A computerized method of assessing a chatbot conversation includes: extracting one or more messages from the conversation; determining, based on the one or more messages, an existing business opportunity value score using a business opportunity state detector module; determining, based on the one or more messages, an existing user experience score using a user experience state detector module of the computing device; determining, based on the one or more messages, a future business opportunity value score using a future business opportunity predictor module of the computing device; determining, based on the one or more messages, a future user experience score using the future user experience predictor module of the computing device; calculating a composite score indicating whether human intervention in the chatbot conversation is desirable; and generating a display signal including a status indicator, for review by a human agent, reflecting a desirability of human intervention in the chatbot conversation.