The anticipated increase in chief executive officer retirements along with an identified shortage of qualified candidates to fill these vacancies has created a high level of concern throughout the community college system. To address this situation, the American Association of Community Colleges (AACC) board of directors approved the "Competencies for Community College Leaders," specifying a set of six competencies to be used as a framework for community college leadership development (AACC, 2005). Although 100 percent of the respondents for the initial review of the list rated each of the six competencies as "very" or "extremely" essential to effectively performing in the various roles expected of community college leaders, responses to questions about how well their formal training prepared them to meet these competencies was not encouraging. Further, Amey (2005) suggested that it remains unclear whether any of the graduate school leadership development models sufficiently provide what the next generation of community college leaders actually needs to learn. A better understanding of how presidents learn the skills and develop the traits and competencies necessary to be successful transformational leaders is needed to help resolve the leadership crisis as talented pools of potential candidates are identified. Data findings from the "Community College Presidency Demographics and Leadership Preparation Survey" (Iowa State University) addressed leadership preparation, career pathways, and perceptions about the AACC competencies (Duree, 2007; McNair, Duree, and Ebbers, 2011). This chapter reviews what competencies need more personal development to master and what competencies receive less prominence in practice.