People who own the enterprise content management effort in their organizations are facing a daunting task: thousands and thousands of documents and files, widespread involvement in creating content, ingrained practices for authoring and revising, enthusiasm for and resistance to change. How do you place your first bet on a project that will succeed in its goals and convince the organization that it’s worth the effort to tackle another clump of content? We provide a guide to assessing your content collections and a litmus test for choosing an initial project.