There is very little research on imagination in the context of leadership in general, and even less in relation to educational leadership. Drawing on available research on imagination in leadership and scholarship in the field of imagination, this qualitative content analysis seeks to add to foundational understanding of imagination's role in educational leadership. First, it describes the range of meanings leaders hold about imagination and the contradictory feelings these meanings create. Second, it indicates some of the varied ways in which imagination contributes to leadership. Third, it contributes a definition of imagination that encompasses the potential value of imagination for leadership now and into the future. The paper concludes by offering recommendations for future research and identifies the "improvisational" imagination as an additional feature that imagination contributes to leadership practices. The research shows that imagination is not something we should call on only in times of crisis, but, rather, that it is an indispensable ally in dealing with leadership challenges of all kinds.