In this article I explore the challenges faced in design practice, where the approach to inquiry depends on understanding the context as a whole with all of its interconnected parts, and its successful transformation from one developmental phase to another. The specific goal of this article is to reflect on the meaning behind and the significance of the Issue Mapping Strategy in the exploratory research process of problem finding and discuss challenges encountered in the process of discovery that might lead to invalid topics and thus to design process fallacies. Therefore, this article explores three major areas of concern—places of invention, process of invention and product of invention—where the risk for design process fallacies is greatest. The significance of discovering commonplaces of arguments and the process of reasoning that help to identify issues in problematic situations is discussed and examples are given. The Issue Mapping strategy is useful in all of the cases that focus on problem finding in complex environments and situations of uncertainty in human experience.