Much like a Jazz group, successful middle level schools are also founded on elements of improvisation, collaboration, teamwork, and responsive communication. Just as the director of the jazz group must have a solid foundation of music theory, the skills to bring out the best in the players, and an attitude that allows others to shine, those who choose to lead middle level schools must also possess the knowledge, skills, and attitudes to help their staff members and students teach and learn passionately. This article employs the analogy of a Jazz ensemble to illustrate the concept of the many things required of an effective middle school principal. It also considers that middle school leadership is not for the faint hearted. Kinney and Tomlin, both middle school leaders themselves, speak from their own experiences when they say that leaders are often called upon to show courage, determination, and persistence to lead a successful middle level school. Here the authors suggest that knowing what you know, and what you don't know, and being open to having others help fill in the gaps, can be important building blocks for middle school principals' successful leadership.