If you’re only talking to your IT provider during contract renewal season, it’s time to change that.

Your technology isn’t a “set it and forget it” feature—it’s a critical piece of your day-to-day operations and your cybersecurity defense. Cyber threats are evolving constantly, and without routine check-ins, your business could be left vulnerable. The solution? Quarterly IT reviews that go beyond surface-level updates.

But most business owners don’t know the right questions to ask. That’s why we’ve created a cheat sheet of essential topics that your provider should be ready to answer—every quarter.

1. Are There Any Vulnerabilities We Need To Address Right Now?

Your IT partner should be proactively identifying risks, not just reacting when something breaks. During your quarterly check-in, ask:

  • Are antivirus programs and firewalls up to date?

  • Are there any unpatched systems?

  • Have we had any near misses or attempted intrusions?

You’re not being paranoid—you’re preparing for reality. And your provider should back that up with data.

2. What’s The Status Of Our Backups? Have You Tested Them Recently?

Assuming your backups are working is dangerous. Ask about:

  • The last time a full restore was tested

  • The type of backup strategy in place (cloud, on-prem, hybrid)

  • Whether critical files, databases, and user directories are included

If your business is hit by ransomware or a hardware failure, a good backup strategy is your only way out.

3. Are Employees Following Security Best Practices?

Security is only as strong as your weakest user. Ask your provider:

  • Have there been any suspicious login attempts or user behavior?

  • Is everyone using multifactor authentication?

  • Should we schedule another round of phishing training?

Signing up for our weekly Cybersecurity Tech Tips is another smart way to keep your staff up to date.

4. How’s Our Network Performance? Are There Any Bottlenecks?

IT isn’t just about security—it’s about keeping your team productive. During your meeting, check in on:

  • Recurring slowdowns or outages

  • Aging hardware or licenses near expiration

  • Opportunities to optimize workflows or infrastructure

Slow systems waste time and money. A Managed IT Services provider should help you prevent those issues before they impact your bottom line.

5. Are We Still Compliant With Industry Regulations?

HIPAA, PCI-DSS, GDPR—whatever applies to your business, compliance is non-negotiable. Ask:

  • Are our systems up to code?

  • Have any requirements changed recently?

  • Do we need to update our documentation, training, or software?

Fines for noncompliance are steep. Your provider should keep you informed and compliant.

6. What Should We Budget For Next Quarter?

Avoid surprise expenses by getting ahead of them:

  • Are there renewals coming up?

  • Any upgrades or replacements due?

  • Should we plan for any infrastructure changes?

Book a discovery call and we’ll help you map out a smarter, more secure IT plan.

7. What Are We Behind On—And What Should We Be Looking Ahead To?

Tech evolves fast. Your provider should help you stay competitive and protected by addressing:

  • New tools or platforms your industry is adopting

  • Security protocols you’re not using yet

  • Emerging cyber threats that could impact your business

Don’t wait for a breach to start updating your tech stack.

Not Having These Conversations? That’s a Red Flag

If your provider can’t answer these questions—or worse, isn’t offering regular meetings at all—it might be time to rethink your IT strategy. You deserve a proactive partner, not a passive one.

Start with a free Security Assessment. We’ll identify vulnerabilities, optimize your setup, and make sure your tech is helping—not holding you back.

Click here to schedule your FREE Network Assessment.