The aimed of this research is to investigate the speaking skill problems in daily conversation faced by students of Pondok Pesantren Fadhlul Fadhlan (PPFF) from their own and their mentors’ perspectives. The method used in this research was descriptive quantitative. The population of this study was the freshmen students, senior students and the mentors at PPFF. By using simple random sampling, the researcher recruited 110 freshmen, 84 senior as the sample and all the 16 mentors. The instrument used in this research was questionnaire as the primer data supported by a semi-structured interview. The results of this study revealed that there were some speaking problems faced by students in daily conversation based on students and mentors’ perspectives. Those are not having sufficient grammar, insufficient time of speaking class, fear of making mistake, not having sufficient English knowledge, pronunciation, shyness and self-confidence. Furthermore, the independent sample t-test shows that there was no significant difference between the freshmen’s and seniors’ perspectives. The result of one-way ANOVA showed that overall there was no significant difference among the freshmen’s, the seniors’ and the mentors’ perspectives in the students speaking skill problems. This research pedagogically contributes to English teacher in determining the method and material for teaching. Knowing the students perceptions will help the teacher to achieve the goals of learning. Besides, by creating an interesting method and suitable material the teacher also can engage the students’ interest.