School-based extracurricular sports activities are beneficial for positive youth development. However, there is a shortage of appropriate in-school coaches, and therefore recruitment of external coaches has been considered as one solution to this. A previous study has reported four model strategies of organizational promotion to recruit external coaches. These four models included “compensational support”, “staff introduction”, “delivery of collegiate students”, and “cooperation with company”. In order to promote the further development and popularization of these organizational trials, user-side evaluation is necessary. Therefore, the purpose of the present study was to clarify the strengths and problems related to these four organizational promotion strategy models when recruiting external coaches for school-based extracurricular sports activities from the viewpoint of teachers. The participants were 12 teachers who worked in public junior high or high schools. All of them had experience of coaching school-based extracurricular sports activities. Face-to-face semi-structured interviews were conducted with the individual participants, and all interview data were transcribed. Then, similar meaning units were grouped into themes with respect to the four models, strengths and problems. As a result, many specific themes for each model emerged. For instance, with regard to “compensational support”, monetary support was regarded as a strength, although the early application period was a problem. With regard to “staff introduction”, adequacy for beginners was a strength, but lack of mediation organization was a problem. With regard to “delivery of collegiate students”, regular coaching was seen as a strength, but worry over not choosing a delivered external coach was a problem. With regard to “cooperation with company”, high coaching skill was a strength, but an expensive coaching fee was a problem. Additionally, comprehensive opinions about all the models were reported, such as lack of information about the system and the need for educational coaching. These similarities and differences in the results indicated the importance of mediation system design considering the regionality and situation of the school-based extracurricular sports activity. Effective publicity and re-examination of financial manager is also needed. In addition, mediation organization and teachers should arrange previous meetings with external coaches to understand their human qualities and educational attitude. Furthermore, it would be valuable to develop the quality of external coaches through previous training or workshops. Finally, changes in the application period for each mediation system are suggested.