Tag: CyberDefense

Becoming an Effective Board on Cybersecurity

A board directorship is a prestigious appointment, signaling public recognition of an individual’s industry expertise, business acumen, and leadership qualities. According to PwC’s 2024 Annual Corporate Director Survey, 13% of board directors reported that their boards had added someone with cybersecurity expertise in the past year. Given a typical term of five years, most corporations should have dedicated board oversight of cyber matters. However, what does it take to be effective?

Among the many cybersecurity challenges, some argue that the board should focus on governance and strategy rather than technology and operations, even though these are integral to cyber safety. Certainly, a sensible approach is that the board neither interferes with daily operations nor loses touch with on-the-ground realities. However, an overly narrow focus on governance and strategy can backfire, overlooking volatile business and operational changes that leave the organization more vulnerable.

In the aftermath of a security breach, every cybersecurity chief is prepared to address the board’s anticipated inquiries: How did it happen? Who is affected? What are the damages? While the report may highlight technical missteps and lessons learned, it often sidelines underlying office politics and unclear risk ownership. To uncover these issues, the board must cut through technical jargon and probe deeper.

Given its fiduciary role, the board is best positioned to confront the most insidious aspects of cybersecurity, such as near misses, risk ownership, peer comparisons, and even the probability of being hacked—critical issues that rarely make it onto the agenda.

Focus on Near Misses

Today, many boards mandate incident updates within 48 to 72 hours. Some require the same for significant cyberattacks on critical services and infrastructure. Analyzing these cases helps identify weaknesses, refine security controls, and prevent future incidents.

Learning from actual incidents, however, is costly and painful, often reflecting poorly on performance. Instead, the board can learn from near misses—situations where threats were detected and mitigated before causing harm. Near misses are positive indicators, encouraging staff to strive for improvement rather than fear repercussions. When risk owners feel less defensive and more receptive to issues raised, the organization benefits. After all, understanding near misses confirms that safeguards are working as intended—or that luck played a role, prompting further scrutiny.

Identify the Risk Owners

Who owns cybersecurity risk? This is a compelling question for the board, yet it has no straightforward answer. While many assume the cybersecurity chief is the risk owner, this perspective is incomplete and can obscure deeper accountability issues within an organization’s hierarchy.

Cybersecurity is a long-tail risk, with repercussions that can span years. Consider a massive personal data breach: the organization could face prolonged lawsuits, hefty regulatory penalties, job losses, and the need for fresh capital to overhaul its defense strategies. Restoring reputation and customer trust could take years. Clearly, no single individual can bear full ownership of these risks.

According to ChatGPT, a risk owner in cybersecurity is responsible for managing and mitigating risks associated with a specific asset, process, data set, or business function—a definition I fully support. For example, corporate infrastructure is a tangible asset, payroll is a financial process, staff training is an HR function, and regulatory compliance falls under legal purview. These risks span multiple business leaders across technology, finance, human resources, and legal and compliance—each of whom is responsible for ensuring compliance and security within their domain.

By setting the tone from the top and clearly assigning ownership, the board can break down silos and prevent disputes over responsibilities in data protection, security controls, and cybersecurity exigencies.

Ask for Peer Comparisons

We are accustomed to grading systems in school, where a pass mark is 50 out of 100. It is appealing to think that cyber risk could be similarly quantified, scored, and benchmarked against peers. Doing so would help align board assessments, track progress, optimize security spending, and negotiate appropriate cyber insurance coverage.

There are tools and services that assess cybersecurity posture by simulating an external threat actor scanning for vulnerabilities. However, since organizations vary in industry, size, technology, risk treatment, and appetite, the self-determined passing mark should be taken with caution. Nonetheless, benchmarking against peers in the same industry provides valuable insights.

Know Your Probability of Being Hacked

When the board is satisfied with regular cybersecurity updates, existing mitigations, and business-as-usual operations, one critical question remains: What is the probability of being hacked in the next 12 months? Since perfect security is unattainable, a data-driven approach offers insight into the likelihood of a breach, potential attack vectors, and staff preparedness.

Simply put, the probability of a successful cyber breach is a function of attack vectors and defensive controls. For example, to model a takeover attack on an administrator account with privileged access, one must consider prevalent attack vectors such as social engineering, malware infections, and password spraying. Then, mitigating measures such as endpoint protection, two-factor authentication, and privileged account management must be factored in. Running simulations with repeated interactions can yield probabilities of an event occurring within a given timeframe. Nowadays, AI models can further refine risk assessments in complex environments with interdependent variables.

Conclusion

An effective board is not confined to governance and strategy. It plays a crucial role in fostering a collaborative environment where the cybersecurity chief and risk owners work together cohesively. It must be willing to challenge the status quo and trigger critical thinking. It drives a cultural shift, emphasizing that the best time to strengthen cybersecurity is during periods of stability, rather than waiting for a crisis. We must remain vigilant, ensuring cybersecurity always remains a priority.

Drills For Cybersecurity Fitness

Not just in personal finance, but also in cybersecurity, the phrase “making hay while the sun shines” holds true. Cyber threats are persistent but often remain concealed until they strike. In such unfortunate instances, the safeguards you expected to work have failed, and your secure coding checklist was not followed. To make matters worse, a standby service has failed to activate, and the log files for crucial insights of the attack have gone missing. Moreover, rumour-heard reporters kept reaching out to you for details. As an example, this episode could begin with a seemingly benign web defacement and escalate to a massive SQL Injection, compromising sensitive data, causing prolonged service outages, and leaving uncertainties about the timeline and sources of the attack, despite painstaking investigation.

Many companies invest heavily in cybersecurity but pay less attention to its ongoing operations. This is not by choice but due to prioritization constraints. Tech staff often face hectic schedules and long working hours. One moment, we are racing against time to meet project deadlines; the next, we are scrambling to recover from system outages. On quieter days, we conduct training sessions, attend sales pitches, experiment with emerging technologies, and endure the monotony of meetings. If any time remains, we work on procurement tenders, technical documentation, reports, and assist with recruitment. After getting home late, we clear urgent emails, get a few hours of rest, and repeat the routine the next day. As a result, aspects of cybersecurity that are not immediately pressing are often neglected. Over time, we let our guard down, allowing the busyness to take over our minds.

Just as regular exercise is essential for maintaining physical health, consistent drills are necessary to ensure cybersecurity fitness. These drills help confirm that all safeguards, processes, and alerts remain effective and operate as intended. Most importantly, they allow businesses, staff, users, and vendors to identify any missteps and validate assumptions made from the last review, and be ready for actions should crisis erupts.

Penetration Test

The idea behind a penetration test (Pentest) is to identify our own vulnerabilities before our adversaries do. The tools allow us to scan the entire network, mapping out hosts, operating systems, protocols, services, and versions in use, and critically uncover any shadow IT without our knowledge. With scripting, we can simulate common attacks like brute-force attempts on websites and databases. It can, also, check against a list of Common Vulnerabilities and Exposures (CVEs) such as SQL Injection and Cross-Site Scripting, etc., and alert us if our hosts were indeed vulnerable. Over time, the accomplished Pentest and its checklist could serve as a key performance indicator of the enterprise and to be tracked yearly.

Red Teaming

Unlike penetration testing that aims to uncover vulnerabilities, Red Teaming simulates a threat actor’s thought process to target specific assets, whether personal data, intellectual property, critical services, or privileged access for financial gain. This exercise tests various methods and pathways to bypass corporate defenses, evade surveillance systems, and exploit both system and human vulnerabilities within an organization, all while leaving no trace.

For example, understanding that remote reconnaissance might be blocked by corporate firewalls, the Red Team could exploit exposed remote access services to establish a covert foothold. This allows them to bypass perimeter defenses and advance the exploits further, such as harvesting login credentials and creating shadow accounts with elevated privileges to exfiltrate sensitive data. In another scenario, the Red Team might study the organization’s hierarchy, impersonating a procurement officer to submit fraudulent purchase orders to suppliers or posing as a newly hired senior executive to trick employees for financial gain.

From denial-of-service attacks to DLL sideloading, DNS poisoning, identity theft, ransomware, social engineering, spear phishing, and SQL injection, Red Teaming adapts its attack vectors to bypass specific defenses. As cyber threats evolve rapidly, it is advisable to engage external Red Team services, as these vendors bring a wealth of experience and up-to-date industry knowledge.

Phishing Drills

Phishing attacks are inexpensive to launch but highly effective. They exploit human emotions such as fear, greed, empathy, and curiosity. A single inadvertent click or screen touch can lead to disastrous consequences for an organization, and with finger-tip access to Generative AI and deepfakes, it has made it worse. While technology can provide some level of protection, regular drills and user education are far more effective in mitigating human error. But are there supporting data?

A well-designed phishing drill can help test several assumptions. First, does the relevance of the drill’s theme affect the likelihood of falling prey? For instance, general staff may be quick to click on an announcement about pay structures, while healthcare professionals might be more concerned with changes in patient care regulations. Second, do regular reminders from corporate leadership help reduce phishing click rates? Third, are employees who are subjected to regular drills less susceptible than those in a control group?

The results from previous drills I’ve experienced were encouraging. Staff members were particularly vulnerable to phishing emails related to organizational matters, with a 24% fall-prey rate compared to just 8% for other themes. The drills themselves were highly effective, reducing the click rate to 15% for those who received two rounds of practice, compared to 18% for the control group. However, management intervention, such as reminders from corporate leadership, did not significantly reduce the click rate.

That said, phishing drills aren’t without challenges. They can cause resentment, erode trust among staff, and may not even be effective, according to The Wall Street Journal reports from October 2023 and February 2025. Still, they remain a worthwhile exercise as they address the reality that individuals are often the weakest link in an organization’s security.

Table-Top Exercise

A cyber breach can cause far-reaching damage to an organization beyond just its infrastructure and systems. This includes business disruption, potential privacy violations, financial and reputational losses, legal claims, regulatory penalties, and more. With so much at stake, incident response should not be confined to the tech team alone but must also involve business partners and corporate leadership, including the heads of communications and legal.

In the event of a breach, time is of the essence. The tech team must sift through vast amounts of data and devices to identify the source of the attack and neutralize it. The situation can quickly become chaotic, with team members rushing into action from all directions, calling for additional resources, deciding on the best course of action, issuing public communications, and updating users and board executives, all while new findings and hypotheses continue to emerge.

Infrequent though they may be, cyber breaches can leave both tech and corporate leadership unprepared. Some team members may be unclear about their roles, while others could be distracted by irrelevant system issues. This is where a tabletop exercise becomes invaluable. By working through realistic scenarios, the interdisciplinary incident response team can familiarize themselves with their roles, actions, procedures, and responses in the event of a breach. Only when our response becomes as automatic as a muscle reflex can we contain an attack and minimize damage as quickly as possible.

Finally, with regular drills, we will be prepared to defend, recover quickly, and minimize losses in the event of a breach.


*Copyedit: ChatGPT