Enterprises are systems of systems that continuously evolve during their lifespan, be it in a directed or emergent way. As enterprises are in fact socio-technical systems, this evolution may occur in one or more specific areas - such as the human / organizational, the technology and / or the Information System that integrates the activities performed by humans and machines (technology). This paper addresses a special type of change, brought about by enterprise mergers or acquisitions (M&As). M&As are an important strategic transformation instrument in the hands of management; however, literature reveals that an alarming high percentage of M&As do not achieve their declared objectives. In this paper we attempt to a) demonstrate that the success of such strategic changes depends on several essential and largely overlooked factors, and b) outline a possible approach of building preparedness for M&As), so as to improve the chances of success. This paper also presents a retrospective M&A case analysis to demonstrate the types of potential problems that could have been effectively addressed by anticipatory transformation facilitated by the proposed preparedness building approach.