Every year, successful software development organizations are faced with new development tools, new languages, and entire new computing paradigms from which to choose. As IT managers try to evaluate the impact of new technology in meeting the company's business goals, they must weigh not only the merits of the technology but their ability to successfully transition their developers to these new methodologies. If developers can't be transitioned, then other choices must be made, include hiring different developers or choosing not to implement the new technology. This chapter examines many of the issues surrounding the successful transition of developers to new methodologies and makes recommendations as to how best to do so.