The author aims at developing a better understanding of unstructured strategic decision making processes and the conditions for achieving successful decision outcomes. Specifically he investigates the processes used to make CRE (Corporate Real Estate) decisions. To reveal the fundamental differences between CRE decision-making in practice and the prescriptive ‘best practice’ advocated in the CRE literature, a study of seven leading Italian management consulting firms is undertaken addressing the aspects of content and process of decisions. This research makes its primary contribution by identifying the importance and difficulty of finding the right balance between problem complexity, process richness and cohesion to ensure a decision-making process that is sufficiently rich and yet quick enough to deliver a prompt outcome. While doing so, the study also provides more empirical evidence to some of the most established theories of decision-making, while reinterpreting their mono-dimensional arguments in a multi-dimensional model of successful decision-making.