A fundamental challenge and opportunity for risk and operational managers to improve significantly their activity is to adopt a holistic approach to decision-making by grounding their decisions on the effective knowledge, experience and capabilities of operators and their organization. The paper explains why accounting for human and organizational factors is fundamental to strengthen decisions and why doing it in an experimental fashion is the way forward. Further, it is explained that leveraging on human and organizational factors, instead of appealing mainly to the technological ones, opens opportunities to improving decisions and save resources. The manuscript presents an example stemming from a use case developed with one major company of the Oil & Gas sector.