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The landscape of educational leadership within Thailand's National Education Plan is explored through a qualitative study that delves into the challenges and strategies shaping the career progression of educational leaders. This research, utilizing purposive sampling and semi-structured interviews, examines various facets of educational leadership, particularly emphasizing Human Resource Management (HRM) functions. The findings offer insights that resonate globally, addressing universal issues such as diverse perceptions of career success, dynamics in leadership selection and rotation criteria, and challenges associated with assessment and evaluation processes. While illuminating the promise of the Performance Agreement (PA) system, the study calls for enhanced communication and training.