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In this conversation, Matthew Webster and John Checco delve into the complexities of cybersecurity governance, focusing on the importance of aligning cybersecurity with business strategy. They discuss the concept of Return on Security Investment (ROSI) and its critical role in decision-making processes. The dialogue emphasizes the need for effective communication with stakeholders, the integration of emotional intelligence in cybersecurity practices, and the importance of empowering business units to take ownership of cybersecurity responsibilities. The conversation also touches on the challenges of quantifying risks, the necessity of flexibility in cybersecurity implementations, and the evolving nature of ROI models in the context of cybersecurity investments. Takeaways Cybersecurity should be viewed as a strategic business asset. ROSI is essential for justifying cybersecurity investments. Quantifying near misses in cybersecurity is challenging but necessary. Engaging stakeholders is crucial for effective cybersecurity governance. Empowering business units enhances cybersecurity effectiveness. Emotional intelligence plays a key role in cybersecurity communication. Decision analysis can improve cybersecurity investment strategies. Resiliency is more important than efficiency in cybersecurity. Operational risks should be communicated in business terms. It's acceptable to acknowledge failures in cybersecurity initiatives.