© 2014, © The Author(s) 2014. This article explores how storytelling and Greek mythology within classroom-based leadership development may facilitate learning to deal with ambiguity and social construction in leadership practice. We aim to show how using narratives and making explicit tacit plotlines can disrupt thinking and enable participants to experience the emergent process of re-storying. We argue that the projective focus of the re-storying process encourages critical self-reflection and discussion of the socially constructed nature of organisational roles, relationships and leadership. The use of Greek mythology archetypes in combination with re-storying helps participants to question taken-for-granted assumptions of leadership practice, explore emotions and reflect on the past, present and future of a story. Drawing on reflections from practice, we propose a re-storying leadership development workshop and highlight complexities of working within the realm of re-storying and critical self-reflection. This article concludes with an outline of avenues for future research and leadership development practice.