While there is a general agreement on the need for tools, which guide the evolution of complex organizational systems, and while there already exists a wealth of tools and approaches for the measurement and management of complexity, it seems that in practice these approaches often fail to achieve the desired impact during transformation processes. Based on focus group data and based on related literature, we analyze the factors that hinder current complexity management systems from guiding enterprise transformations and contribute a set of design principles, which address these factors. In particular, it is important to be aware of the context, to use a consistent ontology, to pay attention to visualization and to raise awareness and support.