Exploration of our organisational life has much to gain from fiction so as to reflexively engage with provisional processes of uncertainty, doubt and paradox. These are often neglected qualities of how we go on together in our organizational lives. Taking an autoethnographic approach I present one narrative of a fraught meeting that I was part of to explore my leadership development. I do this in relation to Homer, Shakespeare and Allen-Poe to explore leadership issues of: paradox and how we become enmeshed in unfolding events; the interaction between a leader’s future intent and how this plays out in action. In doing this I offer an invitation to explore literature that speaks to and develops our practice of leadership and how we might develop and communicate useful insights.