This chapter provides a simple but effective method of ascertaining an organization's preparedness for undertaking and managing projects. Each project success failure level has a different responsibility thrust, objective and focus. Hence, the diagnosis of an organization's preparedness for undertaking and managing projects must collectively address these individual four success failure levels. The diagnostic questionnaire has been designed to make it user-friendly for respondents to complete. An effective project diagnostic model must take a holistic view. There is a tendency to relate projects and project management to the function of the project manager. The basic principle to keep in mind when devising an assessment scheme is that what cannot be measured cannot be managed and what cannot be managed cannot be changed. The major weakness being experienced by the organization is a lack of a standard project management methodology that is applied across the whole organization and ensuring that personnel are adequately trained in its use.