This study aims to understand cross-cultural differences in managers' learning styles by comparing Japanese managers with US managers. For this aim, the present research empirically examined learning styles of 254 participants in total: 128 subjects of Japanese managers and 126 subjects of US managers. There are three findings that were obtained from this study. First, Japanese managers were more concrete and reflective than American managers in general. But this general learning tendency may be affected in accordance with types of business that managers engage with. Second, Japanese managers were more heterogeneous in learning styles, while American managers showed more homogeneity of learning styles. Third, in the aspect of balance and specialization on learning styles, American managers demonstrated more balanced learning abilities than did Japanese managers. These findings suggest that group oriented countries like Japan possess symmetry on collective learning styles and asymmetry on individual learning styles; and in contrast, individual oriented countries like the US hold asymmetry on collective learning styles and symmetry on individual learning styles.