This collection of excerpts from "Why CISOs Fail, 2nd" by Barak Engel offers a critical examination of the Chief Information Security Officer (CISO) role and the broader cybersecurity landscape. The text highlights how CISOs often struggle due to a focus on technology over business context, leading to miscommunications, ineffective strategies, and a perception as "fear merchants" rather than strategic partners. Engel argues for a reimagined CISO who understands business objectives, influences sales, and manages risk as an integral part of organizational growth, rather than merely enforcing compliance or technical controls. The book also critiques common industry practices, such as rigid compliance models and ineffective password policies, advocating instead for pragmatic, human-centered security approaches and recognizing that some losses are an inevitable part of doing business. Ultimately, it emphasizes the importance of communication, business acumen, and strategic integration for a CISO's success and overall organizational security.