IT (Information Technology) outsourcing has become a standard approach for many Fortune 2000 and smaller companies to achieve cost-effectiveness. However, while outsourcing at the low end of the value chain has gained acceptance, many issues remain unresolved at the high end of the IT value chain. We develop a characterization of outsourcing firms, suppliers, and tasks that is useful in providing guidelines on when to outsource, and whom to outsource to. These guidelines for IT outsourcing strategies are based on a study of US customers, and Indian IT suppliers, involving questionnaires and interviews. To our knowledge, this is first study that has captured the supplier characteristics in the level of detail, which will be discussed by Dr. Akella in his talk.