With increasing growth of Digital Services design driving the Digital Economy the ability of traditional ICT Design and Delivery Waterfall Methods to accurately describe and effectively communicate what is actually occurring to Senior Executives and Stakeholders is rapidly diminishing. Traditional CEO’s, CIO’s, CDO’s , CEO’s and CFO’s are struggling to understand the radical implications of Digital Transformation as it sweeps across their Organisations and transforms core business processes, support models, relationships with Partners, Vendors and Customers one Transaction or Micro Service at a time. Traditional ICT Support Models, Architecture Frameworks and ways of thinking and interacting with Customers, Staff and Partners all need to be re-assessed in this new “Ecosystem” view of the Enterprise. The Semantic Gap Model demonstrates that high failure rates of many large complex ICT programs of work maybe the result of a gap in language and common shared understanding of Key Terms between ICT professionals and their key Stakeholders. More effective communication models, education in the Digital Economy and Agile Design Methods for C Level Executives and a shared Semantic Model to achieve common Digital Design Standards amongst ICT Professionals can all help to address this growing Semantic Gap.