Abstract: This chapter depicts a business process reengineering (BPR) initiative undertaken by a U.S. telecommunications company (TELECO) in response to imminent survival-threatening competitive pressures in its traditionally monopolistic market. The case study first highlights some of the seldom talked about problems faced during the redesign of business processes such as lack of detailed knowledge about functional areas, hidden agendas of top management, lack of knowledge of (and overreliance on) computer-based BPR tools, poor choice of metaphors in organizational language, and lack of communication. Thereafter, the case study identifies critical problems faced in implementing redesigned processes. These problems include difficulty creating an atmosphere of open communication, pressures against selecting information technology (IT) vendors on merit, lack of awareness of the lead times associated with IT, uncoordinated implementation of human resources and IT strategies, and discontinuities in leadership. Although we hope that the reader will individually derive lessons from the case for application in other contexts, we nevertheless provide a discussion on three issues (leadership, communication, and IT knowledge and management) that, in our opinion, significantly contributed to “failure” of the initiative at TELECO.