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2025 Year in Review - Top 10

  • Phil Venables
  • 2 minutes ago
  • 4 min read

The most read posts in 2025 coalesced around the concept that successful cybersecurity is fundamentally a function of business leadership, strategic design, and sustainable execution. The unifying themes across the top posts emphasize shifting security from an artisanal, reactive craft to an industrial-scale, proactive capability focused on building scalable, self-reinforcing systems (flywheels). Transformation requires leaders to manage stakeholder expectations carefully, particularly by preparing executives for the "uncanny valley" where fixing foundational issues makes problems seem worse before they improve. Effective security executives communicate their mission using the language of risk, capital, and opportunity to maintain long-term alignment and attract necessary resources. So, here’s the top posts:


  1. Good CISO / Bad CISO. Good CISOs operate as business executives managing technology risk and take full accountability for organizational resilience, measuring their success by business outcomes. They define a crisp, generative strategy that inspires work across the organization, rather than confusing a list of projects or vendor purchases for a strategy. Conversely, Bad CISOs often function as IT managers focused solely on security tools, providing excuses instead of ownership, and running a constant fire fight rather than designing scalable systems.


  1. Cybersecurity Leader Job Description. This post redefines the security leadership role as a transformational business executive position designed to drive ongoing digital transformation and not just protect the organization. The core mission involves maximizing the safe use of digital assets, maintaining the company's freedom to operate, and ensuring security objectives are sufficient to mitigate evolving risks by embedding security into the business and engineering lifecycle. Essential outcomes include defining Key Risk and Performance Indicators (KRIs and KPIs), increasing efficiency through automation, and ensuring resilience and recovery processes are rigorous.


  1. Levelling Up Your Leadership. This post outlines the essential qualities for leveling up security leadership, asserting that success demands courage, discipline, and relentless perseverance. Key leadership practices also include ruthlessly prioritizing efforts toward high-leverage areas (platforms, core processes), taking personal accountability, and proactively managing stakeholder expectations.


  1. Starting a Security Program from Scratch. This post provides a four-phase maturity framework for establishing a new security program or substantially rebuilding an existing one. Phase 1 focuses on direction: securing executive sponsorship to drive change and establishing basic governance for tracking priorities and accountability. Phase 2 covers the basics: conducting a breach assessment, fixing high-risk results immediately, and performing a broad security review using frameworks like the NIST Cybersecurity Framework and CIS Critical Controls to develop a multi-stage implementation plan. Phase 3 focuses on making security routine through formal program management, continuous risk assessment, control monitoring, and increasing resilience through regular scenario testing. Phase 4 requires making security strategic by aligning controls with business objectives to reduce friction, improve customer experience, and support business agility.


  1. A Plan is not a Strategy. This post stresses the crucial distinction that a list of projects or "strategic planning" is not an actual strategy. A strategy is instead a short, coherent theory of winning that specifies the competitive outcome desired, whether against adversaries or in achieving compliant business results with minimal toil. Effective strategies focus on specific goals, such as achieving risk transparency and fast feedback to create demand-pull from leaders for controls, reducing the total cost of control (CapEx, OpEx) to raise the security baseline cost-effectively, and architecting solutions to defeat whole classes of attacks by shifting down and shifting left. 


  1. Security Leaders’ Reading List. This list compiles recommended reading materials for security leaders, noting that the most challenging aspects of the role: leadership, culture development, program management, and risk management are often addressed by books outside of classic security literature. 


  1. Post Quantum Cryptography. This post urges organizations to start preparing for the transition to Post Quantum Cryptography (PQC), given that Cryptanalytically Relevant Quantum Computers (CRQCs) are conservatively expected to arrive between 2032 and 2040. The critical factor driving this urgency is not "store now and decrypt later" attacks, but the sheer complexity and long timeline required for migration, likened to the Y2K efforts (PQ(2K)C). Objectives include developing a comprehensive inventory of cryptographic dependencies, setting procurement standards for PQC conformance, planning for hybrid operation, and implementing robust crypto-agility practices to ensure future algorithm changes can be managed routinely.


  1. Turning the Security Flywheel. This post applies the concept of a mutually reinforcing "flywheel" chain of activities to security programs, allowing them to gain momentum and scale effectively. Seven flywheels are proposed, including the concept of raising the baseline by using budget to design controls and then relentlessly reduce the total cost of ownership of those controls. Another flywheel involves industrializing security by moving from simple asset inventories toward a "digital twin" of the environment that can be policy modeled and enforced, creating continuous control monitoring. The overall goal is to build self-reinforcing systems that advance the security mission without requiring continuous intervention and toil from the security team.


  1. Career Longevity and the Don’t Fire Me Chart. This post explores why security program success is fundamentally tied to leadership persistence over the long term, noting that transitioning to a more defensible security architecture requires commitment over several years. A common challenge faced by security leaders is the "uncanny valley," where initially driving improvements causes things to appear worse before they get better because enhanced monitoring uncovers numerous previously unknown issues. This effect frequently leads to short-term CISO turnover, but the solution is simple: the CISO must proactively communicate to executives that this apparent deterioration is actually a sign of being on the right track toward sustained improvement, securing the long-term support needed to push through to a lower level of issues.


  1. The CISO Factories. This post examines the common characteristics of "CISO factories", organizations that disproportionately produce security leaders who move on to executive roles elsewhere. These organizations are defined by relentlessly modernizing their technology stack for defensibility, having long-tenured business and IT leadership to sustain multi-year transformations, and establishing federated security structures like Business Unit CISOs (BISOs) to provide crucial executive experience. They also cultivate a strong tone at the top regarding security investment, foster a clear sense of mission, and encourage deep technical leadership, mentoring, and disciplined attention to detail. These features create the organizational conditions necessary for security talent to emerge and flourish.




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© 2020 Philip Venables. 

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