This research is intended to explore the limited study of leadership development across three areas of educational leaders: K-12, higher education professional (HE-P) (not in academics), and higher education academic leaders (HE-A). Background: Educational leaders from these three different groups are often viewed and treated separately, both in areas of research and practice. Methodology: A brief electronic survey was sent to over 600 educational leaders equally distributed across these three areas. Findings: There was noteworthy congruence in terms of the leadership theories utilized across the groupings, but differences in terms of where they received much of their professional education regarding leadership. Future Research: This study raises questions regarding efficacy of professional development approaches, the value of leadership development per se, and the potential value of bringing together the three groups in professional development activities as a means of forging a more seamless system for students.