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

June 09, 2025

If you're only communicating with 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 and forget. It's always changing, and so are the risks that come with it. That's why having quarterly IT check-ins is essential if you want your business to remain secure, efficient, and competitive.

The problem is, most business owners don't know what questions to ask.

So here's a cheat sheet. These are the questions your IT provider should be prepared to answer every quarter—no jargon, no vague responses, just clear answers that keep your business running smoothly.

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

This isn't just a checklist item. You need to know:

- Is our antivirus software current?

- Are there any systems that haven't been patched?

- Have there been any recent near misses or warning signs?

You're not being paranoid; you're being proactive.

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

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

- When was the last full restore test?

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

- Are we backing up the right data?

- Is everything backed up and stored securely?

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

3. Are All Employees Following Security Best Practices?

One wrong click can 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?

If your IT provider raises these issues before you do, that's a good sign they're vigilant.

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

Slow systems mean slow teams and lost productivity. Ask:

- Are there recurring performance problems?

- Are we outgrowing our current hardware or software?

- Can anything be optimized to improve speed?

Even small improvements can have a big impact.

5. Are We Still Compliant?

Regulations evolve, and so do data protection requirements. Ask:

- Are we meeting all industry standards?

- Have any compliance requirements changed?

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

Noncompliance fines can be costly. Staying ahead is critical.

6. What Should We Be Budgeting For Next Quarter?

Effective IT is about planning ahead. Ask:

- Are any software licenses about to expire?

- Is any equipment nearing the end of its lifecycle?

- Are there upcoming projects we should prepare for?

This helps you avoid unexpected costs 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 constantly evolve. Ask your IT provider:

- Are there new tools or best practices we haven't adopted yet?

- Are we falling behind on security protocols or performance standards?

- What are comparable businesses doing that we aren't?

- Are there emerging threats we should be aware of?

Falling behind doesn't just slow you down—it puts you at risk. A great IT partner keeps you ahead, not playing catch-up.

You Aren't Having These Conversations? Red Flag

If your IT provider can't give clear answers to these questions—or worse, doesn't offer regular quarterly meetings—you might not be getting the support you need.

Technology changes quickly. Cyber threats move even faster.

You need someone who's not just fixing problems after they happen but actively working to prevent them in the first place.

We offer a FREE 10-Minute Conversation to help business owners like you get a clear view of their tech setup - what's working, what's not and how to fix it before it turns into a problem.

Click here or give us a call at 435-313-8132 to book your 10-Minute Conversation today!