From its foundation the literature of classical antiquity exercised a profound influence on psychoanalysis. Today psychoanalytic ideas are considered important not just by psychoanalysts working with individual patients in consulting rooms, but also by students of society and its institutions. However, in the application of psychoanalysis to organizational dynamics, little recourse has been made to ancient authors. In this paper I look at two dialogues by Xenophon and set this alongside a case study from a care-giving organization running psychosocial treatment for people suffering from psychosis. The Xenophon texts present an ethical model of leadership that enriches a more directly psychoanalytic perspective. Taken together, in an integrated way, they can help create a solid organizational pedagogy.