Those of us who seek to incorporate imaginative writing into a leadership or organizational context face some very practical - and significant - questions. In this context, the writing must serve a purpose, must have some demonstrable relation to the development of the individual or the organization, or why include it at all? But if one designs writing exercises that have a "point," that address leadership directly, then what they evoke is something less than poetry, with its wild and impractical spirit. This paper proposes that metaphor is the best tool to bridge the worlds of practicality and poetry, to serve the needs of the organization and the demands of art. Specifically, metaphor-based exercises that entail open-endedness, organizational content, and poetic craft can respect the demands of poetry while also serving the needs of an organization.