This article reports on an investigation of IS stakeholders communication and mutual understanding, and their impact on the success of business / IT alignment. In particular, by following a hermeneutic study of transcripts of two focus groups and several interviews conducted with senior business and IT executives, the paper explores the issues of modern business context and practices, project scope and structure, trust, language and nomenclature, and the barriers to the effective stakeholder communication and understanding. The study results are finally compared against the standard model of business and IT alignment. The main unexpected finding being executives' pre-occupation with issues of "marginal" value to the alignment model, such as day-to-day management of communicative and understanding effectiveness, as opposed to the fundamental issues of strategy and infrastructure fit.