This article reflects on an arts-based action inquiry process involving students on an MSc in Management Learning and Change. Following Dewey’s (1934/2005) contention that art is grounded in experience, we adopt a purposefully non-aggrandising perspective on ‘leadership as art’, arguing that this prompts greater critical attention to possibilities for inclusiveness in these realms of human endeavour. We propose the present inquiry, in which participants were invited to create leadership touchstones, or dolls, as a way of learning about leadership and themselves as leaders. Drawing from therapeutic and psychoanalytic perspectives, we explore dolls’ power to provoke, unsettle and evoke strong reactions on the part of their makers, and demonstrate how these dynamics played out in our inquiry. We highlight the conditions which enabled participants to engage with the tensions and ambiguities raised in ways which held open possibilities for reflexivity. We conclude that leadership, like art, can most constructively engage with the human condition when it is able to hold, not collapse, our experience of the uncanny, the abject, and the other—including the ‘other’ within the ‘self’—within the complexities of organisational life.