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This research examines flexible working and its impact on retaining experienced teachers, focusing on senior leaders in English primary schools. It stems from a personal experience: after 15 years in teaching and leadership, the researcher left a deputy headship due to inflexible working arrangements. Despite UK legislation supporting flexible work, a disconnect persists between policy and practice. Recruitment-focused strategies have overshadowed retention efforts, contributing to high attrition rates. The Department for Education's 2019 strategy highlighted flexible working as a retention tool, yet its application in leadership roles remains limited. Women, who dominate the teaching workforce, often leave between ages 30-39, partly due to inflexible policies. This study addresses these gaps, seeking to identify enablers and barriers to flexible leadership roles.