Use of external coaches for school-based extracurricular sports activities has been promoted because of the lack of teachers who can coach expertly and the large burden placed on teachers when coaching and managing such activities. However, it has been reported that securing external coaches through human resources is difficult. To promote the use of external coaches, previous studies have suggested some possible strategies: 1) clarifying the role and status of external coaches, and promoting cooperative coaching with external coaches and teachers; 2) interactive collection and provision of information about external coaches and schools, and improving recognition of the mediation system; 3) improving the way external coaches are recruited, and setting a suitable trial period; 4) moderating institutional limitations for coaching frequency and number of coaches; and 5) holding workshops for external coaches. However, these suggestions were made from only an individual viewpoint (i.e. that of teachers, external coaches, and potential external coaches), and did not consider organizational perspectives. In Japan, there are some organizations that help recruitment of external coaches for school-based extracurricular sports activities. It is necessary to consider the opinions of these organizations to develop more realistic and concrete promotion strategies. Therefore, the present study explored in detail the trials, problems, challenges, and strategies of organizations in order to promote the recruitment of external coaches for school-based extracurricular sports activities. Face to face semi-structured interviews were conducted involving 15 individuals in 11 organizations (2 national and 4 prefectural organizations, 3 schools, 1 university, and 1 company) supporting the recruitment of external coaches for school-based extracurricular sports activities. The interviews contained questions asking details of the recruitment system, problems, challenges and management strategies. All interviews were audio-recorded with agreement from the participants. The transcript data were integrated into 7 trials and their details, problems, challenges, and strategies were described. The results indicated that in order to promote the engagement of external coaches, a number of factors were important, including building human relationships between external coaches and teachers led by teachers that could share information, interactive collection and provision of information through mediator and cooperation with other organizations, collecting information about external coaches and interviewing them before formal acceptance, keeping the coaching non-compensatory, holding workshops and creating feedback to promote communication and learning of external coaches, and considering the continuity of the trial. Knowledge of the various problems, challenges, and strategies from an organizational perspective would contribute to improvement of recruitment strategy. The results of the present study could also provide information that is beneficial for other organizations wishing to conduct similar trials.