Digital transformation can effectively support innovative strategic planning. However, it is necessary to realise that the digital ecosystem produces enormous volumes of data and creates unique requirements for working with it. Due to this, data needs to be integrated into the mindset and decision-making processes properly. The proposed solution is based on an analysis of digital transformation readiness models, analyses of the status of data and data literacy in the models and their extensions, a definition of the levels of readiness that need to be achieved, and preparation of educational programs for the enhancement of human digital transformation readiness from the mindset and skillset perspective. The main outputs of the chapter correspond to the problem and the suggested solution. They include the human digital transformation readiness index based on the capability maturity model (CMM), required mindset, and skillset, taking into account the digital and data literacy of the participants of innovation activities.