Community college deans and other senior administrators are faced with a variety of issues and challenges that include, but are not limited to, the ever-changing nature of technology, changes in diverse populations, industry training, and job placements. At this level, the frequently identified emergence of leadership and supervision issues have been more than community college deans can address proactively. Various approaches are used to identify such issues and trends in the field. However, this article describes a 3-round Delphi approach to identifying leadership and supervision issues confronting community college deans over a 5-year period in 4 southeastern states: Florida, Maryland, North Carolina, and Virginia. The results of the study produced 48 major issues and 18 categories that have implications for community colleges throughout the nation. 12 of the 48 issues had a mean score of 4 or more points based on the assigned 5-point Likert-type scale. Community college deans, more than ever before, face increasing leadership and supervisory issues that have far-reaching implications not just for community colleges, but for other 2-year postsecondary educational institutions as well.