In this study, by targeting three railroad companies, we evaluated that on-site management work just as assumed to motivate site workers, and extracted problems in the management. First, we analyzed statement by some field supervisors to grasp a situation of the management and the essential points to activate it. Secondly, we modeled an influence of on-site management on site workers’ motivation. And, we analyzed management effect on site-workers’ motivation by using Hierarchical Liner Models and classified issues on the management of each work site. Thirdly, we suggested safety manager of the Japanese railway enterprises guidelines we made to indicate solutions for the issues. Finally, we verified the effective on activation of on-site management in railway enterprises applying the guidelines to the management. Therefore, the study concludes to suggest the possibility of that the analysis and the guidelines we made contributed to activate on-site management.