This qualitative phenomenological study examines the leadership development activities of Illinois community college presidents and sought to understand not only how presidents prepare for their leadership roles, but what challenges presidents are currently facing, what advice they have for emerging leaders about effective leadership practices, and what competencies they identify as important to lead a community college in Illinois today. Utilizing the core competencies defined by the American Association of Community Colleges (AACC) as a framework for the study, the researcher sought to understand the lived experiences of these leaders to help inform a leadership development model for emerging leaders, community college boards, and current community college administrators. Results of the study revealed that a combination of mentorship, progressive job responsibilities, and earning a doctorate were important in the preparation of the participant. Challenges they identified included institutional finances, enrollment management, working with elected boards and unions, and dealing with unfunded legal mandates and legislation. Presidents identified the importance of ongoing professional development, reading and understanding current trends facing community colleges, and building a team as essential leadership practices for community college presidents. The findings from the study align with the AACC's core leadership competencies. Implications and recommendations for practice and future research are included.