Approximately 70% of bridges in Japan are located on municipal roads. Municipalities lack the technical skills of their staff and financial resources, and only 35% of the first round of inspection facilities have been repaired, with only 35% of measures completed. In this situation, municipal officials, as managers, are responsible for being involved in the entire bridge maintenance cycle (inspection-diagnosis-action-record), and therefore, there is an urgent need to improve their technical skills. In this paper, we describe the training of municipal employees to improve their technical skills through on-the-job training of outside workers, using Tamana City Hall as a case study of a local government that faces a shortage of technical skills among its employees. In addition, we show the on-the-job training for internal work that is practiced in the creation of the city’s own bridge summaries for the purpose of improving the level of record keeping. We show that on-the-job training contributes to the improvement of technical skills in the field and motivates city employees by visualizing cost reductions.