Academic supervision has a very important role in implementing an effective learning process as an effort to improve the quality of learning at school. The duty and responsibility of the principal as a supervisor is to improve the professionalism of the teacher in the process of learning activities. This study uses a qualitative approach while the data collection techniques are done through participant observation, in-depth interviews, and documentation studies. This research was conducted in MAN 1 Trenggalek and MAN 2 Trenggalek East Java, Indonesia. The results of this study indicate that the headmaster in implementing supervision of learning, adjusting to the plans outlined in the supervision program, using instruments and observation sheets, using the principles of supervision, using techniques and approaches that are varied and implemented with a pleasant atmosphere. The Islamic school head takes strategic steps as an embryo of success in implementing the supervision of learning in the school.