The continuous digitalization of modern organizations leads to increased exposure to digital threats. Consequently, safeguarding digital assets is central to the organization’s resiliency and cybersecurity, which are core business functions. Commitment from organizational decision-makers is crucial for good cybersecurity posture since they are responsible for allocating resources and prioritising cybersecurity. To underpin such commitment, decision-makers must be aware of the organization’s cybersecurity risks and digital assets. The subsequent challenge addressed in this research is to raise awareness among decision-makers. This research draws on previous research to develop a tabletop exercise designed to raise cybersecurity awareness among decision-makers. Using a multiple-case study research approach, the tabletop exercise was conducted and evaluated on six occasions with a total of 90 decision-makers from various industrial sectors. The general view of the participants was that the tabletop exercise was a good and engaging way to learn about cybersecurity. The main contribution of this research is that it outlines tabletop exercises as a promising approach to raising cybersecurity awareness among decision-makers. However, it is important that such exercises are designed so that enough time for discussions is allowed. Furthermore, this research identifies a need for more evaluations focusing on the long-term effects of tabletop exercises.