To help address enrollment and financial challenges institutions of higher learning may benefit by having a better understanding of entrepreneurial leadership orientations, or skills, of academic deans. This study revealed several significant correlations between the self-reported entrepreneurial orientations of academic deans in upstate New York, working in independent colleges and universities, and certain demographic characteristics of their positions. Academic deans reported "team builder" and "proactive" as their two highest ranked, self-reported entrepreneurial characteristics, while "risk taking" was ranked as the lowest characteristic. The results indicated a significant correlation between certain variables applicable to academic deans' positions, such as years of experience and job expectations, with the self-reported entrepreneurial orientations of such deans.