While many studies have analyzed educational hiring practices through the lenses of recruitment, retention, and promotions, this qualitative dissertation study examined the experiences that Black educators endure in their journeys into leadership positions. Qualitative interviews allowed Black educators to speak their truths on policies, processes, and preparation for leadership and shed light on institutional and systemic barriers that discourage pursuit of advancement. Study participants were five Black women (an assistant principal, an athletic director, a data analyst, and two teachers) and three Black men (an assistant principal, a teacher, and a behavioral support teacher). The eight participants detailed their perspectives on leadership preparation, their roles and responsibilities, preparation for a leadership interview, the interview process, promotion of colleagues of other racial groups, and their perspectives on how their journeys differ from those of aspirants of other races. Despite attempts to achieve diversity, racial and gender demographics in education leadership are disproportionate in terms of Black educators. This study examined how the journeys of Black middle school educators have shaped their perspectives on hiring practices, how others assess their worth, and how Black educators view the work of other ethnic groups. [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.]