AimThe chronic lack of obstetrics‐gynecology (Ob/Gyn) doctors is a serious problem to be tackled in Japan. To address this issue, it is necessary for medical students to be interested in working as an Ob/Gyn doctor and more junior residents need to specialize in Ob/Gyn. This study aims to identify the preferences concerning working conditions among students and discusses what information should be provided and what conditions should be changed.MethodsA questionnaire survey was conducted among participants in the Summer School 2023 of the Japanese Society of Obstetrics and Gynecology. The respondents were medical students and junior residents interested in Ob/Gyn. Ob/Gyn specialists contributing to the summer school were also asked the same questions for comparison. The resulting data focused on important working conditions, concerns about future work, and expected future working conditions.ResultsResponses from 132 medical students (97.8%, N = 135), 122 residents (99.2%, N = 123), and 76 specialists (95.0%, N = 80) were obtained. There were three main findings. First, large gaps between students/residents and specialists were observed in terms of preferences. Second, differences between male and female students/residents were not negligible, although the difference was relatively small in specialists. Third, students/residents were more concerned about risks related to medical malpractice than specialists.ConclusionsGaps in preferences and perceptions regarding working conditions between students/residents and specialists should be narrowed through sufficient information provision. Working conditions should become gender‐inclusive rather than focus on female persons.