The HSD&E activities are supported by a central decision-making system (DMS) (in which a HR subsystem is included), knowledge management system (KMS), and an enterprise architecture project (EAP). The chapter's proof of concept (PoC) is based on a business case from the insurance domain where the central point is the capacity of the selected manager skillset to successfully start and finalize a BTP or an EAP (or simply a project). The PoC shows the selection process of a manager's skillset to transform the traditional insurance enterprise into an agile and automated enterprise. Projects are managed by managers, who are (or should be) supported by a methodology and a framework that can estimate the risks of failure of a project; at the same time, they should be capable of managing the implementation project processes.