This thesis argues that a systems and design thinking approach to education can have a transformational affect on individuals and organizations. This thesis looks at the Curtis Institute of Music and how the school is challenging students to expand their thinking by involving a diverse group of stakeholders in the complete redesign of performance experience. A description of an interactive planning and idealized design project, called the Curtis Leadership Workshop, is presented. This thesis specifically provides an overview of the theory, model and applied methodology, and an account of the preparation for and first critical steps of the project. Outcomes of critical steps are presented and a number of research questions for a formal impact analysis are proposed.