How wasit possible that a giantlike Microsoft,totally focused on software, with a strong hold on business clients and productivity applications, decided to dive into a journey made of hardware, young consumers, and entertainment? How did it happen that Microsoft developed a totally new platform, the Xbox, with an operative system that was incompatible with Windows, its incumbent core technology? Despite a widespread advocacy aboutthe need for business transformation, very few organizations are successful in implementing a transformation change strategy like the one that transformed Microsoft. There are arguments that innovation is at the heart of triggering business transformation. A common thread in recent innovation studies isthat innovation comes from a diffused process of ideation. This perspective assumes that the major challenge for innovating is to have a good idea; once the idea is created, its value can be easily recognized by executives and developed by the organization. This perspective has prompted corporations, and scholars, to improve their waysto generate ideas. This orientation also has spurred a significant interest on how to foster the creativity of individuals, through design thinking, and the development of tools and methods to enhance thinking ‘‘outside of the box’’.