Although women are increasingly entering managerial positions, still they remain un-derrepresented in decision-making positions. Within the literature it has been argued that women still face barriers while ascending the leadership ladder. The Glass Ceiling Turned Labyrinth is introduced and elaborated on. A broad discussion on its dimensions, namely Human Capital, Prejudice and Gender Differences, provides a better understanding of the obstacles, which women must overcome throughout their carrier. By navigating the Laby-rinth, women are given possible solutions to overcome the identified inequality within or-ganizations and are encouraged to enter managerial positions.We argue that the stimulation of gender diversity will contribute to economic growth and allow organizations to seize the Gender Dividend. In order to fulfill the purpose of this re-search and provide an answer to the research questions, a qualitative method has been ap-plied. The multiple case study was focused on male dominated organizations from Poland and The Netherlands. The data have been obtained through semi-structured interviews, in which the interview questions were built around four main areas, which were perceptions, expectations, relationships and prejudices of men towards a female manager. An abductive approach allowed us to analyze the insights we gained from the empirical data.Interestingly, some of the research outcomes are in line with previously discussed theory, whereas other parts completely disagree with the literature. From the analysis it can be con-cluded that female leaders in male dominated organizations are not only being appreciated for finding a balance in masculine and femine traits, moreover they are valued for their ob-tained skills, experience and knowledge. None of the interviewees showed explicit objec-tions towards women managers. Through this study, we proved that investing in gender di-versity programs remains to be truly beneficial for organizations and society and can make an impact towards gender equality.