The design and implementation of a new Knowledge Enabled Engineering (KEE) in the context of a Virtual Enterprise is a labour intensive and risky task. In order to check, before embarking on a full-scale implementation, if the system will satisfy initial expectations, physical prototypes (Pilots) have to be tested in a near real usage environment to obtain qualitative and quantitative information for the final tuning activity. This paper proposes a methodology to guide this Pilot specifications definition process. The main aim of the roadmap proposed is to support the KMS design team in configuring a Pilot solution able to provide valid feedbacks of final system behaviour both from a software and non-software point of view.On one side the methodology guides the definition of Pilot implementation specifications from a technical perspective. It helps engineers and knowledge experts in selecting, refining, merging and cascading down the initial heterogeneous Pilot high level objectives to a lower level, and in elaborating a functional description of the KMS prototype. It proposes, moreover, a structured framework to classify KMS' performance indicators to help the Pilot task force in properly carry out the validation task.The methodology, on the other side, pushes the design team in considering those behavioural and methodological issues that arise from the necessary change in work practice as a result of implementing the KMS within a Virtual design environment. In parallel with the definition of technical specifications, the roadmap supports knowledge experts in developing and testing a set of Knowledge Management guidelines, intended as a list of Best Practices and Lesson Learned aiming to help users in utilizing the potentialities of the new solution.The methodology has been developed within the European project VIVACE to support the design and implementation of a new KEE system in the aeronautical domain.