Current research reveals a large percentage of teaching positions and administrative services credentials are held by women, although historically, men dominate the superintendent role. Specifically in the area of women in the superintendency, a discrepancy exists between men and women in recruitment practices, types of barriers and challenges, and the length of time one stays in the superintendent position. This study examines the superintendent role and the perceived leadership qualities necessary, barriers, challenges and opportunities, as well as the career pathway taken by those in the superintendent role. With a mixed-method design, the study reflects upon responses from six superintendents, three women and three men, using semi-structured interview questions and data collected with Bolman and Deal's (1990) Leadership Orientations (Self) Instrument and a demographics survey. A theoretical framework of management and leadership styles was utilized to analyze the data for themes relating to the three research questions. The findings generally indicated women superintendents perceive they are expected to act and behave differently to succeed in the role, while men are more at ease with making decisions and leading others. Gender biases were found to be prevalent for women, as the role of parenthood was the biggest barrier when considering their career pathway. This was not found to be a barrier for men.