This study brings forward a narrative inquiry into the barriers faced by women principals in a typical Pashtun society. A total of ten women principals were selected for interview. It was found that every woman in Pashtun society is more focused on her familial affairs than her professional career. This diversion of women is caused by the prevailing role expectations which every woman wants to associate with. Role expectation is one of the primary and stronger barriers that restrain women from developing their leadership careers. Leadership barriers are in abundance, however, role expectation has a strong psychological impact on women. Women who work outside their houses in different organizations are divided into familial and professional spheres. A woman is the manager of the familial affairs and she remains entangled in house chores more than in professional affairs. Focusing more on familial affairs is preferable to professional career development. Living in a culturally sensitive social setup in itself is a barrier to developing professional career or skills. Every culturally sensitive society is divided on different ethnic, racial and gender lines which become harder for those people on whom these sensitive lines are drawn. Similarly, the Pashtun society is divided on different ethnic, racial and gender lines that restrain women from certain activities that are sensitive for them. The social environment in Pashtun society is based on certain stereotypical practices that hinder women in their leadership skills and career development.