Over the past five years, the Ohio State University Libraries has made a series of strategic decisions and resource allocations aimed at significantly increasing the creation and responsible stewardship of digitized collections by centralizing the management of digital reformatting and overhauling the Libraries' digital collections infrastructure. As the digital reformatting program begins to mature and the organization prepares to migrate legacy content to new local and remote repositories, now is an ideal time to develop and implement a meaningful, achievable strategy for assessing the outputs, values and impacts of these strategic realignments. This paper argues for the importance of assessing digitization and digital collection-building activities, explores some of the challenges associated assessing this work, and the range of methods and metrics that have been employed. The goal of this early research is to engage with past and ongoing work in this field in order to build a foundation for meaningful assessment of digitization and digital collection building at the OSU Libraries and other cultural heritage organizations looking to assess their own efforts in this area.