This study examines insights from Career and Technical Education (CTE) leaders that help to better inform the preparation of all school leaders. CTE leaders find themselves in the interesting position of being inside the PK-12 system but at the outside edge. This outsider within perspective not only gives CTE leaders a unique understanding of schools but also on the preparation of school leaders. These practitioners helped to identify three key areas of focus for leadership preparation: a new focus on college and career readiness, the importance of instructional leadership, and an expanded understanding of community.