Successful IT organizations are ones that can constantly transform themselves to adapt to the changing environment. Unlike the punctuated change in traditional organizations’ transformation, IT organizations’ transformation is often a continuous change where the existing and the new business coexist. The ability to simultaneous exploit the existing business while exploring the new business during organizational transformation, which we term transformation ambidexterity, has proven to a key success factor. This study intends to explore how IT organizations develop transformation ambidexterity. We conduct a comparative case study of four leading IT organizations that have just gone through a successful transformation and unveil four development approaches, namely partition, hybridization, self-extension, and self-generation. These four approaches are based on two primary dimensions of ambidexterity development: 1) development mechanism and 2) development path. We conclude with theoretical contributions to IS, organizational transformation and ambidexterity literature and with guidelines for IT and general managers to redeploy appropriate mechanisms and follow appropriate path for ambidexterity.