Cobb’s Paradox (Bourne, 2011) asks: ‘We know why projects fail; we know how to prevent their failure—so why do they still fail?’ This study immerses itself into a major Australian IT project in order to unearth the drivers of project failure. Several new and novel findings have emerged. Using Multi-Grounded Theory this research has developed models and rich descriptions of new phenomena. The phenomena identified in this research, are drawn from social psychology and economic theory and highlight the issues of project execution as a social undertaking. This paper addresses one of those findings, namely the lack of domain expertise by senior management and vendor representatives. This paper examines the consequences of ‘actors-working-in-organisations’ (Manning, 2008, p. 678) and in particular looking at individual interactions, decisions and consequences (Goffman, 1959) through the lens of the Kruger-Dunning Effect (1999).