Why Cybersecurity Leaders Need First-Hand Experience to Truly Lead

When it comes to cybersecurity, it’s easy to think the job is just about stopping hackers or keeping networks safe. But effective cybersecurity leadership goes much deeper. It’s not just about understanding firewalls and encryption; it’s about understanding people, their struggles, and how technology fits into their daily work. To lead well, a cybersecurity leader must have lived experience—a phenomenological understanding—of what it feels like to work at different levels of an organization.

Here’s why that matters.

Cybersecurity Isn’t Just Technical—It’s Human

Imagine you’re a teacher in a school. Your focus is on helping students, not on remembering complex passwords or following strict data policies. Now, imagine a cybersecurity leader tells you to change your password every month or introduces a system that slows you down. Without understanding how those changes affect you, that leader might create frustration and even resistance.

This happens because cybersecurity leaders often focus on policies and systems without considering the human experience. But the truth is, cybersecurity is just as much about people as it is about technology. When leaders don’t experience the day-to-day challenges of their employees, they miss out on valuable insights that could make policies both effective and user-friendly.

Phenomenology: Seeing Through Others’ Eyes

Phenomenology is a big word, but its meaning is simple: It’s about understanding what something feels like from another person’s perspective. For a cybersecurity leader, this means asking questions like:

  • What is it like for a teacher to navigate the school's online grading system?

  • How does a finance employee feel when they’re asked to report a phishing email?

  • What challenges do IT staff face when balancing security updates and daily tech support?

Leaders who take the time to step into these roles—whether by shadowing, listening, or even performing those tasks themselves—can better understand how their decisions impact others. This kind of first-hand experience is critical for creating policies and solutions that work in the real world.

Layers of Experience Matter

To truly lead, cybersecurity professionals must go beyond their own technical bubble. Here’s why:

  1. Understanding Non-Technical Roles
    A cybersecurity leader should understand how security policies affect non-technical staff. For example, a teacher juggling lesson plans and classroom management may struggle with overly strict password rules. A good leader would balance security needs with practical, user-friendly solutions.

  2. Bridging the Gap with IT Teams
    IT staff live on the front lines of technology. They handle updates, troubleshoot problems, and face the brunt of user frustration. Leaders who work closely with IT teams—by spending time in their shoes—can develop solutions that make their jobs easier instead of harder.

  3. Seeing the Bigger Picture
    Beyond the day-to-day, cybersecurity leaders need to understand how security ties into the organization’s overall mission. In schools, this might mean ensuring student data is safe while enabling teachers to focus on education. In businesses, it might mean protecting customer information while supporting productivity.

Why Lived Experience Builds Trust

When leaders understand the lived experiences of their teams, they build trust. Employees are more likely to follow cybersecurity policies if they know their leaders “get it.” Instead of feeling like security is just another obstacle, they see it as a shared responsibility.

Leaders with hands-on experience can also communicate better. Instead of using jargon, they can explain cybersecurity concepts in ways that make sense to everyone. This not only improves compliance but also fosters a culture where people feel empowered to ask questions and report concerns.

How to Gain First-Hand Experience

If you’re a cybersecurity leader—or aspiring to be one—here are some practical steps to build your phenomenological understanding:

  • Shadow Different Roles: Spend a day working alongside teachers, office staff, or IT technicians.

  • Listen Actively: Host listening sessions to hear directly from employees about their cybersecurity challenges.

  • Test Your Policies: Try following your own security policies. Are they practical and easy to understand?

  • Keep Learning: Technology and workflows are always changing. Stay curious and adapt to new challenges.

The Takeaway

Cybersecurity leadership isn’t just about expertise; it’s about empathy. A leader who has experienced the day-to-day challenges of their team is better equipped to make decisions that work for everyone. By stepping into the shoes of others, leaders can create security solutions that protect the organization without disrupting its mission.

Whether you’re protecting a school or a business, remember: great cybersecurity leadership starts with understanding the people you serve.

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