This conceptual and practical paper aims to expand understanding of imagination in ways that have direct implications for leadership education and research. First, imagination is conceptualized as soil, an analogy that can address misconceptions about imagination and broaden understanding of the multiple ways it contributes to leadership. Next, an educational theory called Imaginative Education (IE) is introduced that offers theoretical understanding of imagination and practical tools for its development. Finally, what imagination "yields" in terms of individual and collective leadership processes is described along with specific "cognitive tools" that may be used to cultivate imagination in school leadership.