Japanese-speaking graduates are in high demand not only from Japanese companies but also from multinational companies, in order to expand their Japan-related operations and promote diversity. However, for university learners in Singapore, it can be difficult to achieve a high enough competency level to match their requirements because Japanese is only provided as an elective. Therefore, the authors conducted a three-week summer intensive programme aiming at preparing intermediate learners of Japanese for job interviews by collaborating with experts from a Japanese recruiting agency. Previous research shows that there are differences between the expectations and evaluation of business people and Japanese language teachers. Thus, we conducted this study to examine if there are gaps and to explore how to improve learners’ job interview performances. It was found from the mid-term test that the learners lacked ability in ‘Clarification Questions’, which is essential for interviews. Furthermore, it was found that although focused training in the second half of the programme helped to strengthen this skill, mastering it adequately within the programme duration was too difficult. This paper not only addresses the academic gap in current pedagogical practices but also connects with broader educational goals of equipping learners with skills that are directly applicable in real-life situations, including the workplace.