The rapid digitisation of our society has been dramatically changing the nature of work. In this article, we investigate empirically the relationship between IT and the organisational capabilities in an effort to understand and envisage the organisational design in a digitised world. Using a dataset of listed Japanese firms, the relationship between IT investment/spending and the organisational capabilities (operationalised with the ‘organisational IQ (OIQ)’ framework) is evaluated by experts’ judgement and regressions. Out of five OIQ principles, evaluations by two methods concur for External Information Awareness (EIA) and Internal Knowledge Dissemination (IKD) (moderate IT impact), as well as Organisational Focus (OF) and Continuous Innovation (CI) (modest to marginal IT impact). The results for Effective Decision Architecture (EDA), nevertheless, are striking. The experts evaluate that IT does not impact EDA, while there was a significant negative regression (0.5%) between IT and EDA. Number of possible alternative interpretations were presented. One thing clear is that the relationship between IT and OIQ is not simple, but there is possibly a web of interconnected causalities. We concluded the article by proposing several research topics to further investigate this puzzle about the relationship between IT investment and the organisational capabilities, and its contributions.