Due to the high volatility in the field of information technology (IT) and the rapid technological advancements, all IT professionals constantly have to be able to evaluate trends and put them into context. This is especially true for those who fulfill the role of a company’s chief information officer (CIO). But if there is a gap between the required set of skills and those needed, training becomes necessary. In order to plan training programs, one has to know the skill set of current CIOs. We investigate this by conducting workshops with 21 CIOs from a diverse set of companies. The purpose of this paper is to better understand the skill items of CIOs and how they interrelate.