This paper attempts to relate the critical analysis of religious or “sacred” metaphors in leadership to the theory of askēsis, the idea of leader as an incarnation of a virtue defined as “the formation of a full, perfect, complete and self-sufficient relationship with oneself.” A model of leadership based on askēsis, it is argued, is established by means of the form of rhetoric called the exemplum, by means of which leaders derive authority from their being held to be a living (or dead) incarnation of an ideal of perfection, and their life being narrated as a “perfectionist vita.” The principal means of communication of this exemplarity is the hagiography, which finds its contemporary equivalent in the popular CEO (auto-) biography, which can be interpreted as a reactivation of ancient hagiographic archetypes. In readings of three leader hagiographies, focusing on the narrative, rhetorical, and discursive strategies employed, it is shown how the dubious moral exemplarity of such individuals is established. The paper concludes with a discussion of the differences and analogies between the medieval hagiography and the contemporary CEO (auto-) biography, and a discussion of the relationship between asceticism and charisma in the light of these examples.