On the realm of knowledge transfer for enterprise incubation and corporate transformation, it is often desirable and relevant to offer distance, online, consulting. The preferred vehicle for achieving this goal is the world wide web, mostly a portal or web service. However, an assessment process of this type generally becomes impersonal and is quite lengthy. Therefore, it is unlikely an investor, or the owner of a small company, or even a staff member of a firm, will be prone to answer a questionnaire in a proper, effective, manner. The reason lies in the fact that most assessment methods require expert knowledge of the corporation and its native cluster, something most small businessmen will ignore to some extent, or else will be unwilling to disclose. As a result, it is probable that some sort of training, or coaching, will contribute to alleviate this problem. This will be done by presenting useful and pertinent information to the businessperson as she completes the corporate assessment questionnaire. This approach is targeted at true success factors appropiate for small and medium-sized companies. We present a rule-enabled, web-based, pedagogical web agent that offers key concepts and guidance during the session. The agent performs decisions based on domain knowledge and pedagocical information based on the user?s profile and observed behavior. The main objective of this approach is to make sure a correct set of data is saved when the process is completed. Such data will allow for better sustainment of the recommendations made to the entrepeneur.