Despite the remarkable increase in the existence of women in the workforce, the entry of women into higher managerial positions remains restricted. Various studies have confirmed this fact. This phenomenon of hampering women’s upward advancement to senior management positions has been referred to as the glass ceiling effect (GCE). It is therefore recommended that organizations (both private & public) embark on enlightenment campaign and also incorporate equal opportunity of employment in their company or organizational policies. The findings reveal that the Glass Ceiling and Women Career Development (WCD) have a moderate negative relationship and also show that Individual factors, Organizational factors and Cultural factors have a significant effect on Women Career Development. The present paper analyses the gender gaps and discrimination of women in their career. The major impediments affecting women’s participation in the workforce is the lack of education and skills. It also focuses on the significant effects of the Glass Ceiling on Women Career Development (WCD) of Executive level and small scale business level. The Twelfth Plan envisages a major scaling up of skill development for women from traditional skills to emerging technical digital skills, which help women break the gender stereotypes and move into employment requiring higher skill sets.