A part of diversity management is working to achieve gender equality and create a comfortable working environment for women. However, in many organizations, gender biases and stereotypes frequently occur, consciously or unconsciously, regardless of whether women take on leadership roles. In addition, women must overcome a variety of challenges when taking on leadership roles or aspiring to become leaders. Based on the above background, we review and integrate the literature on management and career studies related to the challenges that women face in the process of advancing to leadership positions in organizations. Specifically, we examine the external and internal factors that create the various obstacles that women who aspire to leadership positions in structured organizations face from a gender perspective. Based on the integrative review, we discuss the implications for practices to increase the number of female leaders.

This study conceptualizes gender inequality in leadership careers as the result of asymmetric forces embedded within organizational environments. The tailwind–headwind framework brings together cultural norms, organizational structures, and psychological responses to explain how the same institutional processes can generate systematically different career trajectories for men and women. By showing how cultural assumptions about leadership become institutionalized through organizational systems and internalized as personal experiences, the framework offers a clear and coherent explanation for the persistent underrepresentation of women in leadership roles.

Women’s advancement into leadership roles remains uneven in many post-socialist labor markets despite high levels of female education and workforce participation. While prior research has emphasized structural barriers and national institutional conditions, less is known about how firm-level organizational environments shape women’s evaluations of leadership as a viable career pathway. This study aims to examine how firm type shapes women’s managerial aspirations across career stages in post-socialist Mongolia. Using cross-sectional survey data from 191 employed women in Ulaanbaatar, aspiration patterns were compared across three organizational contexts: foreign-owned firms, domestic private firms, and public-sector organizations. Career aspirations were operationalized as three states—high aspiration, constrained aspiration, and low aspiration—to capture differences between leadership motivation and perceived feasibility. Pearson’s chi-square tests and Cramér’s V were used to assess associations between firm type, career stage, and aspiration categories. The results show that women in foreign-owned firms are more likely to sustain leadership aspirations, whereas constrained and low aspirations are more prevalent in domestic private firms and the public sector, particularly at mid-career stages. These findings suggest that leadership aspirations reflect organizationally shaped feasibility assessments rather than individual motivation alone, and that firm type operates as a critical meso-level opportunity structure within shared post-socialist institutional conditions.