What executives say about failure reveals a deeper problem than cognitive bias. Despite extensive playbooks, global executives continually repeat material, costly mistakes. While cognitive biases explain how individual errors begin, this multi-stage study—incorporating in-depth interviews, a Delphi consultation, and a survey of 120 international executives—demonstrates that organizational dynamics explain why they persist. The authors identify five enduring, overlapping root causes of executive missteps: short-term bias, business-as-usual thinking, the pressure to appear right, stakeholder misalignment, and weak organizational cultures. Validated by 94% of participants, these systemic failures are actively reinforced by compressed CEO tenures, quarterly financial pressures, and corporate structures that stifle upward dissent. Ultimately, mitigating recurring leadership failures requires more than recognizing personal bias. Executives must intentionally design organizations to counteract it by embedding structured debate, crisis simulations, generative mentorship, and robust challenge cultures that prioritize long-term vision over short-term compliance.