A method and system are provided for conversational cognitive stimulation performed on an electronic device. The system conducts a lifelike motivational interview, using human speech synthesis, to assess a user's cognitive health, emotional state, topics of interest, sentiment, and overall well-being. This may be accomplished by analyzing vocal and verbal components of the user's responses in the motivational interview through linguistic and paralinguistic analysis. The system may further perform a method to train the user's cognitive abilities according to the results of the motivational interview. The training is customized to each user through customized tasks, questions, and a duration of the training. The system can track changes to the user's cognitive health, abilities, and other areas and make adjustments to the training to promote cognitive stimulation.