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Workforce retention remains a critical challenge in Head Start programs, with turnover linked to low compensation, heavy workloads, and inconsistent professional development. This study examined alignment between teachers’ and directors’ perceptions of retention-related factors and program-level variation using parallel survey items. Data were collected from 14 Head Start and Early Head Start programs in a Midwest state, including 16 directors and 290 teachers (n = 212 for program-level analyses). Descriptive and inferential analyses showed teachers prioritized classroom-level supports, while directors emphasized structural factors. Wage and workload satisfaction were comparable across groups, but professional development helpfulness varied significantly by programs. Findings highlight areas for improved alignment and inform leadership strategies to strengthen workforce sustainability in early childhood education.