Since the 1950s the process of introducing IT into work organisations has been marred by reports of significant underperformance and failure. While it emerges that such underperformance and failure is due, in no small way, to an inability to effect integrated strategic change, it is unfortunate that much IT related inquiry has failed to adequately address this dilemma. Acknowledging the weaknesses of dominant positivist research approaches, this paper outlines the case for action oriented inquiry as a legitimate and profoundly important post-positivist family of research approaches relevant to investigating this enduring dilemma with IT.