Systems and techniques for improved user prompting. A system according to one aspect of the invention includes a central server hosting various modules providing services to users. The modules suitably employ voice recognition in order to interpret user inputs. Each module has access to user information that includes information indicating the user's experience with each function of each module. When a module needs to issue a prompt to the user, it retrieves and examines the user information to determine the user's experience with the module and function. Suitably, each module is operative to categorize a user as belonging to an experience category, such as novice, intermediate and expert based on the user's level of experience with the function. The module selects a prompt associated with the user's level of experience with the function and presents it to the user.