Explored in the qualitative phenomenological study were the potential executive leadership capabilities and attributes for a new fourth generation of emergent female leaders in the 21st century and the organizational and cultural obstacles female executives faced in upward mobility. Sixteen female community college vice presidents in New York State participated in the qualitative investigation. Five major themes emerged from the study related to leadership development and accession strategies within community colleges: (a) preparing for the presidency, (b) leadership trends for the 21st century, (c) a split on perceptions of gender effects, (d) lack of interest in pursuing the presidency, and (e) perceived obstacles affecting female accession. As community college leaders prepare to fill an impending leadership gap predicted for the 21st century (Weisman & Vaughan, 2007), findings from the study may provide insight into understanding the requisite leadership skills, contexts, and obstacles that challenge female executive leaders in accession to higher-level positions within community colleges.