The purpose of this study is to clarify what factors affect both the intentions and obstructions experienced for university staff members considering going to graduate school. In recent years with the advancement and specialization of jobs at higher education institutions, several graduate courses for university staff have been established. However, while some staff go to graduate school, the majority do not. This paper aim to explore the causes for this difference. A secondary analysis using the data from the “National University Administrative Staff Survey” was performed. The study found significant differences among several factors (age, presence / absence of knowledge to be learned, intention to take other learning opportunities, fields of interest, etc.) between those who had the intention to go to graduate school and those who did not. Similarly, there were significant differences among several factors that related to the work environment between those who felt obstructed to go to graduate school and those who did not. An analysis was performed to discern whether the intention of going to graduate school had relation with individual’s perceived obstructive factors, yet no significant difference was related to individual intention. These results suggest the necessity to explore various measures more thoroughly such as methods to promote learning from an early stage, to communicate with employees to give them clear indication for career path, and to improve the work environment.