Security, risk, and control assessments are typically done for the sake of compliance: tools deployed, audits passed, workflows completed, boxes checked. That’s no longer enough for boards, customers, and regulators, who all want an answer to a harder question: ‘can you prove your controls are working right now?’
I often ask CISOs a version of that question, and the honest answer is usually some form of “we think so.” It’s not because they’re careless. Most control checks still happen the way a dentist visit does. When your dentist asks whether you brush and floss every day, you could fib and say yes, but one look at your x-ray tells the real story.
Security works the same way. An annual audit captures what you told the auditor, or what looked true on the day someone checked. But it may not be the ground truth.
There’s a gap between what we believe about our controls and what we can actually verify. That’s where the trouble lives, and it is wider than most teams admit. In a 2025 Dell study, 69 percent of IT professionals said their own leadership overestimates the organization’s readiness for a cyber event. Even the people closest to the controls think the people reporting on them upstairs are too confident. Without live control evidence, no one can check the belief.
Why point-in-time proof keeps failing
A control is not a monument. It is a living thing that drifts. A firewall port opened for a two-week integration may still be open eight months later. A vendor that passed review last year changes a configuration this year. A new system goes live between audit windows. Something can drift out of place the day after an audit closes and stay that way for months, and the only honest thing a CISO can say about it is that the last review looked fine.
You can’t rely on sampling-based assessments
Enterprises are constantly changing with digital transformation. New AI risks are stacking on top of existing IT risks, and the enterprise landscape itself grows by double digits every year.