Wisdom is almost always associated with doing the right thing in the right way under right circumstances in order to achieve the common good. In this paper, however, we propose that wisdom is more associated with deciding between better and worse wrongs; a winless situation we define as tragic. We suggest that addressing the tragic question is something that leaders and managers generally avoid when focusing on business decisions and choices. Yet, raising and confronting the tragic question is important for (...) three main reasons. Firstly, it emphasises that wisdom is about recognising that doing the ethically responsible thing can sometimes lead to acting in ways that violate different ethical norms and values. Secondly, it foregrounds the issue of emotional perception in ethical decision-making. We argue that emotions are salient in directing attention to the tragic question and recognising morally ambiguous situations. Thirdly, the tragic question has important consequences for moral learning, accepting moral culpability for wrongdoing and organisational commitment to righting the wrong. We illustrate our arguments by drawing on three mini-cases: Arjuna’s dilemma in the Mahabharata, Gioia’s deliberations about his role in the Ford Pinto fires and the production of the abortion pill by French company Roussel-Uclaf. (shrink)