This paper critically examines the social work profession in Canada and the gender representation in managerial roles across the country. Reviewing professional literature on gender representation in the workplace, specifically in managerial or supervisory positions of power. By critically exploring the unequal distribution of power to male presenting individuals in a mostly female-dominated profession, we challenge the dominant paradigm of male power and privilege in social work. Recommendations are made to create better gender diversity and representation in power positions in a profession that seeks to empower others and break down gender stereotypes in front-line work. A theoretical perspective was undertaken navigating sexism, internal segregation, and collective bias/ stereotypes. Although social work applies anti-oppressive practice, the imbalance of policy versus expectation and practice versus reality is stark.