The present invention relates to an automated coaching system for financial modeling and counseling system. The automated coaching system enables the user to analyze the user's investment portfolio and dispense context sensitive automated advice to the user based on the user inputted financial data, preferences and financial goals. The automated coaching provides its advice to the user in syntactically correct natural language coaching strings and is able to configure and recommend solutions and financial products, specific to the user's situation. Furthermore, the automated coaching system can analyses the impact of the recommended product on the user's financial model.