A system, method and computer program product for evaluating a user's database (db) design schema and definitions syntax and generating a database score according to applied decision tree logic. The database design syntax is automatically evaluated and decision tree logic is applied to determine a context of the database design object and associated syntax and definitions statements. As a result of the automated evaluation, users may then obtain, via a user interface device, a detailed context information associated with their design to assist them in understanding how their database score was derived. By using this detailed contextual information, users analyze the results and can understand what changes can be made to improve their definitions Database Score. The system and method increases the ability of the user to create better database definitions by learning and improving using the contextual data returned.