The aim of this study is ‘to explore the barriers that impede career development of Sri Lankan women managers in public and private sectors’. In this study, an interpretivist philosophy as the researchers view and the respondents view has adopted. Qualitative case study methodology with feminist-oriented research method was used to answer the questions. By this study, it has been analyzed the experiences of 40 Sri Lankan women who are holding senior-level management positions in five public and five private sector organizations. The grounded theory analysis method was applied to analyze the data. The findings confirmed that women remain under-represented in top management positions. Organizational culture, situational and personal factors have affected these situation. However, the study confirmed that the Organizational cultural, situational and personal factorsare not affecting managerial effectiveness of the women managers. Generally, they do not show dialectical behavior in their managerial positions and use their style in a non-traditional manner. There is still a need to push for equal representation of women in top management positions in both sectors.