Enterprises are continuously evolving systems; this evolution can be directed or emergent. Enterprise transformation has special aspects due to the enterprise being a socio-technical system whereupon evolution happens on the levels of individuals / humans / organisation, on the level of the technology and on the level of the Information Systems that integrates the activities performed by humans and by technology. Furthermore, changes are typically continuous, due partly to external factors and partly to strategic foresights. Either way, transformation needs to happen so that the enterprise can keep satisfying its objectives. An important transformation mechanism is to perform mergers or acquisitions (M&As). Interestingly, literature reveals that an unacceptably high percentage of M&As do not achieve the aimed objectives and (as we demonstrate) the success of such trajectory depends on several factors. This article proposes a methodology to overcome potential problems by making necessary anticipatory transformations opening up a possibility to perform M&As with a better chance of success.