Imagination is at the core of entrepreneurship most notably during the process of ideation. Many ideational approaches acknowledge the importance of imagination, but typically ascribe the ability to all individuals as though it does not vary in degree or type. We question this implicit assumption using a creative problem solving lens to identify three different imaginative skills, referred to as creative, social, and practical imaginativeness. Each skill combines the ability of imagination with the knowledge needed to simulate various task-related scenarios used in generating and selecting new venture ideas. After justifying the theoretical existence of these imaginativeness skills, we validate a scale of creative, social, and practical imaginativeness to establish a foundation for empirical testing of the antecedents, consequences, and correlates of imaginativeness. We then examine the efficacy of the three forms of imaginativeness on new venture ideation.