What Every Business Leader Should Know Before Their First Cybersecurity Assessment

From our Virtual Chief of Security

When I sit down with business leaders preparing for their first cybersecurity assessment, I often see the same concern: they think this is just an IT conversation. It’s not. A successful security assessment depends far more on leadership and communication than it does on technology.

After years of guiding organizations through this process, I’ve learned that the companies who get real value from security assessments understand a few fundamental truths going in. Here’s what I wish every business leader knew before we start.

1. This conversation belongs to everyone, not just IT

Your first instinct might be to hand this off to your IT person or security manager. I understand why—they speak the technical language. But here’s what I’ve learned: the most successful assessments happen when I’m talking to the people who are actually operating the business.

That means the CEO or president, the office manager, the HR person, and yes, generally a bit of IT. Why? Because security touches every part of your operation. The office manager knows how invoices are processed. HR knows how employee data is handled. The CEO understands the strategic risks that keep them up at night.

If we limited the conversation to just IT, we’d miss critical context about how your business actually works. And that context is everything.

2. We'll spend more time talking about people than technology

This surprises most business leaders. They expect me to immediately dive into firewalls, encryption, and software patches. We’ll get there, but that’s not where we start.

The reality is that we spend far more time talking about your people, your processes, and your organizational culture than we do about IT infrastructure. I’m looking for whether there’s a general consensus of security priority within your organization. I’m asking how the business goes about recovering from incidents and disasters—not just from an IT backup perspective, but from a business continuity standpoint.

I need to understand how everyone in your organization approaches security, because technology alone can’t protect you if your people and processes aren’t aligned.

3. Your baseline matters more than your solutions

No one ever gets the outcome they think they’re going to get from a security assessment. I don’t mean that in a negative way—I mean that scores and checklists aren’t the point.

In an initial assessment, those scores are really only indicative of where one department is performing compared to another, or how any business is performing compared to any other business. But here’s the important part: that baseline gives us a point of reference to say “this is where we are today” and “this is where we want to be.”

We spend far more time talking about solutions than we do about scoring our way through some checklist. The assessment isn’t the destination—it’s the starting point for meaningful improvement.

4. Leadership drives success, not just compliance

The success of your assessment is going to depend on leadership. It’s not about the security person or the office manager I work with on a regular basis. It’s really about getting a lot of cross-departmental communication happening between your teams.

Nobody does well on a security assessment the first time through. There are often some shocked responses when we go through initial results. But I don’t score assessments based on how quickly teams work together or how much things can improve. I score based on how things are right now—because how else will we know where to start with remediation?

What makes the difference? Leadership that prioritizes security, encourages collaboration, and is willing to have honest conversations about gaps.

5. Preparation is a myth—and that's okay

Here’s a truth that might relieve some pressure: nobody is really prepared. Nobody is really prepared with what they would need for a standard security assessment the first time through.

Yes, we often look for detailed documentation during assessments, and yes, many organizations do extensive reviews beforehand. But technology performs about as well as your people are performing, because your people are really your first line of defense.

So we spend very little time talking about tools and technologies during initial assessments. Instead, we focus on people, training, collaboration, and making sure that what is spoken about is understood and what is directed is actually followed through.

Where Real Security Begins

When we spend very little time talking about technology and far more time talking about people, training, and collaboration, that’s when real security improvement happens. The assessment itself is just the beginning of an ongoing conversation about how to protect what matters most to your business.

If you’re preparing for your first security assessment, take a breath. You don’t need to have all the answers. You need to be ready to have honest conversations, bring the right people to the table, and commit to the work that comes after we establish that baseline.

That’s where mature security really begins.

Angela Hogaboom is the Chief Information Security Officer at RSI, where she helps organizations build security programs that work with their business, not against it.