The Business Technology Assessment Checklist: 40 Questions Every Owner Should Answer

Most business owners have a vague sense that their technology could be better—but they don't know where to start or what "better" looks like.

This self-assessment covers the key areas of business technology. Answer honestly, and you'll have a clear picture of where you stand and where to focus improvement efforts.

Section 1: Infrastructure Fundamentals (10 Questions)

The foundation everything else depends on.

✅ 1. Is your internet connection business-grade with an SLA?

Consumer connections (residential cable, DSL) don't come with uptime guarantees. Business-grade service includes service level agreements and priority repair.

✅ 2. Do you have automatic failover to a backup internet connection?

When your primary internet fails, does business stop? Cellular backup with automatic failover keeps you running.

✅ 3. Is your network equipment business-grade (not consumer)?

The $60 router from Best Buy wasn't designed for business-critical operations. Business equipment offers better performance, security, and manageability.

✅ 4. Is your WiFi adequate for your needs?

Dead zones, slow connections, and dropped calls indicate inadequate coverage or outdated equipment.

✅ 5. Are your workstations less than 5 years old?

Old computers slow productivity and often can't run current security software effectively.

✅ 6. Do you have adequate power protection (UPS) for critical systems?

Power surges and brief outages can damage equipment and corrupt data. UPS devices provide protection and graceful shutdown time.

✅ 7. Is your cabling organized and documented?

Spaghetti cabling causes problems and makes troubleshooting difficult. Proper cable management saves time and prevents issues.

✅ 8. Do you have a hardware refresh plan and budget?

Equipment doesn't last forever. Planning for replacement prevents surprise expenses and emergency purchases.

✅ 9. Is your server infrastructure adequate (on-premises or cloud)?

Whether you use local servers, cloud services, or a hybrid approach, is it meeting your performance and reliability needs?

✅ 10. Do you have documentation of your technology environment?

If your IT person left tomorrow, could someone else understand your setup? Documentation is essential for support and disaster recovery.

Section 2: Security Posture (10 Questions)

Protection against the threats that can end your business.

✅ 11. Does every employee have unique login credentials?

Shared accounts make security impossible. Every user needs their own account.

✅ 12. Is multi-factor authentication enabled on all critical systems?

MFA stops 99.9% of automated attacks. At minimum, enable on email, remote access, and banking.

✅ 13. Do you have modern endpoint protection (not just antivirus)?

Traditional antivirus misses modern threats. Endpoint Detection and Response (EDR) provides behavioral detection.

✅ 14. Is your network segmented appropriately?

Guest WiFi should be separate from business operations. IoT devices should be isolated. Critical systems should be protected.

✅ 15. Are software updates applied promptly?

60% of breaches involve unpatched vulnerabilities. Updates should be applied within days, not months.

✅ 16. Do you have email security beyond basic spam filtering?

Advanced threats bypass basic filters. You need attachment sandboxing, URL analysis, and impersonation protection.

✅ 17. Have employees received security awareness training in the past year?

Your employees are your first line of defense—and often your weakest link. Training matters.

✅ 18. Do you have a documented incident response plan?

When something goes wrong, panic makes it worse. A documented plan ensures systematic response.

✅ 19. Is sensitive data encrypted at rest and in transit?

Encryption protects data even if systems are compromised or devices are lost.

✅ 20. Do you know what data you have and where it lives?

You can't protect what you don't know about. Data classification and inventory are foundational.

Section 3: Backup and Business Continuity (10 Questions)

Your ability to survive disasters.

✅ 21. Is critical data backed up at least daily?

How much work can you afford to lose? Daily backups mean maximum one day of data loss.

✅ 22. Do you have at least one backup copy that ransomware cannot reach?

Air-gapped or immutable backups survive attacks that compromise your network.

✅ 23. Have you tested backup recovery in the past quarter?

Untested backups often fail when needed. Regular testing is essential.

✅ 24. Do you know your Recovery Time Objective (RTO)?

How quickly do you need to be operational after a disaster? Your backup strategy should support this goal.

✅ 25. Do you know your Recovery Point Objective (RPO)?

How much data can you afford to lose? This determines backup frequency.

✅ 26. Do you have a documented disaster recovery plan?

Beyond backups, do you know how to actually recover? Who does what? In what order?

✅ 27. Can critical employees work remotely if the office is inaccessible?

Fire, flood, construction—many events can close an office. Can work continue?

✅ 28. Do you have cyber insurance?

Cyber incidents are expensive. Insurance provides financial protection for incidents that get through your defenses.

✅ 29. Do key vendors have documented contact information for emergencies?

In a crisis, you need to reach people quickly. Is that information documented and accessible?

✅ 30. Have you practiced your disaster recovery procedures?

Tabletop exercises or actual drills reveal gaps before real disasters expose them.

Section 4: Productivity and Efficiency (10 Questions)

Getting the most from your technology investment.

✅ 31. Do employees have the tools they need to do their jobs efficiently?

Are people working around technology limitations? Are manual processes slowing work?

✅ 32. Are your core business applications meeting your needs?

Are you outgrowing software? Are there better options available?

✅ 33. Is information easy to find and share appropriately?

Do people waste time searching for documents? Is collaboration smooth or frustrating?

✅ 34. Do your systems integrate with each other?

Or do employees manually transfer data between systems, risking errors and wasting time?

✅ 35. Is remote work well-supported?

Can employees work effectively from anywhere, or are there significant limitations?

✅ 36. Do you have adequate communication tools?

Phone systems, video conferencing, chat—do they work well and integrate properly?

✅ 37. Are routine IT tasks automated where possible?

User provisioning, software updates, backups—automation reduces errors and frees time.

✅ 38. Do employees know how to use their technology effectively?

Training gaps mean underutilized tools and frustrated users.

✅ 39. Is IT support responsive when issues arise?

How long do employees wait for help? Does support actually solve problems?

✅ 40. Does technology support your business goals?

Beyond keeping things running, does IT enable growth, efficiency, and competitive advantage?

Scoring Your Assessment

Count Your "Yes" Answers

35-40: Strong technology foundation. Focus on optimization and strategic advantage.

25-34: Good foundation with gaps. Prioritize security and backup weaknesses first.

15-24: Significant risk exposure. Critical areas need immediate attention.

Under 15: High risk. Consider a comprehensive assessment and remediation plan.

Priority Areas by Risk

Address immediately:

• No MFA on email and remote access (Questions 12)
• No ransomware-proof backups (Question 22)
• No backup testing (Question 23)
• Shared user accounts (Question 11)

Address within 30 days:

• Basic antivirus only (Question 13)
• No network segmentation (Question 14)
• Delayed patching (Question 15)
• No incident response plan (Question 18)

Address within 90 days:

• Remaining security gaps
• Infrastructure improvements
• Productivity enhancements
• Documentation gaps

What Comes Next

This self-assessment gives you a starting point. For a comprehensive understanding of your technology environment, consider a professional assessment that includes:

• Technical vulnerability scanning
• Network architecture review
• Security posture evaluation
• Compliance gap analysis
• Strategic alignment review

Layth Solutions has been assessing and improving business technology in the NYC area for 30 years. We provide honest evaluations and practical recommendations—not scare tactics or unnecessary complexity.

Schedule a free technology assessment to understand exactly where you stand and what it would take to check every box on this list.