23 yes/no questions that show you exactly where your IT security stands. Built for healthcare practices, law firms, and financial services companies. Answer honestly — nobody sees your results but you.
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Security Fundamentals
1. Do all employees use multi-factor authentication (MFA) for email and critical systems?
2. Is antivirus/EDR software installed AND actively monitored on every device?
3. Are all operating systems and applications patched within 30 days of updates being released?
4. Do you have automatic, tested backups of all critical business data?
5. Have you tested restoring from a backup in the past 6 months?
6. Are employees required to use strong, unique passwords (or a password manager)?
7. Is your Wi-Fi network secured with WPA2/WPA3 and a guest network separated from business systems?
8. Do former employees lose ALL system access within 24 hours of departure?
Compliance & Data Protection
9. Do you have a documented risk assessment from the past 12 months?
10. Do you have signed Business Associate Agreements (BAAs) with EVERY vendor that touches sensitive data?
11. Does your website contact form route through a HIPAA-compliant (or equivalent) processor?
12. Is sensitive data encrypted both in transit (TLS) and at rest (AES-256)?
13. Do you maintain written records of employee security training?
14. Do you know exactly where all your sensitive client/patient data is stored?
15. Do you have a written incident response plan for a breach or ransomware event?
16. Could you produce compliance documentation within 48 hours if audited?
IT Vendor & Oversight
17. Does your IT provider send you a monthly written report with real metrics?
18. Can you name the specific people responsible for your IT security?
19. Do you know your current patch compliance rate?
20. Has your IT provider ever shown you a security posture score for your business?
21. Do you know what your IT provider would do in the first hour of a ransomware attack?
22. Is your IT spending predictable — no surprise invoices in the past 6 months?
23. If you asked your IT provider for proof that monitoring is active right now, could they show you today?
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Your gaps — in priority order
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