There's no single "right" method. Most businesses end up using two or three together.
Self-assessment against a framework
You run it yourself, using an established standard as the yardstick. For example:
This approach is inexpensive, repeatable, and good for building a baseline.
The catch is blind spots. You'll measure what you already know to look at, which means the gaps you don't know about tend to stay hidden.
Third-party assessment
An outside team reviews your environment and reports back. You get:
It's also point-in-time and it costs money, so most businesses do this annually or when something significant changes.
Automated posture management
Software continuously watches configurations, patch levels, agent health, and control coverage, then flags drift as it happens. This is where endpoint posture management and ESPM tools help support.
The strength is speed and coverage. The common failure is lack of remediations. If you get hundreds of findings, but no practical next steps, your team could end up ignoring the dashboard entirely.
Penetration testing and adversary simulation
A tester tries to break in and then tells you what worked. This validates your posture rather than just describing it, and it surfaces chained weaknesses that a mere checklist would score as low risk its own.
It's the most expensive and disruptive option, so treat it as a complement to the other methods rather than a replacement.
Attack surface review
This looks at your environment from the outside: exposed services, forgotten subdomains, open ports, credentials sitting in a leak. It's useful because it shows you what an attacker sees before they try to break in. For a deeper dive into attack surface management, view our guide here.