In the UK, 88% of companies utilise some form of outsourcing of their Information Technology (IT) operations. The evidence from the literature indicates that approximately 50% of these outsourcing decisions results in complications and in some cases failure. There is a need for outsourcing management frameworks to provide strategic direction and guidance in the decision-making process. This chapter describes the application of one such framework, known as the Holistic Approach {Business, Information, Organisation} (HABIO) framework, to two major commercial organisations indicating financial assessment, monitoring information for performance and quality of service which can be incorporated into service operations and benchmarking criteria.