In contemporary businesses, effective leadership is largely dependent on management know-how. To achieve strategic goals, keep a competitive edge and enhance organizational performance, it is strictly important to apply managerial knowledge and skills to real-world scenarios. This is particularly true for those companies where experience and knowledge of workers, the so-called know-how, represent the core of the organization, such as in One-of-a-Kind Production (OKP) companies. An OKP company produces unique products according to each specific customer demand, thus, every product requires a customized design and production plan. In this context, knowledge plays a central role: the ability to quickly design a correct model and anticipate any production problem depends on the know-how of the company’s human resources.