The previous chapter demonstrated that information technology will drive digital transformation in companies with exponential performance increases. Digitalization will penetrate society and companies extensively, massively altering processes and organizations. These changes encounter a very heterogeneous buyer and employee population with different educations and experiences regarding digitalization. More and more customers and all current company entrants belong to the generation of so-called Digital Natives. These are people who have grown up with IT-based offerings such as computer games, the internet, and Facebook, as well as smartphones. The use of these digital offerings is natural for them and has shaped their behavior. At the same time, there are so-called Digital Immigrants, often skeptics, who struggle with this new world. For successful transformations, it is crucial to find ways to involve all participants and to inspire them for the inevitable upcoming changes and opportunities. This chapter delves into these challenges and shows solutions and trends.