Any digital transformation requires significant changes across many dimensions, ranging from operating models to funding models to platform architecture, among others. In this article, Eric Willeke argues that keeping these changes aligned can be one of the hardest elements of digital transformation, especially when organizations try to sidestep the challenge of evolving their current technology organization to the required level of capability by creating a new, “digital” organization instead. Such attempts fail to address three problem areas that can trip up any digital transformation effort: fragmented value streams, poor decision governance, and inadequate management of the business capability portfolio.