School leadership and school self-evaluations (SSE) have emerged as central to school improvement and effectiveness. In Irish policy, SSE has had a challenging history as several attempts to embed SSEs have been met by poor clarity around roles of responsibility, a moratorium on middle leadership appointments and more laterally, a global pandemic. However, schools providing for students from socioeconomically disadvantaged backgrounds, known as "DEIS" schools, have proved quite successful in SSEs for over 15 years. This study aimed to explore the leadership and school self-evaluation experiences in "DEIS" schools. This small-scale qualitative study comprised in-depth interviews with school leaders in "DEIS" schools. The themes identified suggest how leaders negotiate a dichotomised societal perspective of "DEIS" schools, and how culture and structure facilitate an empowered collective. The research also highlights SSEs as a space for professionals to also consider their own professional learning in the form of job-crafting.