In this article, Frederick Hess discusses a concept he calls "greenfield schooling." The premise is simple: Profound educational improvement requires more than fine-tuning systems that have evolved over two centuries; it requires policymakers and educational leaders to revisit organizing assumptions about the grammar of schooling. In short, the greenfield approach to school improvement eschews grand solutions in favor of fertilizing the soil so healthy, vibrant reform can shoot up organically. Herein, Hess points out how U.S. schools might have benefited more from this organic, evolutionary approach over grand solutions and big, sweeping actions; discusses how the greenfield approach can be applied to teacher quality; and outlines the opportunities this approach provides for state policymakers to champion creative approaches and fund promising pilots.