Beyond Cyber Awareness Month: What Leaders Must Do Year-Round to Prepare for the Next Cyber Crisis

A Wake-Up Call from the Real World 

Imagine this: it’s a crisp Tuesday morning, the board has just wrapped up a quarterly strategy review, and the CEO is preparing for media interviews about a new product launch. Suddenly, phones start buzzing. The company’s systems have been locked by ransomware. Files are encrypted, customers are locked out of their accounts, and a “pay up or lose everything” message flashes across screens worldwide. 

In that moment, awareness campaigns and posters about “cyber hygiene” don’t matter. What matters is whether leadership has rehearsed this moment—who speaks, who decides, and how fast the organization can act. Sadly, too many companies only think about this in October, during Cybersecurity Awareness Month, and not as part of their year-round resilience strategy. 

Why Cyber Preparedness for Leaders Matters Now 

The cyber threat landscape is intensifying, and it’s hitting the boardroom just as much as the server room. According to IBM’s Cost of a Data Breach Report 2023, the global average cost of a breach hit $4.45 million—a 15% increase over three years. Even more telling, 51% of organizations plan to increase security investments specifically because of these rising costs. Leadership isn’t just a stakeholder in cyber incidents, it’s a driver of resilience, reputation, and recovery. 

Executives often assume cybersecurity is a “technical problem.” But look at Clorox, which suffered a cyberattack in August 2023. The disruption slowed down production and order processing for weeks, forcing the company to revert to manual operations. The result? Widespread product shortages and a projected financial hit of over $350 million. That kind of impact shows cyber risk is not just about IT, it’s about operational resilience, financial stability, and leadership accountability.

Related: When the Machine Thinks for Itself: Preparing Executives for Rogue AI Crises

The Common Concerns Leaders Raise 

When I sit with executive teams, three questions come up again: 

1. “Isn’t this just an IT issue?” 
   No. IT fixes systems. Leadership manages the crisis: deciding on ransom payments, stakeholder communications, regulatory disclosures, and reputational fallout. 

2. “How do we prepare without overwhelming the board?” 
   You don’t need to turn directors into cybersecurity experts. Instead, you need to build muscle memory around decision-making during a cyber crisis. 

3. “What’s the return on all this preparation?” 
   Preparedness reduces the duration and impact of an incident. A faster recovery means less downtime, lower costs, and more trust from customers and regulators. 

What Leaders Should Be Doing Beyond October 

1. Move from Awareness to Action 

Cybersecurity Awareness Month is valuable—it gets employees talking about phishing and password security. But leaders can’t stop there. Executives must integrate cyber preparedness into corporate risk management. That means regular tabletop exercises, updating crisis communication plans, and linking cyber resilience to business strategy. 

Think of October as a fire drill. Helpful, yes—but useless if the sprinklers don’t work or the evacuation plan is outdated. 

2. Practice Leadership Under Pressure 

Tabletop exercises aren’t about memorizing technical details. They’re about decision-making when information is incomplete, emotions run high, and the clock is ticking. 

In the aftermath of the 2024 Change Healthcare ransomware attack, one of the biggest challenges wasn’t just restoring systems—it was how leadership communicated with investors and regulators under extreme pressure. Delays and uncertainty around disclosures drew heavy scrutiny and rattled market confidence. The lesson? Even seasoned executives need rehearsal when it comes to cyber crises. Practicing those conversations in a simulation is far better than stumbling in front of shareholders or the press. 

3. Communicate with Confidence 

During a cyber crisis, silence is deadly. Customers, employees, regulators, and the media will all demand answers. Leaders must be ready to explain what happened, what’s being done, and why stakeholders should trust them. 

Common mistake? Over-promising. In the rush to reassure, leaders often say, “We’ll be back online in 24 hours”—only to fail publicly. A better approach: commit to transparency and regular updates while acknowledging uncertainty. 

4. Learn from the “Ignore vs. Prepare” Divide 

Ignore Case – Sony Pictures (2014): 

When Sony Pictures was hacked, attackers leaked troves of sensitive emails, unreleased films, and employee data. The breach was devastating on a technical level, but it was leadership’s handling of the crisis that made headlines. Executives scrambled to explain what had happened, messaging to staff and the public was inconsistent, and leaked internal correspondence damaged reputations at the highest levels. Sony became a case study in how not rehearsing crisis leadership—especially around communications—can intensify the damage far beyond the IT department. 

Prepare Case – Maersk (2017, NotPetya): 

When the NotPetya attack struck, Maersk’s global shipping operations ground to a halt. But leadership had rehearsed crisis coordination and continuity planning. Executives quickly established priorities, activated business continuity measures, and partnered with external experts, including Microsoft, to restore critical systems. Within ten days, operations were largely back online. While losses exceeded $300 million, Maersk’s transparency and decisive leadership became a case study in resilience and crisis communication done well. 

Preparation didn’t prevent the breach—but it prevented a crisis of confidence. 

5. Build Year-Round Cyber Resilience Habits 

Cyber resilience is like fitness. You can’t go to the gym for one month a year and expect results. Leaders should embed cyber preparedness into their annual calendars: 

• Quarterly: Run short executive-level tabletop exercises. 
• Biannually: Review and update crisis communications and disclosure protocols. 
• Annually: Benchmark resilience maturity with independent assessments. 
• Ongoing: Align cyber preparedness with enterprise risk and business continuity strategies. 

Mini Section: A Common Mistake to Avoid 

Too many boards rely solely on dashboards or heat maps to track cyber risk. While helpful, those visuals don’t test decision-making. It’s like looking at a weather forecast but never practicing what to do when the storm hits. 

Practical Checklist: Leadership Cyber Readiness 

Here are five steps you can start today: 

• Schedule a cyber tabletop for your next board or leadership offsite. 
• Identify your “crown jewel” systems—the ones that, if compromised, could cripple operations. 
• Clarify decision authority for ransom payments, public statements, and regulatory disclosures. 
• Update your crisis comms plan with cyber-specific scenarios and stakeholder messaging. 
• Benchmark your program with an external assessment to uncover blind spots. 

Closing Thoughts: From Awareness to Assurance 

Cybersecurity Awareness Month is a great catalyst. But true resilience comes when leaders treat cyber crises as inevitable and prepare accordingly—not just in October, but every month of the year. 

The companies that thrive after cyber incidents aren’t the ones with the best firewalls. They’re the ones whose leaders are ready to step into the spotlight, make tough calls, and steer the organization through chaos. 

If you’re looking to strengthen your team’s preparedness, PreparedEx has helped Fortune 500s and global brands rehearse these exact moments. Reach out to explore how we can help your leadership team move beyond awareness into year-round resilience.