According to one embodiment, a self-service system is to provide self-support knowledgebase (KB) information to allow users to navigate the self-support KB. A monitor is to track user interaction with the self-support KB while a user navigates through the self-support KB. An answer engine is to receive a query from the user to ask a question and in response to the query, to identify a predefined response to the query in view of a set of dialog rules. The answer engine is to transmit one or more related questions that the user will likely ask based on the dialog rules and the user interaction. The answer engine further transmits an invitation to allow the user to initiate a live support session after a predetermined condition has been satisfied.