This article brings attention to a seemingly pervasive and underlying assumption in critical management education that transformative learning is a good thing. We explore this assumption through a series of narratives examining the ethics of educators overtly seeking to enable transformative learning with owner-managers in order to impact on their businesses. The focus on owner-managers is of significance in terms of transformative learning because of the centrality of the owner-manager to the delicate ecosystem that is the small and medium business. The article makes salient relational care in critical management education and the need for educators to engage in a moral dialogue regarding the relational impact of transformative learning in pedagogic designs. Such dialogue necessitates addressing in whose interest is transformative learning being sought, along with the orientation and framing of such learning.