An artificial intelligence (AI) system for guiding a user interaction in a phone call or chat session. The system includes a computer running an AI algorithm, such as a machine learning algorithm, which is trained to recognize patterns in user interaction dialog which lead to satisfactory outcomes for the user. The system may operate in a completely autonomous mode, or the system connect a human agent in the loop. The algorithm adaptively guides the dialog to achieve a favorable outcome based on the current status of the dialog—including identifying a next question to ask, information to provide, or an action to take. The algorithm is trained via supervised learning using real dialog transcriptions from past user interactions which have been supplemented with decision points and outcomes. After deployment, update training may be performed on the algorithm using data captured by the system after the user interactions.