The objectives of this study was to suggest countermeasures against problems of teacher management systems due to the conditional changes in vocational high schools. Various research methods were used in order to accomplish this study. Extensive literature, statistical data, and related legal regulations were collated and reviewed. A panel of expert committee, which consisted of officials in the Ministry of Education and the Provincial Offices of Education, vocational high school teachers, professors, and researchers, was held several times in order to discuss and search the future directions of management systems of vocational high school teachers. Survey with the questionnaires were conducted, which subjects were members in the 16 Provincial Offices of Education, the principals, and teachers in the vocational high schools. The results of this study indicated that the countermeasures, which make the current teacher management systems flexible and actual, should be developed for coping with the challenges in vocational high schools and for improving the management systems. In addition, based upon that countermeasures against teacher problems are sensitive issues, it is essential for enough discussions, examinations, and social agreements on the policy measures as the management system. Based upon the results of this study, the researchers make some recommendations for policy execution and further research.