The purpose of this instrumental case study was to explore the perspectives of public school principals who began their careers as music teachers. Five principals who formerly worked as music teachers were interviewed about their interactions with music teacher employees, their approaches to professional development, and their music program advocacy. Approaching the topic from the perspectives of musician-administrators was a helpful way to gain insight into common areas of miscommunication between music teachers and principals. Themes included diplomatic relationships, principals' sense of belonging to the music world and sense of readiness for administrative work, and internal advocacy. Implications included the need for increased music program advocacy to other members of the school teaching staff.