The main purpose of this chapter is to deep into the importance attached to the Information Systems for the proper formulation of the corporate strategy. After introducing the basis of the strategic planning tradition model, which suggests the subordination of the Information Systems (IS) to the Business Strategy, we propose a new model that views the IS as an strategic instrument suited for the strategy formulation stage, rather than operational tools for the strategy control phase. Success in the application of this model we call “Concurrent Business/IS Strategic Planning Model” will closely depend on the consistency, coherence and soundness of the IS, both internal and external. In order to contrast the level of application of this model, an empirical case-study fieldwork was undertaken to rise up some empirical evidence on the degree of alignment between the entrepreneurial practice and the theoretical model proposed. This last section contains the main results arising from the empirical analysis.