Research in educational program administration provides insights into the operationalization of programs or organizational services; however, an area of research that is long due exploration and development is how English language programs (ELPs) differ in terms of planning, organization and services and the job English language program administrators (ELPAs) perform in their roles. This paper reports on collaborative autoethnographies of three ELPAs who share their experiences of encountering administrative challenges and devising effective strategies to address them. Employing a qualitative research design, data were collected through critical self-reflections, individual research discussion dialogs, notes sharing and a focus group. While we confirm that administrative challenges exist in ELP administration, the findings of this study add that the nature and extent of these problems (e.g. cultural diversity, course alignment, power relations, racism, recruitment) can be different from program to program and context to context. The main finding of this study is that successful ELP administration requires a good understanding of the macro-culture (e.g. national context, university culture, administration at large) as well as the micro-culture (e.g. program level policies and practices). This study has significant implications for leadership training in ELP administration and future research projects investigating context-specific leadership in English education.