This study provides a critical assessment of the current KPI-driven steering practices carried out by Chief Information Officers (CIOs). It explores how the use of ITIL KPIs affect the IT Service Management (ITSM) organization’s learning behavior and how this behavior impacts on Digital Business Transformation. The results indicate that, when used to steer the ITSM organization, ITIL KPIs will reduce the organization’s willingness to transform the current ITSM environment (i.e. current processes, work routines, services, policies and technologies) into the digital era. The findings suggest that, in order to successfully manage Digital Business Transformation, CIOs will need new types of management techniques which would endorse the organization’s norm-challenging and innovative learning abilities but also assure the operative effectiveness of the ITSM environment.