A computer-implemented method is performed during an online chat session between a customer service representative (CSR) of a merchant, and the merchant's customer. Conversational text of the session is analyzed to determine a mood of the customer. Previously collected information about the customer is accessed, from a database that stores information about customers of the merchant. A tip is determined and sent to be displayed to the CSR. The tip is determined based on the mood and the accessed previously collected information. Other embodiments are also described and claimed.