Cybersecurity isn’t really about firewalls or encryption. It’s about people.
And the uncomfortable truth is that hackers—whether sophisticated nation-state actors or opportunistic phishers—understand human nature far better than most corporate leaders ever have. They exploit curiosity, urgency, trust, ego, and fear. Meanwhile, too many executives still believe cybersecurity is just a technical problem that IT can “patch.”
The psychology behind the breach
When I was at Red Sift and Valimail, we watched attacks evolve not because the technology changed first, but because attackers’ understanding of people did. Social engineering—phishing, pretexting, business-email compromise—still accounts for the majority of successful intrusions. According to the U.S. Cybersecurity & Infrastructure Security Agency (CISA), over 90 % of successful cyber incidents begin with a human-enabled action, such as clicking a malicious link or misconfiguring access rights (CISA Annual Report 2023).
Hackers don’t brute-force systems anymore; they brute-force psychology. They study how employees communicate, how leadership pressures teams for speed, and how routine creates complacency. They mimic your vendors, your CEO’s writing style, your invoicing cadence. In short, they don’t just hack code—they hack context.
Why leadership culture creates opportunity
Here’s the part most leaders miss: every successful breach tells a story not only of technical failure but of organizational behavior.
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Speed over security: When management celebrates instant replies and “always-on” responsiveness, employees hesitate to verify suspicious messages.
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Complex processes: Lengthy password resets or clunky VPN logins lead people to find workarounds.
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Low psychological safety: If people fear punishment for mistakes, they hide incidents—giving attackers more time to exploit them.
The 2023 Verizon Data Breach Investigations Report found that 74 % of breaches involved a human element—errors, misuse, or social engineering. That statistic hasn’t budged much in years, even as security spending soars. Clearly, technology isn’t the limiting factor. Human nature is.
How hackers harness empathy and narrative
Successful attackers are, ironically, great storytellers. They craft believable micro-narratives—an unpaid invoice, a shipping delay, an urgent HR message. They use empathy as a weapon: “I’m just trying to help you solve this problem quickly.” That small emotional bridge is all they need.
At Red Sift, one of our simulated phishing tests exploited compassion. We sent employees a fake email titled “Help our colleague in crisis” with a donation link. Click rates spiked to 68 %. No exploit kit, no malware—just empathy used as leverage.
Turning awareness into resilience
So what should leaders do differently? Here’s what I’ve learned from leading go-to-market teams in cybersecurity companies:
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Model security behavior at the top
If the CEO still reuses passwords or ignores MFA prompts, every awareness campaign will fail. Leadership’s daily habits set the baseline for cultural norms. -
Design for frictionless security
Security that slows work will be bypassed. Invest in identity automation, passwordless systems, and secure-by-default workflows. At Valimail, we saw adoption soar when email authentication required zero user action—security became invisible. -
Shift from compliance to culture
Annual training slides don’t change habits. Storytelling does. Share anonymized internal “near-miss” incidents. Make security personal, not procedural. -
Reward reporting, not silence
Celebrate the employee who reports a phishing attempt, even if they clicked first. Fear kills disclosure; disclosure saves the network. -
Fuse cybersecurity with leadership training
Managers must understand behavioral risk as deeply as financial risk. Cyber awareness isn’t IT literacy—it’s emotional intelligence under pressure.
What organizations like Hallmark and CareFortis reveal
Healthcare is a perfect test case. Hallmark and CareFortis operate in environments where lives—not just data—are at stake. Both have invested in training clinicians and administrators to recognize social-engineering cues. Yet, they also learned that stress, fatigue, and urgency—common in healthcare—make staff more susceptible to manipulation.
According to the U.S. Department of Health and Human Services (HHS) Office for Civil Rights, healthcare breaches rose 93 % between 2018 and 2023, with an average cost per incident exceeding $10 million (HIPAA Journal 2024). The biggest driver? Human error. That’s not just an IT problem; it’s an organizational empathy gap.
The leadership lesson
Hackers understand that the shortest path to your data runs through your people. They study incentive structures, communication tone, and cultural blind spots. Leaders who ignore these soft factors are, unintentionally, on the hacker’s side.
True cybersecurity leadership starts with humility—accepting that people, not systems, are the front line. It demands curiosity about human behavior, not just technical architecture. It means building cultures where trust and vigilance coexist.
Hackers already know that every organization is only as secure as its most distracted moment. The question is: do your leaders know it too?
