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7 Questions You Should Be Asking Your IT Provider Every Quarter (But Probably Aren’t)

June 09, 2025

If you only talk to your IT provider when it's time to renew your contract, you're missing the mark. Technology isn't something you can just set up once and forget about. It's always changing, and so are the threats that come with it. That's why quarterly IT check-ins are essential if you want your business to stay protected, efficient, and competitive.

But here's the catch: most business owners don't know what questions to ask. So today, here's a cheat sheet. These are the questions your IT provider should be able to answer every quarter—no jargon, no vague promises, just clear answers that help your business run smoothly.

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

This isn't about ticking boxes. You need to know:

- Is our antivirus current?

- Are there any unpatched systems?

- Have we experienced any near misses or warning signs lately?

You're not being paranoid, you're being prepared.

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

Backups are like seat belts—you don't think about them until you really need them. Ask:

- When was the last time a full restore was tested?

- Are we using the right backup strategy—off-site, cloud, hybrid?

- Are we backing up everything important?

- Is all backup data stored securely?

Many businesses assume they're backed up until they find out they're not.

3. Are All Employees Following Security Best Practices?

It only takes one person clicking the wrong link to compromise the entire network. Ask:

- Have there been any unusual logins or risky activities?

- Do we need another round of phishing training?

- Are employees using multifactor authentication?

Bonus points if your IT provider brings this up before you do—that means they're paying attention.

4. How Has Our Network Performance Been? Anything Slowing Us Down?

Slow systems mean slow teams and lost productivity (and money). Ask:

- Are there recurring performance issues?

- Are we outgrowing our hardware or software?

- Can anything be optimized to speed things up?

Even small improvements can make a big difference.

5. Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?

Regulations change, and so do the rules about storing and protecting data. Ask:

- Are we meeting current industry standards?

- Have any requirements changed recently?

- Do we need to update policies, software, or training?

Noncompliance fines can be costly. Stay ahead of them.

6. What Should We Be Budgeting For Next Quarter?

Good IT is proactive. Ask:

- Are any software licenses about to expire?

- Is any equipment nearing the end of its life?

- Are there upcoming projects we should prepare for?

This helps you avoid surprise expenses and plan effectively.

7. What Trends In IT Or Cybersecurity Are We Behind On That Are Making Us Slower Or More Vulnerable?

Technology and cyber threats don't stand still. Ask your IT provider:

- Are there new tools or best practices we're not using yet?

- Are we falling behind in any security protocols or performance standards?

- What are other businesses our size doing that we're not?

- Are there emerging threats we should be cautious about?

Falling behind on trends doesn't just slow you down—it leaves you exposed. A great IT partner keeps you ahead of the curve, not playing catch-up.

You Aren't Having These Conversations? Red Flag

If your IT provider can't clearly answer these questions—or worse, doesn't offer to meet with you quarterly—you may not be getting the support you need. Technology moves fast. Cyber threats move faster. You need someone who's not just fixing problems after they happen but actively working to prevent them.

We offer FREE Security Assessments to help business owners get a clear picture of their tech setup—what's working, what's not, and how to fix issues before they become problems.

Click here or call us at 408-335-0353 to book your Discovery Call