Despite heavy investments in training and development, low-quality education standards and challenges in management practices have been a sticky problem in the Kenyan education sector. Organization Theory guided the main aim of this study in establishing the relationship between management policies and transfer of skills for public secondary school headteachers in schools management. The study adopted a descriptive research design. Questionnaires were used to collect quantitative and qualitative data. Data were analyzed through descriptive and inferential statistics. The study population comprised 226 headteachers.  A mixture of stratified random sampling and census study was adopted in sampling 69 respondents. The results established that management policies explained a 23.4% variation in the transfer of skills for school heads. ?1 = 0.536 and p-value = 0.000 (p<0.05) indicated that management policies had positive and significant effects on transfer of skills. The study established that unsupportive policies like the Students Council, two centers of power, strict policies, and lack of inclusivity in policy formulation adversely affected school heads in implementing learned skills. The study recommends fair representation of all categories of education stakeholders in policies review and formulation to alleviate challenges associated with management policies to enhance the transfer of skills. The Government should address the issue of two centers of power in the public basic education sector. The paper sought to call the attention of the professional development trainers to exercise follow-ups to assess post-training behavioral outcomes in the context of organizational climate.