This paper develops a new approach to dealing with qualitative reasoning processes involved in managerial decisions, drawing upon choice strategies that have been developed within the general framework of multi-criteria decision making. Issues such as choices under uncertainty and preference formulation are addressed. An MCDM DSS intended to assist in high-level management decisions must focus on helping the decision maker to properly define the problem by providing a structure to it and to dynamically evaluate the alternative courses of action. A conceptual architecture is developed and presented to propose a general model for designing decision support systems specifically designed to assist in MCDM in a managerial context. A commercial loan approval judgment case is described to illustrate the real-world situation where decisions are made under fuzziness and usually require a high degree of intuition and subjective judgment. Development of a prototype system intended to partially represent application of the architecture is described.