When was your last quarterly IT review?

If your answer is “When we signed our contract,” that’s a red flag. Today’s technology landscape evolves rapidly—and so do the threats. Cyberattacks, compliance standards, and operational inefficiencies don’t wait until your next budget meeting to strike. That’s why regular IT strategy check-ins—at least once a quarter—are critical to keeping your business secure, productive, and future-ready.

But here’s the challenge: most business owners don’t know what to ask during those quarterly meetings. You’re not expected to speak “tech.” You just need the right questions to guide the conversation.

Whether you’re running a CPA firm, dental office, law practice, or manufacturing company, here are the 7 must-ask questions your IT provider should be ready to answer—clearly, confidently, and without the jargon.

1. Are There Any Security Vulnerabilities We Need to Fix Right Now?

Cyberthreats don’t wait for permission. Ask your provider:

• Are all antivirus and threat detection systems up to date?

• Have any red flags or “near misses” been detected?

• Are all devices and software fully patched?

You’re not being paranoid—you’re being responsible. A good IT partner won’t just give you technical stats; they’ll give you peace of mind.

2. What’s the Current Status of Our Backups? And Have They Been Tested?

Backups are your last line of defense—but they’re worthless if they don’t work.

• Are we using the right backup strategy (on-prem, cloud, or hybrid)?

• When was the last full restore test completed?

• Are we backing up everything that matters—securely?

Many businesses assume their backups are fine—until it’s too late. A quarterly IT review should include a backup status check.

3. Are Employees Following Cybersecurity Best Practices?

One bad click can compromise your entire business.

• Are all users using multifactor authentication (MFA)?

• Have any users triggered alerts or suspicious activity?

• Are we due for another round of phishing or cybersecurity awareness training?

This is especially important in industries with sensitive data like healthcare, legal, and finance. An IT provider that tracks user behavior and training trends shows they’re protecting your people as well as your systems.

4. How’s Our Network Performance? Are We Slowing Down?

Tech that drags down your team is costing you money.

• Are there any recurring slowdowns or bottlenecks?

• Is outdated hardware or software holding us back?

• Can we optimize anything for speed and efficiency?

Your quarterly check-in should uncover small changes that make a big difference in performance.

5. Are We Still Fully Compliant With Our Industry Regulations?

Whether you’re governed by HIPAA, PCI-DSS, SOX, or other frameworks, compliance is non-negotiable.

• Have any new requirements or risks emerged recently?

• Are our policies, security tools, and user training still up to standard?

• Do we need to update or document anything for audit readiness?

Noncompliance can mean steep fines and reputational damage. A quarterly IT review helps keep you ahead of the curve.

6. What Should We Be Budgeting for in the Next Quarter?

Proactive IT is also predictable IT.

• Any software licenses about to expire?

• Any aging devices nearing end-of-life?

• Any planned projects we should prepare for?

When you plan ahead, you avoid nasty surprises—and you make smarter investments.

7. What Technology Trends or Cyber Threats Should We Be Aware Of?

Cybercriminals are innovating. So should your IT strategy.

• Are we missing out on modern tools or best practices?

• Are we lagging in any performance or security benchmarks?

• Are other businesses our size doing something we’re not?

A forward-thinking IT partner won’t just maintain the status quo—they’ll position you for what’s next.

Not Having These Conversations? It’s Time for a Change

If your current provider isn’t initiating quarterly IT reviews or can’t answer these questions confidently, you may be settling for reactive support instead of proactive partnership.

At Iler Networking & Computing, we help professional service firms like yours stay ahead of threats, avoid costly downtime, and stay compliant with changing regulations. Our quarterly reviews are built into every service tier because your business deserves more than break-fix support—it deserves a strategic partner.

Request your FREE Security & Systems Assessment today to find out exactly where you stand—and how to get ahead.