A retraining service accesses conversational logs, each of the conversational logs recording a separate conversation, between a separate user and a conversational service, and at least one outcome identified with the separate conversation. The retraining service assess, from the conversational logs, at least one conversation gap and response with the at least one outcome matching a type of outcome that indicates the response impacted user experience in a negative way from among types of outcomes. The retraining service evaluates one or more recommendations for retraining the response to promote a positive type of outcome from among the types of outcomes. The retraining service outputs the one or more recommendations to the conversational service for directing retraining of the response by the conversational service.