Requirements elicitation has been identified by researchers as a highly critical and error-prone phase of IT development projects. Many challenges are rooted in the human and social dimension of this phase, which requires intensive communication activities between stakeholders with different backgrounds and perspectives. The conduct of a systems analysis supports stakeholders in reaching a shared understanding about crucial elements. The aim of this paper is to identify and describe recurring issues in requirements elicitation, and to better understand the potential of systems analysis efforts for addressing these issues. While literature provides plenty of high-level categorizations of requirements elicitation issues most often the argumentation is not complemented with concrete, real-world examples. Therefore five interviews with IT practitioners have been conducted in order to back-up a theoretical framework of problem areas elaborated by Saiedian and Dale (2000) with practical insights. This approach enabled a thorough analysis of four major issues in requirements elicitation covered by this research: Problem Perspective Differences, Resistance, Poor Communication and Articulation/Expertise Problems. Finally, a first linkage between a specific systems analysis method, the Work System Method, and its potential for addressing these problem areas has been established.