Cybersecurity doesn't fail in the SOC—it fails in silence, right before the regulator shows up, the headlines break, or the CEO quietly exits.
Consider this: In August 2025, the media publicized a sweeping hack of the federal judiciary’s case-filing system that exploited unresolved security holes discovered five years prior, allowing hacking groups to steal reams of sensitive court data in the ongoing breach. These glaring vulnerabilities included lack of multi-factor authentication and delayed upgrade of critical infrastructure despite systemic exposure. This incident, however, is just the tip of the iceberg; the internet is awash with debilitating data breaches whose roots can be traced back to executive apathy and lax governance structures.
In the next section, I will share three penetrating questions executives must ask to uncover their critical blind spots and boost cyber resilience.
The Three Questions
Over the past 15 years managing IT and security teams, I have learned that executives don't need more frameworks on paper. They need blunt questions—and a practical playbook for turning answers into action.
1. When Did You Last Feel the Heat of a Cyber Crisis?
A quarterly “update” replaces long, winding slides for a live breach drill. No charts—just decisions. Within minutes, leaders discuss potential implications of unplanned shutdowns, regulatory disclosures and reputational fallout. Cyber risk ceases being an IT topic and becomes a vital leadership test.
This was Sapan Talwar’s approach at Perfetti Van Melle: Crisis Cyber Tabletop Exercises (CCTE) with no theory—only hard choices. “The CCTE not only raised awareness but also equipped our executives with the knowledge and confidence to make informed decisions in the face of cyber threats.”
Executives who’ve felt breach chaos coordinate faster across IT, legal, ops and communications—and make better calls when seconds matter. Here are three ways to make this happen:
- Run quarterly executive tabletop drills to put decision-makers under realistic pressure and improve crisis decision-making quality and speed.
- Decide on real trade-offs in the room, document those choices, and assign follow-up actions with clear executive owners to drive accountability.
- Close critical gaps within set timeframes and retest to confirm resilience before the next incident.
But crisis readiness is only one part of resilience. Clarity of roles matters just as much.
2. Can Teams Describe Their Security Role Clearly?
At one mid-sized firm, the marketing team shipped hundreds of thousands of client records to a third party via a zipped file to kick-start a marketing campaign, with zero consideration for the security implications. The procurement team, on the other hand, onboarded a poorly vetted supplier, citing schedule and budget overruns. Both gaps were significant enough for a breach to slip through. No one was sanctioned for this appalling behavior.
This is how executive silence filters down to the front lines. Employees may attend annual training yet fail to recognize the connection between security and their daily work. One careless click or weak password can result in millions of dollars in wasted technology spending. This is where culture either dies in PowerPoint or becomes your strongest firewall. Here are four ways to mitigate this risk:
- Launch quarterly “cyber scope conversations” in every business unit — structured 60-minute sessions where leaders and key staff review current cyber risks, clarify roles and responsibilities, surface misunderstandings, and agree on concrete actions to close ownership or accountability gaps.
- Map the answers into a simple matrix showing who owns which risks and where handoffs occur. For example:
- Customer service owns password resets, while IT owns the authentication platform.
- Finance approves vendor payments, while procurement manages third-party risk checks.
- Keep learning alive with short, gamified sessions — run monthly phishing quizzes, scenario-based challenges, or live cyber drills that mimic real-world threats, reinforcing key behaviors and building team muscle memory under realistic conditions.
- Link every lesson back to business survival to reinforce that, with nearly 60% of breaches tied to human error, clarity of roles is the first line of defense.
Even with clear roles, resilience falters if the board treats cyber as an afterthought.
3. Does Your Board Fully Grasp Its Cybersecurity Role?
In some boardrooms, cyber updates sound more like weather forecasts—predicting storms after they’ve already passed. Directors receive filtered reports, often stripped of urgency, while threats build quietly out of view. Without direct CISO access, critical insights are lost in translation, and the board is left making decisions in the dark.
Boards that lead from the front treat cyber oversight as a core governance duty, not a quarterly formality. They establish direct reporting lines, enabling the CISO to communicate directly with the board or audit committee without the need for intermediaries. They replace generic posture updates with scenario-driven discussions: “What if our largest vendor was breached tomorrow?” They establish decision authority before the crisis—who can shut down systems, approve disclosures, or call regulators—and measure governance metrics such as board cyber literacy, incident response speed and compliance readiness.
The payoff is measurable. Harvard Law School’s 2022 analysis of 4,000 companies worldwide found that organizations with dedicated board-level cybersecurity oversight committees achieved significantly higher security ratings and up to four times greater shareholder value than those without such oversight.
The cost of neglect is just as clear. In 2023, genetic-testing company 23andMe suffered a credential-stuffing attack that exposed data from nearly 7 million customers, including sensitive ancestry details. Initial disclosures downplayed the scale, but later filings revealed roughly half its customer base had been affected. Within months, all seven independent directors resigned, governance collapsed, and by March 2025, the company filed for bankruptcy, with its CEO stepping down. When boards treat cybersecurity as an afterthought, the damage extends beyond reputation—it can dismantle leadership and threaten survival.
Here is a four-step process to mitigate this gap:
- Establish direct CISO-to-board reporting. Remove informational filters and improve decision quality.
- Form a streamlined, executive-led cyber risk governance committee with the CEO, CFO, COO, and General Counsel to share accountability.
- Define breach decision authority in advance to prevent paralysis during high-impact events.
- Implement a concise, business-focused cyber scorecard tracking the coverage of non-negotiable controls across your crown jewels.
Because you can’t govern what you don’t understand—and you can’t lead what you don’t practice.
Leadership Is the Ultimate Control Layer
Cybersecurity doesn't fail because of tools—it fails in silence. Leaders who avoid hard conversations leave gaps no firewall can close. These questions aren't theory—they're a mirror to leadership courage. Start asking them at your next executive meeting—and keep asking until silence disappears. Real resilience begins when leaders choose honesty over comfort.
