This paper describes a study which explored how intentional reflective dialogue with an interlocutor can deepen Learning Advisors’ (advisors’) reflective learning in terms of their own professional development (PD). As one of the key roles of advisors in self-directed language learning is to activate learners’ reflective learning processes, it is worthwhile for advisors to experience reflective learning process for themselves as a part of a PD program. Eight advisors, with experience ranging fromone to three years, participated in this study. Each had two interviews with the interlocutor (the author). Although most of the advisors often self-reflect and have conversations regarding advising with colleagues, the reflective dialogue which was intentionally structured for training purposes resulted in advisors being engaged in a different type of self-reflective approach. The results of the study showed there are potential benefits for developing a continuing PD program for experienced advisors by introducing the reflective dialogue.