In this article, a theory-driven approach for managing the alignment process between business and IT by making high-quality IT investment decisions is developed. The aim is to increase the understanding of the dimensions of the alignment problem and to offer some support in solving it. The conceptualization of the alignment issue is searched from the structural alignment theory, arising from and applied in psychology. After the theoretical considerations, the article adopts a multidimensional and constructive approach to the alignment problem and looks for answers to the question: How should organizations align business and IT, or at least, how to support the business and IT alignment decisions? As a result, a theoretically sound framework originating from the alignment problem is proposed for the evaluation of IT investments, a methodology based on that framework, and a concrete investment support system to help decision makers. The applicability of the approach is evaluated in the context of an actual case in the finance sector.