The current study is an assessment of challenges of strategy implementation social
security institutions a case study of National Social Security Fund. The study adopted a descriptive case study research design. The population of the study was 1660 employees of NSSF. Sampling targeted 10.4 percent of the total population of employees. Stratified random sampling was used to select the 173 employees from three strata namely, top management, middle management and junior officers. The study adopted a descriptive case study research design. Data was analyzed by the use of descriptive statistics and inferential analysis. Specifically, means, frequencies and percentages were used. Factor Analysis and Correlation analysis was used to extract the relevant factors and their relationship with strategy implementation. The findings presented in tables, figures and graphs. Findings indicated that the organization leadership at NSSF is not effective and this may have led to poor strategy implementation. The culture at NSSF was not conducive for strategy implementation and this may have led to poor strategy implementation. The organization structure at NSSF was inconsistent with strategy implementation and this may have led to poor strategy implementation. The management of organization resources at NSSF is not effective and this may have led to poor strategy implementation. The organization politics at NSSF are not conducive for strategy implementation and this may have contributed to the poor implementation of strategy.