Very little is new in project planning, but this is! We present a technique to marry the organization chart with a project's task precedence diagram. This permits us to simulate the project at a micro, project-specific level never before achieved. We can perform “what-if” scenarios related to organization structures, the deployment of specific individuals and skills, and the structure of information flow and exception-handling in a project. The tool used, ViteProject, was developed over the last ten years in a Stanford University laboratory, where substantial results have been achieved when applied to design activities other than software. We present our real-world experience with several software projects, where it has improved project visibility and allowed us to rationally optimize projects in a way hitherto impossible.