In spite of the research highlighting the significance of the presence of Black administrators to the success of Black students, there continue to be noticeable disparities in the representation of Black and White administrators in higher education. The racial and ethnic makeup of institutions of higher education does not reflect the demographics of the U.S. population. Black administrators are disproportionately underrepresented throughout academe, and are even more sparse at the executive levels of leadership. The purpose of this study was to examine the perceptions and attitudes of mid-level Black administrators with respect to progressing into executive-level administrative positions at predominantly White institutions. Relevant scholarly literature on mid-level administrators, career advancement, and racial barriers in higher education were examined. Three major tenets of Critical Race Theory (CRT) in education were used as a theoretical lens to examine racial inequities and disparities Black administrators experience in the academy. To address the research question and to explore the subjective viewpoints of the participants, Q methodology was utilized. After IRB approval, purposive sampling was used to recruit 40 Black mid-level administrators to participate in the study. All participants held one of the following titles: Director, Associate Director, Assistant Director, Dean, Associate Dean, Assistant Dean, and Manager. They each worked for a bachelor's degree granting public college or university. In addition to their title, the participants had to have earned at minimum a master's degree. Semi-structured interviews were held with 8 of the 40 participants. Content from interviews, questionnaires, and literature contributed to concourse development. By removing redundant and useless items, the concourse was refined and condensed from 90 statements to develop a Q sample of 41 statements. Through an online process, 40 participants sorted the 41 item Q sample that represented the full gamut of perspectives regarding the subject of career progression in higher education. In the sorting process, the participants ranked the statements based on their personal views and beliefs. A review and analysis of data resulted in five factors that categorize and represent the subjective viewpoints of the participants. The factor arrays, post-sort comments, distinguishing statements, and demographic details aided in interpreting and naming each factor. The five factors were named: Factor 1: The Disconnected, Factor 2: The Disadvantaged, Factor 3: The Disrespected, Factor 4: The Dismissed, and Factor 5: The Disinterested. Each factor was analyzed and interpreted to provide descriptions of how Black administrators perceive career progressions in higher education. Recommendations to expand the study were included.