A growing body of literature examines the impact of impostorism on people in organizations. Most studies assume that one must reduce impostorism to succeed as a leader, however we contend that the experience may facilitate development, if approached with a paradox mindset. Drawing on paradox theory, we introduce a novel concept, the leader impostorism paradox mindset, and present a conceptual model of its development. We posit that leader impostorism is an inherently paradoxical experience as leaders hold two contradictory cognitions (1) ‘I believe I am less capable as a leader’ and (2) that ‘others believe I am more capable as a leader’. Leveraging paradox theory and the notion of ‘working through paradox’ we suggest that thinking about both contradictory conditions is helpful for one’s development as a leader. We propose three learning mechanisms to develop such a mindset: Self-reflection, vicarious learning, and play. We present the ‘Two Islands’ exercise as one illustration of how to facilitate the development of a leader impostorism paradox mindset. By giving an example from an MBA class, we provide insights into participants’ learning experiences. We conclude by discussing the practical implications of developing a leader impostorism paradox mindset, and by mapping directions for future research.