The Human Factor in Cybersecurity: Dewayne Hart on What CTOs Overlook

Dewayne Hart is a leading cybersecurity speaker and thought leader, with two decades of service in the United States Navy and a career dedicated to protecting organizations against evolving digital threats.

Combining his experience in military intelligence, enterprise cybersecurity, and business leadership, Hart has become a trusted voice in building security-minded cultures. Additionally, as a technology speaker, author, podcast host, and business leader, he translates complex cyber challenges into practical insights, closing organizational blind spots.

Dewayne Hart’s insights remind us that cybersecurity is as much about human behavior as it is about technology.

Awareness, culture, and personal responsibility are crucial to mitigating risk and staying ahead of emerging threats. His advice is clear: empower your people, invest in the right tools, and never underestimate the human element in cybersecurity.

In this exclusive conversation, Hart shares his journey from the Navy to the forefront of cybersecurity, why humans are often the weakest link, and how organizations can stay resilient in a world of rapidly evolving digital threats.

Dewayne, thank you for joining us today. You spent two decades in the Navy before stepping into cybersecurity. That’s quite a transition! How did your military experience shape your approach to this field?

Dewayne Hart: Well, you know, I used to sail the ocean for 20 years. I was in the United States Navy. And while in uniform, I was heavily involved with technology and some of the other types of industries with Intel.

After retiring from the military, I earned a master’s degree in information assurance, a valuable credential. Then I said to myself, ‘I want to work in the world of cybersecurity.’

So, I started working in cybersecurity. But, I wasn’t really pushed to take it seriously until one day a friend of mine came on the job with a CISSP book. I looked at it and I read it. I said, you know, that really interests me.

So, I studied for the CISSP, and I earned my certification. And after that, I began traveling throughout the industry to write books, and I also wrote for Forbes, hosted podcasts, and gave talks.

Then, after that, it just occurred to me that, hey, you like cybersecurity. Okay. So, I said to myself, ‘I’m going to excel in cybersecurity and in what I do.’ That’s how my industry began, and that’s how I became a cybersecurity speaker, writer, author, and business owner today.

That’s quite impressive. Many organizations still operate in a reactive mode when it comes to cybersecurity. From your perspective, what should leaders be doing proactively to protect their companies?

Hart: Okay, I always say that number one, as a business, you need to build a security-minded culture. That means your employees and staff need to buy into cybersecurity. All too often, organizations operate in a reactive mode and wonder why they’re experiencing cyberattacks. You need to examine your culture and ensure that people have a buy-in.

The second way is that leaders themselves need to understand the security capabilities. What is it that you can and cannot achieve when it comes to cybersecurity? Because you don’t want to get caught in a cyber-attack and realize that you cannot defend your enterprise. Much of that goes into your detection engineering program. Can you detect where you’re most vulnerable?

I often make the statement that one of the things that damages organizations is when they have these unknowns, and these unknowns are referred to as blind spots. That’s similar to driving down the highway and not seeing that vehicle on your left side. That is your blind spot. Therefore, organizations must have a clear understanding of their security capabilities and potential blind spots.

Additionally, from a business perspective, you must ensure that you are investing in the right products and services. Often, organizations purchase tools that do not deliver the value they should. Then they realize that they’ve paid three or maybe four million dollars for these tools, and they don’t use them. So, I’ve always said that if you’re going to be proactive, focus on your culture, focus on the technologies, make sure you have a high level of visibility, and also, from the business side, invest properly.

The phrase “humans are the weakest link in cybersecurity” is often used. From your experience, what’s really behind this vulnerability?

Hart: You know, I hear that question a lot, and it is humans, but I’m going to take it to the next level. I think it’s a lack of awareness. One of the things I have learned about the security industry is that humans are non-standard, while technologies are standardized.

That means technologies will operate as intended. But humans have a choice. They can either follow protocols or they cannot follow protocols.

So, what we have to do is ensure that when we teach these cyber-awareness courses, we teach individuals to act upon the knowledge, because cyber-awareness is not just about being aware of cybersecurity.

But what if I take it to the next level and tell individuals that they need to act upon the knowledge? That is the main problem I see in this area of cybersecurity, because humans are the weakest link. But likewise, if we have a security-minded culture, we can remediate that issue.

I’ve always said that if my audience were in the left lane and a hacker were in the right lane, I want my audience to reach the finish line before the hacker. However, to get there, my audience needs to understand how cybersecurity works.

Because, as of now, there’s this place of fear, and every time someone hears the word cybersecurity, they feel fear. And so, what happens is they see somebody like me, and they start to hide their mobile phones. No, cybersecurity is here to protect you, but what you have to do is follow protocol.

What I focus on is discussing the roadmap for cybersecurity, emphasizing its value, and highlighting individual responsibility.

Dewayne, thank you so much for taking the time to share your expertise today. As we wrap up, what’s the one piece of advice you’d give to individuals and organizations looking to stay ahead in cybersecurity?

Hart: What is it that you, as a person in my audience, are supposed to do with cybersecurity, right? Because everyone is held responsible. Anyone who touches a system, regardless of whether you’re a business leader, a journalist, a teacher, or a doctor, is held accountable.

So, when you come in and hear a cybersecurity talk, I want you to leave there with your fears gone, and I want you to be able to approach cybersecurity with a clear mindset.