Three studies of the work of outstanding designers in engineering and product design are reported—one protocol study and two interview studies. The engineering designer Victor Scheinman participated in a protocol study based on a small design task. The product designer Kenneth Grange and the Formula One racing car designer Gordon Murray provided interview studies covering their work. This chapter presents an example of each of these outstanding designers’ approaches to a particular design problem that they faced. Comparisons are drawn between the three examples, and there appear to be some striking similarities in their adoption of a strategic design approach, despite the very different project examples. A general descriptive model is developed from the examples, showing how creative design thinking operates across three levels: low level articulated knowledge of first principles, an intermediate level of tacit personal and situated knowledge applied within the particular problem and its context, and high level implicit and explicit knowledge of problem goals and criteria. All three outstanding designers seem to exercise this strategic approach in similar ways in creating novel design proposals, across a very diverse range of projects.