This study explored the multifaceted journey of Black women ascending to senior-level leadership positions within Illinois community colleges. It aimed to uncover, understand, and provide actionable recommendations concerning the progression of these women into prominent roles, focusing on their unique identities, the impact of leadership support, and the necessary strategies and support for their advancement. Through in-depth narratives in a basic qualitative study with 12 Black women in senior administrative roles, the research garnered their paths to leadership, the barriers and biases encountered, and the means of overcoming these challenges; to understand the nuanced experiences and the complex interplay of race, gender, and leadership within the academic sphere. The research revealed critical themes, including how they navigated barriers to their leadership pursuits, expressions of resilience, and the importance of mentorship and professional development. The research found that while Black women face a representation deficit, stereotypes, and microaggressions; they exhibit resilient leadership and a reliance on holistic self-development strategies. Institutional leadership is pivotal, with systemic challenges and opportunities significantly impacting their progression. The study emphasizes the need for robust support systems, institutional backing, and advocacy to facilitate their ascent into leadership roles. Moreover, the study provides in-depth research on the intersecting challenges of race and gender in leadership, advocates for a more inclusive approach in higher education leadership and serves as a guide for institutions to foster a fair and supportive environment for Black female leaders. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]