Organizational leaders are increasingly turning to design approaches as a panacea for uncertainty and disruption. However, frictions between design and typical engineering and management practices make integrating design into organizations difficult. To do this well, it is necessary to foster the co-evolution of two types of design capabilities: deep expertise in design practices and wide understanding, application and scaffolds of design. Underestimating the co-evolution leads to three typical “pitfalls” that can limit the effectiveness of investments in design. We discuss each of these tensions in the context of large technology companies, along with practical recommendations on how to avoid them.