Women across many sectors have often found themselves disadvantaged when it came to assuming different managerial positions, with less opportunities in comparison with their male counterparts. This research aims to explore and investigate how leaders and managers as individuals hold positions of dominance in different business sectors can work under certain circumstances and challenging conditions; from experiencing life under rigid settings, to social peculiarities in the Saudi Arabian context. As such, these overlap with other aspects of social, legal, cultural, traditional, and psychological aspects, uncovering the hidden foundations of resources, procedures, authority, work paths and defects that lead to organisational outcomes and divide between genders. Bourdieu`s theory of symbolic capital and symbolic violence, is adopted in this study which would provide empirical support for this study. The Bourdieusian- notion of symbolic capital and symbolic violence would provide a hypothetical foundation for this study's exposure of the social and cultural dynamics which influences the gender experiences of business leader, both male and female. In addition, a conceptual framework was developed for identifying the various constructs and relationships between them (to be investigated and evaluated) in this study, which included leadership traits, social, cultural, legal, and personal factors. A qualitative interpretivist philosophical approach is adopted for achieving the research aim. Accordingly, semi-structured interviews with 33 participants (including both male and female) leaders in Saudi Arabia are conducted. The initial findings of this research have provided an understanding of Saudi leadership experiences in public and private sector. While government policy such as vision 2030 has been a widely used tool in developing and supporting the role of women in the workplace and positions of leadership, evidence in the research suggests that gender misrepresentation and inequality issues still exist in Saudi Arabia. While gender-specific issues in the workplace were believed to have applied only to women, men have equally had their experiences shaped by similar issues. This study confirms that male/female leaders continue to face several challenges preventing them from achieving equitable representation. Male leaders remain advantaged with access to a higher number of opportunities to help them in their careers, yet they are equally anxious about current competition conversely. The focus of this investigation would not be placed on the gender differences by themselves, but on the ways, these differences can influence organisational performance. This study has both theoretical and practical implications. Firstly, it addressed the gaps in the literature, especially the application of western concept of gender equalities in conservative country of Saudi Arabia, by including the opinions of both male and female genders, and also consideration of social, cultural and legal factors of influence, which led to the interesting findings, reflecting the gendered inequalities greatly affecting women and partially affecting men due to the traditional practices at workplace. Secondly, this study has several practical contributions: presenting a comprehensive view on current practices at workplace in Saudi Arabian organizations reflecting the existence of gendered inequalities. Furthermore, this study formulated policy recommendations as well as recommendations for public and private sector organisations wishing to promote gender equality, making a strong practical contribution.