The actual industrial revolution is bringing multiple opportunities of increased productivity through Cyber-Physical Systems, better cost control and decision making through Digitization and improved data communication chain through IoT. However, finding the best fit within Industry 4.0 context and writing the business case to support massive investments is not an easy task considering the organisations and the environment dynamics. The risk of disruptive implementation may be also high and involving massive implications. The paper proposes to highlight in a structured way . top-down approach . the key questions to address as an organization when leaving the awareness phase and preparing the implementation. This is a cross-industry study, covering as well different patterns: make to stock, make to order, engineering to order.