At inception, much design activity is unstructured and as such is faced with an array of uncertainties. If not addressed early enough these uncertainties can gestate into undesirable outcomes which the design team will find difficult to redress at later stages in project—especially, where the project is constrained by resources (time, money, people). In order to militate against such circumstances occurring the design team has to understand both the nature of the problem facing it and the nature of the uncertainties contained within the problem space. These issues impact not just at the creative, early stage of the project but across the design spectrum. The chapter begins by identifying the main elements within this spectrum; creativity, innovation and the oft-neglected execution phase. Two core conditions that designers have to come to terms within this process, are then explored: how can problems be categorized and which of these variants is the most problematical? The second condition addresses the nature of uncertainty when applied to the more intractable end of the problem scale. In response to design situations governed by these two conditions, methods that support decision making and mitigate risk are introduced under the broad category of Problem Structuring Methods (PSMs). Within the gamut of methods available the authors then explore the particular value of two methods which operate best when faced with qualitative judgment rather that observed metrics; morphological analysis to help generate and identify viable possibilities followed by Multi-criteria Decision Analysis which can help position these possibilities in a hierarchy. Finally, an argument is posited that the design process or system has to take into account an understanding of the business model for the designed item as this can impact success or failure at the execution phase when the end product is introduced to the end user. Early consideration of the business model (in all its variety) can redress some of the inherent uncertainties during the overall design process.