The United States Census Bureau characterized the position of school superintendent as being the most male-dominated executive position of any profession in the United States (Glass, Bjork, & Brunner, 2001). Paul Houston, president of the American Association of School Administrators (AASA) has stated that the future of school system leadership belongs to women (2004). Research completed in 2005, and updated in 2006, reflected that the representation of women in the superintendency in the state of Iowa is increasingly more discrepant than the national average. In the past two years the percentage of female superintendents in the state of Iowa has continued to decrease. Based on interviews with the three major search firms in the state, interviews with female superintendents and a quantitative statewide survey this paper articulates insights about why this discrepancy may be occurring. These findings could be applicable across the field of K-12 education. The issue extends beyond gender issues to a consideration of justice.