COVID-19 has accelerated the spread of telecommuting in Japan. In past studies regarding telecommuting, it was proved to be the result of i-deals, so it was discussed in the context of location flexibility i-deals (LFi-deals). The spread of COVID-19, however, has given rise to semi-compulsory telecommuting. Therefore, this study takes three groups: Group A, which continues to work at the office as before; Group B, which has started to telecommute (inexperienced telecommuters) so that telecommuting is regarded as semi-compulsory; and Group C, which has experience with telecommuting (experienced telecommuters) so that telecommuting is the result of making LFi-deals; and investigates the relationship that telecommuting has with the degree of self-determination (DSD) and productivity. Our analysis found that between Group B and Group C, which were both telecommuting, both DSD and productivity were significantly higher for Group C which has LFi-deals compared with Group B, for which telecommuting is semi-compulsory. However, DSD and productivity were higher for Group B than for Group A, so it is possible that starting to telecommute leads to more LFi-deals, a greater DSD, and higher productivity.