Discover essential reads for CISOs in this curated list of books covering cybersecurity leadership, risk management, zero trust, board communication, and more.
Why CISOs Fail, 2nd Edition
Author: Barak Engel
Barak Engel expands on the ideas from his original 2017 book, offering a fresh perspective on why security leaders struggle to make a lasting impact. With a central thesis that security is more about human behavior than technology, Engel challenges traditional views of cybersecurity management. This updated edition revisits key areas where CISOs often falter—spanning business enablement, sales, legal, compliance, technology, and executive leadership—while introducing new insights into the evolving landscape of security leadership.
In this edition, the author introduces two concepts: “digital shrinkage,” a novel way to assess and manage security risks, and the transition from CISO to CI/SO, a shift in mindset that redefines the role of security leadership. Presented in his signature conversational and humoristic style, this book is as entertaining as it is insightful.
The Business-Minded CISO: Run Your Security Program Efficiently
Author: Bryan C Kissinger
As AI reshapes cybersecurity, corporate security leaders must adapt to new threats. The increasing use of AI technologies within organizations and their exploitation by threat actors demands a fresh approach to IT risk and information security management. With cyber terrorism, regulatory pressures, and customer privacy concerns intensifying, corporate boards and senior executives are looking to business-minded CISOs to safeguard critical infrastructure and sensitive data. This book provides essential insights into how security leaders can navigate these challenges while aligning cybersecurity strategies with business objectives.
Offering a practical roadmap for IT risk and security professionals, the book guides readers through every stage of cybersecurity leadership. From preparing for the CISO role and making an impact within the first 90 days to structuring, advocating for, and operating an effective security program, it delivers actionable strategies tested in real-world scenarios. Whether you’re stepping into a new security leadership position or seeking to refine your approach, this book equips you with the tools needed to build a resilient, business-aligned cybersecurity program and drive long-term success.
The CISO Evolution: Business Knowledge for Cybersecurity Executives
Authors: Matthew K. Sharp, Kyriakos Lambros
This book provides a roadmap for security leaders seeking to bridge the gap between cybersecurity and executive decision-making. Through real-world examples and expert insights, the authors illustrate why aligning cybersecurity with business objectives is essential for driving meaningful outcomes. The book emphasizes the need for cybersecurity leaders to develop strong business acumen and demonstrates how they can effectively communicate risk, resource allocation, and security’s role in broader strategic initiatives.
The CISO Evolution focuses on executive presence and communication and helps technology professionals navigate common challenges when engaging with senior leadership. The authors offer actionable guidance on setting expectations, securing necessary funding, and positioning cybersecurity as a critical business enabler rather than a technical afterthought.
Project Zero Trust: A Story about a Strategy for Aligning Security and the Business
Author: George Finney
In Project Zero Trust, George Finney delivers an engaging and practical guide to implementing zero trust security. Rather than presenting a dry technical manual, the book unfolds as a fictional narrative centered on a newly appointed IT Security Director responding to a breach at his company. Through this compelling storyline, readers gain an understanding of zero trust principles, learning how to proactively protect their organizations by limiting the impact of cyber threats.
The book introduces John Kindervag’s five-step methodology for zero trust implementation, along with four key design principles that help organizations align security with business objectives. Finney debunks common myths and pitfalls surrounding zero trust, including misconceptions about cloud security and cost concerns. This is an essential resource for IT leaders, network engineers, system administrators, and project managers looking to implement a more resilient and efficient security strategy.
A CISO Guide to Cyber Resilience: A how-to guide for every CISO to build a resilient security program
Author: Debra Baker
The author draws on over 30 years of experience to help CISOs strengthen their organization’s security posture and protect critical data. A detailed analysis of a ransomware attack on the fictional company BigCo will teach readers how to implement fundamental security policies and controls to mitigate cyber risks. The book offers practical insights covering key topics like zero-trust architecture, managed detection and response, security baselines, and data classification.
Designed for both aspiring and experienced CISOs, as well as directors of cybersecurity and information security, this book provides actionable strategies to build, manage, and enhance a resilient cybersecurity program. Readers will gain expertise in defending against ransomware and phishing attacks, implementing security awareness training, maintaining offline backups, and prioritizing patch management. By the end, they will have a framework for embedding security policies into business operations and reducing cyber risk.
How to Measure Anything in Cybersecurity Risk
Author: Douglas W. Hubbard, Richard Seiersen
The authors expose the flaws in traditional cybersecurity risk management and offer a data-driven approach to making more informed security decisions. The book challenges conventional wisdom by revealing how many widely accepted risk management methods actually introduce more vulnerabilities than they prevent. By critically analyzing these shortcomings, the authors provide alternative techniques that enhance measurement, improve decision-making, and ultimately strengthen an organization’s cybersecurity posture.
The book serves as both a wake-up call and a practical guide for security professionals and business leaders looking to refine their risk management strategies. Readers will learn to identify ineffective security practices, implement quantitative approaches to risk assessment, and recognize when certain methods are too flawed to salvage. With a focus on actionable improvements and measurable results, the book empowers organizations to move beyond outdated “best practices” and embrace a more rigorous, evidence-based approach to securing their digital assets.
The CyberSecurity Leadership Handbook for the CISO and the CEO
Author: Jean-Christophe Gaillard
In this book, veteran information security advisor JC Gaillard explores a critical issue at the heart of many high-profile data breaches: the failure to implement basic cybersecurity practices. Drawing on years of experience advising top executives, Gaillard examines why even large organizations struggle with information security, often due to outdated systems and overlooked vulnerabilities. This book not only dissects these security lapses but also provides concrete steps that companies can take to strengthen their defenses.
Spanning articles written between 2015 and 2022, this handbook offers a look at how businesses can improve their resilience against cyber threats. Gaillard highlights the risks of digital transformation efforts that ignore foundational security principles, emphasizing the need for CISOs and CEOs to align cybersecurity with business strategy. Through expert analysis and actionable advice, the book serves as a practical resource for executives aiming to bring their organizations in line with modern cybersecurity best practices and close critical gaps in their defenses.
The Aspiring CIO and CISO: A career guide to developing leadership skills, knowledge, experience, and behavior
Author: David J. Gee
This book offers a targeted 90-day plan to help new CIOs and CISOs set themselves up for success, covering both the technical and strategic aspects of leadership. More than just a career roadmap, it provides mentorship-style insights for individuals unsure about their readiness for the C-suite, making it a must-read for entry-level, mid-level, and senior managers looking to advance.
Beyond technical expertise, The Aspiring CIO and CISO emphasizes the critical soft skills and interpersonal dynamics required to thrive at the executive level. Gee addresses the challenges of leadership longevity, offering survival strategies to avoid burnout while excelling in high-pressure roles. Readers will also gain guidance on personal brand development, executive presence, and navigating corporate dynamics—key elements for any aspiring technology leader. By the end of this book, professionals will be equipped with the strategic mindset and confidence needed to navigate their career path toward the C-suite and beyond.
Premier CISO – Board & C-suite: Raising the Bar for Cybersecurity
Author: Michael S. Oberlaender
The author tackles one of the most critical challenges facing modern CISOs: effectively communicating with the company board and C-suite. This book provides a structured approach to mastering executive-level conversations, ensuring security leaders can present cybersecurity priorities in a way that resonates with top decision-makers. Beginning with an industry status quo assessment, the book then walks readers through the key discussions a CISO must have at every stage—before stepping into the role, while leading security efforts, and even after transitioning out. Alongside this, it offers market research on CISO compensation and lays out success factors to prepare aspiring security executives for the demands of the job.
Beyond communication strategies, Premier CISO debunks common industry misconceptions and provides a framework for navigating corporate leadership structures. The book explores the intricacies of board composition, leadership dynamics, and the critical relationships a CISO must manage. Step by step, it covers core topics such as regulatory changes, enterprise architecture, and the evolving role of SecDevOps. With insights into boardroom expectations and the key questions security leaders must be prepared to answer, this book is an indispensable resource for current and future CISOs striving to succeed at the highest levels of their organizations.
Confronting Cyber Risk: An Embedded Endurance Strategy for Cybersecurity
Author: Gregory J. Falco, Eric Rosenbach
This book presents a forward-thinking approach to managing the threat of cyberattacks. While attackers continuously evolve their tactics, many organizations remain stuck in outdated risk management strategies, leaving them vulnerable to increasingly sophisticated threats. This book challenges business leaders to move beyond short-term fixes and adopt a long-term resilience mindset.
The authors introduce the embedded endurance strategy, a systems-level approach that integrates cybersecurity into the fabric of an organization’s risk management framework. Using real-world case studies, they outline a ten-step process to address not just technical vulnerabilities, but also the operational, reputational, and legal risks associated with cyber incidents. The book concludes with thought-provoking “cryptograms” from the future, offering business leaders insights into the next generation of cyber threats.