Critical Errors in Cybersecurity Leadership


Leadership & Executive Communication
Training & Security Leadership

Zero Trust Expert Chase Cunningham on His Latest Book About Leadership Styles

Chase Cunningham, advisory board member, Akeyless

Chase Cunningham, aka the Doctor of Zero Trust, has written a new book, “How NOT to Lead: Lessons Every Manager Can Learn from Dumpster Chickens, Mushroom Farmers, and Other Office Offenders,” which details critical errors that can undermine your cybersecurity leadership and jeopardize your reputation and your company’s future.

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Expressing disappointment over the lack of accurate technology books on leadership, Cunningham said that many individuals reach leadership positions through “fortuitous circumstances and luck” rather than merit. “Where’s the book on how not to be that person nobody wants to work for? Because, Lord knows, I’ve worked with plenty of them,” he said.

Cunningham discussed the tendency for executives to lose touch with their roots as they climb the corporate ladder and potentially treat subordinates poorly. He shared a personal crisis of conscience he experienced upon entering the C-suite that shows the importance of staying grounded and empathetic.

“The goal is often to move into the C-suite, but a lot of times what happens is you forget where you came from. You wind up treating people the way you wouldn’t want to be treated when you were there doing the work,” he said.

Cunningham challenged the prevailing notion of rapid development in technology being required. He advises leaders to understand strategic goals and carefully navigate processes to achieve quicker, better and more effective outcomes.

“Slow is smooth, and smooth is fast,” he said. “That’s a motto everyone should adopt. If we really took the time and understood the strategic things we’re trying to do and massaged that process, we can do it quicker, better, faster by actually being slow, which is kind of a weird thing to wrap your head around. But it does make a heck of a difference.”

In this video interview with Information Security Media Group, Cunningham discussed:

  • Critical errors and pitfalls that can jeopardize cybersecurity management;
  • Challenges that can contribute to ineffective leadership;

  • How to achieve quicker and more effective outcomes in your career.

Cunningham, aka the Doctor of Zero Trust, is an advisory board member of Akeyless. Prior to Akeyless, he was the chief strategy officer at Ericom Software, where he shaped the company’s strategic vision, road map and key partnerships. He also served as vice president and principal analyst at Forrester Research, providing strategic guidance on zero trust, artificial intelligence, machine learning and security architecture design for security leaders worldwide.


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