This study examines two female principals in upper secondary schools and the development of their professional identities, focusing on schools in Sweden and Texas, USA. The study is part of a larger international research project with global conversations about what successful leadership means, and asks: in what ways do female secondary school principals' professional identities inform equity issues in leadership with implications for recruitment, hiring, and evaluation practices? Using a feminist post-structural discourse analysis, the findings revealed that even when successful, female leaders in upper secondary schools can be evaluated negatively. These considerations relate to the way in which female principals are recruited, hired, and weighed when appraised, where their contributions may not be fully incorporated to establish equitable processes and procedures to sustain their success in educational leadership.