By transferring organizational learning concepts into the IT context, this paper provides a new behavior oriented foundation for managing IT organizations in the digital business transformation. As a practical contribution, the paper introduces a new management toolbox which supports Chief Information Officers (CIOs) to lead their Information Technology (IT) organizations towards ambidexterity in the digital business transformation. The organizational ambidexterity is required for the digital business transformation in order to contribute innovativeness while simultaneously assuring effective operational IT environment. The toolbox is constructed using the systematic concept analysis and the concept derivation methods to convert the organizational learning concepts into the dualistic CIO toolbox. The toolbox includes a set of traditional Key Performance Indicators (KPIs) to assure operational effectiveness and a set of leadership principles to enable an innovative and experimental organizational behaviour. The application of the new dualistic CIO toolbox is illustrated through hypothetical cases.