The engineer of the future will face challenges that require much broader skill sets than those honed in typical engineering coursework. Much of engineering education is based on applying problem solving skills in instances where there is an accepted paradigm. However, when novel problems arise and a prevailing paradigm ceases to work properly, past problem solving skills will only result in repeating past behavior with inconclusive or flawed results. In a time of constant change, engineers must learn to identify when the prevailing paradigm is flawed, and successfully manage such situations in order to solve the challenges that lie ahead in the future – problems that don't yet exist. To develop such skills educators must provide educational experiences that motivate students at both a cognitive and metacognitive level to recognize such conditions so they can tackle these ambiguous problems and unstructured environments in a well-structured, organized manner. One way to provide such educational opportunities is by implementing a case study specifically designed for those learning outcomes. Through this research the investigators developed a series of case studies as a means to achieve the aforementioned outcomes. The results from the implementation of one of those cases in an entrepreneurship and business strategy in engineering course are discussed in this thesis.