A CISO is the ultimate guardian of an organization’s digital assets. As a cybersecurity leader, a CISO must possess a unique balance of executive leadership, technical knowledge, strategic vision, and effective communication skills. The ever-evolving cyberthreat landscape demands a resilient, proactive approach coupled with a keen ability to anticipate attack angles and implement protective security mechanisms. Simultaneously, a cybersecurity leader must navigate the complexities of balancing security requirements with business objectives, fostering a culture of cybersecurity awareness, and ensuring compliance with regulatory frameworks. The CISO Playbook aims to provide nothing but real-world advice and perspectives to both up-and-coming cybersecurity leaders as well as existing ones looking to grow. The book does not approach cybersecurity leadership from the perspective of the academic, or what it should be, but more from that which it really is. Moreover, it focuses on the many things a cybersecurity leader needs to “be” given that the role is dynamic and ever-evolving, requiring a high level of adaptability. A CISO’s career is touched from many differing angles, by many different people and roles. A healthy selection of these entities, from executive recruiters to salespeople to venture capitalists, is included to provide real-world value to the reader. To augment these, the book covers many areas that a cybersecurity leader needs to understand – from the pre-interview stage to the first quarter and from security operations to the softer skills such as storytelling and communications. The book wraps up with a focus on techniques and knowledge areas, such as financial literacy, that are essential for a CISO to be effective. Other important areas, such as understanding the adversaries’ mindset and self-preservation, are covered as well. A credo is provided as an example of the documented commitment a cybersecurity leader must make and remain true to.