In the Indian society, one can observe numerous ways in which inequality envisages a figure, gender, class, caste, religion being a few of them. For the purpose of this paper, the researchers would like to delve into the question of gender and analyze it viz-a-viz the current condition of leadership in India. The paper begins by asking important questions as to whether gender matters in becoming a leader in India. The conceptual category of gender is explored through a thorough analysis of how is leadership conceptualized as well as the ways in which rituals, beliefs, and cultural practices essentialise gender roles. The paper aims to chart out the existing gender gap in the corporate sector and offer negotiations to deal with that. Cases of Indian woman leaders are taken up as methodological tools to unpack the gendered dynamics in leadership. The paper attempts to flag the lacunae created in the Indian leadership realm due to sometimes subtle and sometimes not so subtle functioning of patriarchy by unraveling the nuances of working in the corporate sector. Woman empowerment has become a generous subject of concern for our society. Although it is prominently related to social aspect inprevailing scenario it has gained importance in terms of technological and political factors also.