The purpose of this study was to examine the reasons that deter qualified females who have successfully completed administrative certification programs, from applying or accepting positions in school site administration. Data collection involved semistructured interviews of 12 females who had successfully completed an educational administrative program from 2001-2006. Eight focus areas were selected as a framework for the purpose of data collection. Of these, six were identified from a 1977 study by Stefan Krchniak for purposes of comparison. The eight focus areas explored were: (1) aspiration, (2) assertiveness, (3) personal and situational constraints, (4) discriminatory hiring practices, (5) university assisted job placement, (6) general attitudes and beliefs, (7) role models, and (8) job attractiveness. The study found confidence to be a key factor in participant's decision to apply for a principalship or vice principalship. Administrative role models with similar leadership styles were cited by participants as important in their encouragement to enter school administration. The findings also identified the top desirable and undesirable characteristic traits of school site administration that impacted job attractiveness. Desirable traits were: (1) working with and supporting teachers; (2) developing, planning, and implementing curriculum; (3) leading a school through vision, goals, and accomplishments; (4) supporting and influencing children; and (5) provides new challenges. Undesirable traits were: (1) job too stressful, (2) job requires too much time, (3) held accountable for unrealistic expectations, (4) job holds too many responsibilities, and (5) constant and difficult student discipline. The implications of the study findings are common factors exist that attract or deter qualified female's decision to apply or accept a position in school site administration. This information could be valuable to assist educational administrative certification faculty, field practitioners including school boards, superintendents, and district human resource directors to better recruit and retain women in school site administration.