This qualitative study explores the perceptions of senior-level community college administrators regarding the community college presidency and the challenges that may deter qualified candidates from pursuing the role. While existing literature has examined the preparation, qualifications, and recruitment of community college presidents, as well as the difficulties they face, there is a gap in understanding why experienced administrators choose not to pursue the presidency despite being well-qualified. This study seeks to address that gap by investigating the factors that influence the career decisions of potential candidates. The community college presidency has long been viewed as the pinnacle of a higher education career. However, in recent years, the role has become increasingly burdened with both internal and external challenges. Internal challenges include issues related to student enrollment, retention, faculty relations, accreditation, and technology, while external pressures encompass legislative concerns, fundraising, and diminishing public confidence in higher education. Moreover, the increasing complexity of the role, coupled with the erosion of work- life balance and personal privacy has led many senior administrators to reconsider the presidency as a viable career option. This research study aims to understand both the perceived challenges faced by community college presidents and the reasons why senior-level administrators opt out of the presidency. By examining the perceptions of twelve senior administrators from two midwestern states, the study seeks to provide insights into the growing leadership gap within the community college sector. The study is guided by two research questions: (1) What challenges facing community college presidents do senior-level administrators consider when deciding whether to pursue the presidency? (2) What challenges are the most prevalent reasons preventing senior administrators from pursuing the presidency? The research uses qualitative methods, including online surveys and virtual interviews, to gather data. Findings from this study will offer valuable insights into the factors influencing leadership decisions in the community college sector, with implications for leadership development, succession planning, and addressing the growing leadership gap in these institutions. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]