Many small businesses are quite entrepreneurial in their operation, and are prepared to consider the advantages conferred by information technology. On the other hand, some are still quite happy to continue to do things in the same way they always have, and see no need to investigate use of this technology. How and why these businesses differ in this way, and why they adopt some technologies and not others, is investigated in this chapter. The introduction of a new information system into a small business, or the upgrading of an existing system, should be seen as an innovation and so considered through the lens of innovation theory. The most widely accepted theory of how technological innovation takes place is provided by innovation diffusion, but most of the research based on this model involves studies of large organizations or societal groups. This chapter argues that another approach, that of innovation translation, has more to offer in the case of innovations that take place in smaller organizations–those employing less than 20 people (Burgess, Tatnall, & Darbyshire, 1999).