We are studying a cooperation style where multiple speakers can provide both advanced dialogue services and operator education. We focus on a style in which two operators interact with a user by pretending to be a single operator. For two operators to effectively act as one, each must adjust his/her conversational content and timing to the other. In the process, we expect each operator to experience the conversational content of his/her partner as if it were his/her own, creating efficient and effective learning of the other’s skill. We analyzed this educational effect and examined whether dialogue services can be successfully provided by collecting travel guidance dialogue data from operators who give travel information to users. In this paper, we report our preliminary results on dialogue content and user satisfaction of operators and users.