The aims of this research were to find out the teachers’ strategy and obstacles in preparing their students to win storytelling contest. This study was designed using case study and qualitative method. The results of the study were collected through interviewing the teachers in five schools in Banda Aceh and Aceh Besar who were purposely selected by their achievement in preparing the students in some storytelling contests. The instrument of this research was the interview guide. The data were analyzed by data condensation, data display, and data conclusion. The conclusion of the study illustrated that the preparation process conducted by those teachers were motivation, recruitment, and coaching process which consist of modeling, observing and giving feedback. Meanwhile, the teachers’ obstacles to preparing students for storytelling those obstacles are students’ lack of motivation, lack of time, lack of discipline and the challenge to the diversity of students’ personality.