A conversation may be monitored in real time using a trained machine learning model to identify a desired outcome of a conversation and generate one or more phrases for accomplishing the desired outcome. A confidence score may also be determined for one or more phrases that indicates a likelihood that the one or more phrases may help accomplish the desired outcome of the conversation. In some examples, a confidence score may be based on whether an agent, a caller, or both responded unfavorably to a similar phrase used previously in another conversation. In other examples, a confidence score corresponding to one or more phrases may be based on whether a prior conversation in which one or more similar phrases was used resulted in the desired outcome being accomplished.