Although organizational innovation with information technology (IT) is often carefully considered, bandwagon phenomena indicate that much innovative behavior may nevertheless be of the “me too” variety. In this essay, we explore such differences in innovative behavior. Adopting a perspective that is both institutional and cognitive, we introduce the notion of mindful innovation with IT. A mindful firm attends to an IT innovation with reasoning grounded in its own organizational facts and specifics. We contrast this with mindless innovation, where a firm’s actions betray an absence of such attention and grounding. We develop these concepts by drawing on the recent appearance of the idea of mindfulness in the organizational literature, and adapting it for application to IT innovation. We then bring mindfulness and mindlessness together in a larger theoretical synthesis in which these apparent opposites are seen to interact in ways that help to shape the overall landscape of opportunity for organizational innovation with IT. We conclude by suggesting several promising new research directions.