11 Questions You Should Be Asking About Your Company Cybersecurity

If your current security review consists of hoping nobody notices that dusty server in the back closet, it’s time to get serious. Below are eleven questions that will turn your cybersecurity from non-existent to a digital Fort Knox. 

1. What Is Our Risk Appetite and How Do We Quantify It?

Okay, so absolutely, the first question you should be asking yourself about cybersecurity is how much risk you are willing to take. Different companies have different risk thresholds, and this is perfectly fine as long as you know what yours is. 

Are you comfortable with a minor phishing incident that knocks email offline for an afternoon, or does your board demand zero tolerance for data exposure? Quantifying risk means working out how much each kind of threat will cost you and whether you are willing or able to shoulder that cost.

2. Have We Mapped Our Attack Surface Completely?

Your attack surface is the sum of all the points where an enemy could strike—web apps, servers, Wi-Fi networks, IoT devices, and even that old development laptop in the janitor’s closet. If you don’t know every system an unwelcome guest could exploit, you’re essentially leaving windows unlocked. An asset inventory exercise, supplemented by tools that scan for unauthorized devices and shadow IT, helps you discover every nook and cranny that needs protection.

3. How Do We Balance Automated Scanning with Continuous Penetration Testing?

Ah, the big continuous penetration testing vs. automated scanning debate, but does it have to be a debate at all? Automated scanning and continuous penetration testing are like peanut butter and jelly: great alone but even better together. Automated scanners can run daily checks for known vulnerabilities and misconfigurations, while continuous pen testing simulates real-world attacks around the clock. Using both ensures you catch low-hanging fruit swiftly, while still probing deep for business logic flaws or chained exploits that an automated tool might miss.

4. Are Our People Trained to Spot and Report Phishing Attempts?

Humans will always be part of the equation, so invest in turning your staff into a human firewall. Phishing simulations that resemble the latest AI-generated scams help employees learn to identify suspicious emails. Regular awareness training, micro-learning modules, and friendly competitions (who spots the phish fastest) reinforce good habits. When someone reports a dubious link, reward them with public kudos rather than a stern rebuke for making trouble.

5. Do We Have Multi-Factor Authentication Everywhere It Matters?

Passwords alone are like cardboard shields in a bullet-ridden world. Multi-factor authentication (MFA) adds a second or third barrier—texted codes, hardware tokens, or biometric scans. Critical systems like remote access portals, cloud consoles, and privileged accounts should all require MFA. Enforcing it company-wide dramatically reduces the chances that a leaked credential becomes a catastrophic breach.

6. What Is Our Patch Management Strategy?

Patching is the cybersecurity equivalent of dental hygiene: tedious but absolutely vital. Neglected updates create gaping holes for attackers to slip through. A robust patch management process categorizes updates by severity, schedules automatic deployments for low-risk patches, and assigns quick turnaround times—ideally 48 to 72 hours—for critical security fixes. Regular audits confirm that patches have applied correctly and haven’t broken anything important.

7. How Well Do We Monitor and Respond to Suspicious Activity?

Detection is only half the battle; you also have to respond swiftly. Implement a security information and event management (SIEM) system that aggregates logs from firewalls, endpoints, and cloud services. Machine learning-driven analytics can flag anomalies like unexpected login patterns or data transfers at odd hours. Pair this with an incident response playbook: who isolates systems, who communicates externally, and who leads the root cause analysis. Practice tabletop drills so everyone knows their role when the alarms go off.

8. Are We Encrypting Data at Rest and In Transit?

Unencrypted data is a neon sign reading “Free for the Taking.” Use strong encryption standards for all sensitive data—customer information, financial records, intellectual property—both at rest on disks and in transit across networks. SSL/TLS certificates, disk-level encryption, and encrypted backups ensure that even if an attacker grabs your files, they can’t read them. Regularly review your encryption protocols to keep ahead of evolving cryptographic recommendations.

9. What Is Our Third-Party and Supply Chain Risk Profile?

Your vendors are extensions of your network. A breach in a poorly secured supplier can cascade into your environment faster than you can say “zero day.” Conduct thorough security assessments of critical partners, require them to meet your minimum security standards, and maintain clear contractual obligations around incident notification. Continuous monitoring of vendor systems and periodic questionnaires help you catch supply chain risks before they land on your doorstep.

10. Do We Regularly Test and Improve Our Disaster Recovery Plan?

No security strategy is complete without a plan for when things go sideways. A disaster recovery plan (DRP) outlines how to restore critical operations after a major incident—ransomware, data center fire, or catastrophic network failure. Regularly schedule full-scale DR drills, including bringing backup systems online and validating data integrity. Measure recovery time objectives (RTOs) and recovery point objectives (RPOs) against business requirements. The goal is to ensure you can bounce back in hours, not weeks.

11. Are We Embracing Zero Trust Architecture?

Zero trust architecture flips the old “trust but verify” model on its head by treating every user and device as untrusted until they prove otherwise. Instead of assuming that someone within the network perimeter is safe, zero trust forces continuous authentication, least-privilege access, and micro-segmentation of resources. This way, if an attacker sneaks in through a compromised email or an unpatched VPN, they can’t roam freely. Implementing zero trust might mean adding identity-aware proxies, tightening conditional access policies, or isolating critical data in its own secure enclave. It’s a game-changer for reducing lateral movement, and ultimately, limiting the blast radius of any breach.

From Questions to Action

Asking the right questions is only the first step to success when it comes to cybersecurity, but of course, asking the questions alone is not enough, you have to act on them and act fast, or your business could remain unprotected. You need to turn these inquiries into a prioritized roadmap with clear ownership, measurable goals, and deadlines if you are to make your company as secure as possible. Oh, and the questions, along with the technology, will change in time to, so you need to make sure you stay abreast of all the latest developments. Do all of that, and your cybersecurity threat will get low and stay low.