Efforts in IS research have long sought to bridge the gap between the information technology (IT) function and strategic business interests. Efforts in IS research have long sought to bridge the gap between the information technology (IT) function and the strategic business interests. People perceive affordances (possibilities for action) in information technology artifacts differently as cognitive structures (schema) which bias individual focus. This study explores how an individual’s tendency to perceive the ‘trees’ in an IT ‘forest’ (artifact preference), affects their assessment of efforts to achieve more effective IT outcomes. The effect is demonstrated using a relatively simple IT success model. Further, in a sample of 120 survey responses supported by ten semi-structured interviews we demonstrate that job role and organizational IT complexity systematically impact artifact perception. A better understanding of IT artifact bias promises to help organizations better assess information systems.