IT leaders have long embraced the idea that the role of the IT unit, and of enterprise IT systems, is to enable business. However, when we ask CIOs how their “enabling” is going, they consistently respond that sometimes it goes well; sometimes not so much. In the digital economy, as IT becomes ever more integral to the strategic initiatives of firms, “sometimes” is not good enough. Companies cannot fritter away their valuable resources, whether in the form of money, systems, or most importantly, people.