This study was conducted by teachers at a university-affiliated school who teach practical student teaching every year. The teachers attempted to reflect on and analyze the instruction they provide using the self-study method. They interviewed two student teachers undergoing practical student teaching and analyzed their interview data by focusing on the student teachers’ expectations of the student teaching as well as any improvements and difficulties they experienced. The analysis revealed that the student teachers aim to master various target skills in their practical student teaching. A further finding showed that the student teachers aim to reflect on their practice to identify personal challenges and then work to overcome these challenges. The study also highlighted the factors that contribute to the improvement of the supervisors’ instruction. With regard to harmony and disharmony between trainees and instructors, the harmony between the two parties was associated with a shared understanding concerning the practical tasks targeted in the student teaching. Conversely, disharmony was associated with a lack of such understanding. These results imply that the key to overcoming these challenges entails that the teacher supervisor carefully differentiates between “instruction” and “coercion” with regard to the student teachers.