection through asynchronous discussions. There is an ongoing debate centered on improving asynchronous discussions in online management education but insights into how these discussions could be facilitated to promote critical reflection remains largely under-developed. We address this issue by considering the extent to which management instructors' perception of their role and understanding of being critical impact their facilitation of asynchronous classroom discussions and the challenges associated with this facilitation. Results from 18 semi-structured interviews with instructors teaching in an online MBA program at a UK higher education institution show the potential of asynchronous discussions to promote critical reflection. However, we found that instructors often fail to capitalize on opportunities for critical reflection that arise from classroom diversity and dynamics. Despite the emancipatory intent that underlies program design, interview data reveals three specific areas of interest: the diversity of instructors' interpretations of what constitutes being critical in asynchronous discussions, a range of individualized facilitation strategies and the impact of imposed design constraints. We offer suggestions as to how to improve the facilitation of critical reflection through asynchronous discussions as well as directions for future research.