The purpose of this qualitative phenomenological research study is to explore why African Americans regardless of their wealth of experiences and qualification, have experienced a difficult time moving up the corporate ladder to positions of authority in most parts of Corporate America. Moreover, this study investigated the effect of transformational leadership to help alleviate the problem, especially in the upper Midwest. The study sought to understand what was in the minds of the African American leaders, as they face issues of workplace restrictions or the so-called “glass ceiling.” The qualitative study also sought to determine how African Americans perceive the potentials of transformational leadership for improving their working situation. Transformational leadership, coaches, inspires, elevate the followers' level of maturity, self-actualization, the well being of others ideals and concerns for achievement. A leadership approach that is defined to creates valuable and positive change in the followers with the intent of developing followers into leaders. The result suggested that the overriding concerns African Americans face in corporate America is centered in fairness, diversity and inclusiveness, inequities, fear, glass ceiling, inferiority complex, and racism experienced by African Americans. Moreover, the study determined that transformational leadership when properly emphasized as a preferred leadership style and implemented could be of help to address the African American leadership concerns.