Retirement is a process with employees planning decisions generally focusing on the subjective life expectancy, a mental model of years remaining before one dies. Indeed, the real exit of an individual from a career job is accompanied by changes that include social and psychological, resources leading to variations in an individual’s well-being. The purpose of this study was to assess how employees’ engagement in psychosocial programmes affects their retirement preparedness in the education sector in Kenya. The target population was 1,238 teachers aged 50 years and above and employed in public secondary schools by the Teachers Service Commission in Kirinyaga and Murang’a Counties by 2017. A representative sample of 334 respondents was selected using multistage sampling technique. Data was collected using semi structured questionnaire and interview guide. Logit regression was used to establish the relationships between variables in the study and to test the null hypotheses at P ≤ 0.05 confidence level. The findings indicate that even though the sampled pre-retiree teachers were not adequately prepared for retirement psychosocially, yet their engagement in psychosocial programmes increases their retirement preparedness level. The reported findings extend the current understanding of employee separation programmes and raise implications for the various theories that underpin employee separation decisions in HRM.