The workforce of an organization plays a critical role for the success (or failure) of digital innovation; they need to have specific skills, which are required for creating the needed digital change. Therefore, organizations need to continuously upskill their workforce. Different ways to prepare and upskill the workforce for the digital future exist. However, a structured approach to guide organizations on how to retrain and upskill their workforce is lacking. In the light of this context, the research goal is to provide an action-oriented guideline in form of design principles supporting organizations to handle digital upskilling. To achieve this goal a hermeneutic literature review and semi-structured expert interviews as well as a focus group discussion have been performed to deduce design principles. Based on an applicability check proposed by Rosemann and Vessey [1] the usefulness and applicability of the resulting 15 design principles in organizations are validated.