Business/IT (information technology) alignment can be considered as one of the key challenges of information management (IM). A vast majority of studies assumes an uni-directional alignment process that seeks to link the IT strategies to superior business objectives. However, there are plenty of market situations where the ability of an enterprise, or even entire branches, to adjust their business model to new IT developments is crucial to survive among their competitors. Not only under the umbrella of new buzz words like digital transformation and digital transition and their glaring examples such as media streaming, these competitive requirements have recently become more vital. Currently dominating business-driven alignment paradigms are seemingly not capable to accommodate these requirements to a full extent. In this chapter, the concept of bi-directional business/IT alignment is explained and defined by extending a well-known 3-layer model of IM. Furthermore, it is analyzed to which extent different IM models as well as common IT governance frameworks support this paradigm.