This chapter asks the question of what should a teacher of leadership do in a pervasive culture of authenticity when it may be true that a liberal approach to leadership instruction requires the need to create perplexity in students and distance them not only from their society, but from their less talented peers. The chapter compares two alternatives to the teaching leadership in light of the status quo of authenticity: Michel Foucault’s truth-telling and Leo Strauss’s esoteric reading of philosophical texts. Both pedagogies find their root in the Socratic tradition. Foucault emphasizes the process of becoming a subject, a longer and more difficult journey of interior soul searching than is emphasized in today’s university environment. The esoteric method minds the problem of initiating potential philosophers into the search for truth in the context of a precarious social order. Historically, philosophers have faced persecution for questioning conventional pieties. As a result, thinkers throughout the ages resort to subterfuge by concealing their more penetrating insights through esoteric writing, which only a few exceptional minds will be able to understand.