This study was an attempt to explore the dialogue/dynamics between a counseling supervision and a supervisee and see what contents would emerge. The data collection was near 8 months, and the written records of both the supervisor and supervisee were collected after each supervision time. The supervisor has been a counselor as well as supervisor for over 20 years and the supervisee has practiced as a counselor for more than 10 years. The results show that the discussed themes were: self-efficiency, counseling atmosphere’s controlling, crisis clients or related party’s pressure, clients’ issues, anxiety which caused by clients, therapeutic relationship, and case-managing problems; supervisee’s personal issues (self-care and being manipulated by clients) and gains (counseling style’s change, solution strategies and thinking expanding, counseling is not working alone but requiring systems cooperation, counselor’s position and attitude toward others, counselor’s attitude toward clients, and examining counselor’s values); supervisor’s gains ( integrating case conceptualization via discussing, perceiving the meanings of helping profession, seeing different counseling styles, and the clients as the best teachers) as well as the possible barrier in supervision (power hierarchy and supervisor’s urge to assist).