For the past several years we have watched with increasing dismay at the increasing chasm between information technology (IT) groups and their business counterparts. From where we sit, both sides have legitimate beefs: IT complains that, despite the increasing penetration of technology into every nook and cranny of the business, it doesn’t have a seat at the table and no one understands how difficult their jobs are given the constraints under which they operate. The business complains that IT doesn’t understand the business, consistently overpromises and under-delivers, and slows innovation. CEOs, following the advice in Nicolas Carr’s famous HBR article, “IT Doesn’t Matter,” perceive little strategic opportunity in IT and devote as little time as possible to the issues. Finally, the usual calls for IT to get closer to the business only exacerbate the situation. Neither side fully appreciates how difficult this is. And half-hearted efforts are akin to putting in just enough energy to jump halfway across the stream.