The purpose of this study is to examine the factors that promote learning in middle managers through their experiences of developing new business. A questionnaire survey was undertaken on 371 subjects who had experience of being part of new-business departments as middle managers in private enterprises with over 300 employees. The analysis results revealed the following. First, an individual factor that promotes learning through new business development experience is learning goal orientation. Second, the organizational factors that promote learning through new business development experience are management support and work discretion. Third, a workplace factor that promotes learning through new business development experience is introspective support from one's superiors. Fourth, it was found that the factors management support, work discretion, and introspective support would act as intermediaries for the individual factor learning goal orientation, triggering the effect of promoting learning through new business development experience.