In this chapter, through the description of concrete examples drawn from a field study,1 our intention is to provide the reader with a detailed account of the application of the methodological approach presented in Chapter X. The example refers to knowledge management in software development. In particular, the aim of this chapter is to apply the methodology for the investigation and management of the grey knowledge created and elaborated by software development teams in the production of new software applications. The chapter focuses on the early stages of the process when development teams have to make a choice regarding the software life cycle model that best fits given constraints concerning ambiguity of the requirements, risks, costs evaluation and scheduling. A step-by-step application to a case-study of a software company is presented in order to illustrate the main critical methodological aspects.