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From the Desk of a CISO – Leadership Lessons

Quite a bit has changed in information security since I began my career more than a decade ago. 

Talk of cloud being the primary enterprise development platform was based on complete speculation. Mobile computing had yet to hit full stride. Software as a service (SaaS) was in its infancy. Since then, we have seen the rise of the nation-state attacker, extensive malware attacks, highly-publicized insider threat cases, exponential growth of data due to the declining costs of storage and considerable digital transformation investments. As all of these trends evolved and took hold, the nature of information security also changed.

Throughout all of these changes, I have worked in information security; previously, at a national retail enterprise and, more recently, as a CISO here at Code42. Over the years, I’ve learned a few important lessons about how to be successful in information security that I’d like to share here.

Lesson 1 – Be Part of the Solution

Too often security teams do a great job at identifying and pointing out risks and then handing them off to others to solve. In their earnest desire to eliminate those risks, they forget how important it is to understand how people go about getting their work done. So, rather than try to help others deliver their work or projects in a secure way, they identify risks and throw them over the fence for other teams to fix. That has to stop. We need to create partnerships, build empathy and become part of the solution. Building empathy helps us understand how others deliver work and the struggles they might go through to get their jobs done.

Because we are developing software at Code42, our top risks lie in the software development cycle. That’s why my team works very closely with our developers to help identify and address security gaps. To build greater empathy, I have challenged my team to learn the basics of a coding language. This has helped us gain a fuller understanding of the challenges developers face everyday and, more importantly, how we need to work with them to be part of the solution.

Lesson 2 – Balance Risk

In security, it is less about eliminating risks— and more about balancing risks. Think of a retail floor. Sure, everything on a shelf that isn’t locked down is at risk of being stolen. But if you lock everything up behind glass, your sales are going to plummet. At the end of the day, you are in the business of selling goods, which is why retailers don’t lock up everything. It’s the same with all business risks. You have to balance the business benefit with the business risk and put reasonable risk mitigations in place. For a retailer, this could be cameras, security guards, and/or only locking down items with a high risk of theft.

As a security leader, we don’t want to place overly aggressive security controls on everything. We are trying to tune the right level of security for the organization. You have to balance what the board, CEO and customers want and, at the same time, match the culture of the organization.

In a lot of cases, security leaders push forward with their own security risk posture ideals versus trying to truly understand the acceptable risk posture of the organization.

Lesson 3 – Build a Strong Team

While a bit more obvious, I can’t stress enough the importance of building and retaining a strong team. The team here at Code42 is close-knit. I have worked with many of these people for more than a decade. It’s hard to place a value on that. It’s a lot like professional athletes who know the moves their teammates are going to make before they do. That makes it possible to build a well-tuned, committed and effective team, not to mention retain talent in a talent-deficit industry. When you have a team you trust, it makes security much more effective and laser focused on the overall mission of the organization. I am thankful to be a part of such a strong, dedicated team that trusts one another and has a high degree of respect for one another. 

Lesson 4 – Transparency Trumps

To be effective in this industry, security professionals need to be transparent. In some cases, security teams still operate like the man behind the curtain: No one knows what magic they are operating, and  budget is gained by claiming that the sky is falling. But with today’s skepticism, seeing is believing. That’s why it’s so important to demonstrate how risks could be exploited. I recommend having your red team perform an exercise to determine exactly how easily a risk may be exploited, and share the results with other decision makers. 

In the same vein of transparency, it’s important to explain risks as they really are. Many security professionals will overhype a risk in an attempt to get attention or budget for a project. That tack may work in the short-term, but it will diminish trust in the long run.

As a security team, we are 100% transparent on the risks we see and the areas where we are digging deeper. This way, when a threat or new risk arises, we have a tremendous amount of trust and support to mitigate the risk. 

Lesson 5 – Provide Value, Don’t Fear Failure

Finally, being a CISO, or data security professional in general, is a stressful job. There is a lot of discussion around stress in the information security profession and how, as a result, the average tenure for CISOs is about two years or less. CISOs must balance the stress by focusing on the good, which is the value they’re providing to their business. At Code42, we strive for a blameless culture – one where we learn lessons rather than fear failure. This type of a culture helps contextualize stress. 

In my job, I want to feel challenged throughout the workday. I’m energized and get a lot of joy knowing that we are providing value and actually helping our company and customers address their security risks. We are working for a company that helps all of our customers deliver on security with the software we develop. For a security professional, it doesn’t get more exciting than that.

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