Career and technical administrators are faced with a variety of issues and challenges that include, but are not limited to, providing effective ways to help students increase their academic and technical achievement, addressing staff development needs, and integrating CTE with rigorous academic instruction. The emergence of the identified leadership issues was extensive, and the issues command a significant portion of a career and technical administrator's time and resources. This article describes a three-round Delphi approach that identified leadership issues confronting career and technical administrators at the secondary and postsecondary levels in Pennsylvania. The results of the study produced seven major categories and 38 major issues that have implications for career and technical education in Pennsylvania. Career and technical administrators, more than ever before, face increasing leadership issues that have far-reaching implications that will affect their abilities to deliver quality programming for students pursuing entry into the workplace and matriculation to higher education.