This study used structured group discussions (The Delphi Method) among three groups of contracting professionals from the Air Armament, Aeronautical Systems, and the Electronic Systems Centers in order to identify potential roadblocks to implementation of Evolutionary Acquisition strategies. The Delphi groups also tackled the problem of identifying and exploring potential business strategies that may counter the identified challenges. Discussions revealed that current laws, regulations, and internal processes pose challenges in an evolutionary acquisition environment. No single business strategy emerged as the best way to implement the EA strategy. Participants suggested that all three Centers concluded that robust business planning, pre-contract agreements between the Government and the contractor, long-term relationships, and encouraging team behavior are key factors.