How leaders and managers respond to not knowing is highly relevant given the complex, ambiguous, and chaotic business environment of the twenty-first century. Drawing on the literature from a variety of disciplines, the paper explores the dominant, unfavorable conceptualization of not knowing. The authors present some potential ethical implications of a negative view of not knowing and suggest how organizations would benefit from identifying any unhelpful aspects of the culture that may encourage unethical, undesirable, and/or hasty actions in situations of not knowing. The paper specifically illustrates how patience, courage, honesty, integrity, and humility are integral to negative capability in the contexts of not knowing. Finally, the paper calls for deeper inquiry into the role of virtue ethics in preparing managers and leaders for not knowing and urges organizations to embrace negative capability in not knowing rather than engaging in damaging delusion.