Computer technology has been developed very rapidly in recent years and now computers are even replacing human in some areas. Use of judgment, however, is still very important in many other fields. Financial management is one of the areas that need managerial judgment and intuition while making decisions. In this study, we propose a methodology for designing a system to assist the decision maker (DM) in using his judgment to make effective decisions. The system also has to facilitate and enhance learning since judgment is excelled by experience. We specificly analyze decisions regarding the Debt Payment Planning (DPP) problem. This problem, which may be briefly stated as ‘development of an operational plan for the liquidation of debts’, is a new problem and does not exist in the literature. The analyses are conducted keeping in mind that the uncertainty of the financial environment and burden of inflation increase the complexity of the decisions. A model which we call, ‘Growth Model of Debt’ will be used in the analyses and a sample session will be shown to provide a clear understanding of the system operation.