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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 is not something you can just set up and forget. It's always changing, and so are the risks associated 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 today, here's a simple guide. These are the questions your IT provider should be prepared to answer every quarter—no technical jargon, no vague answers, just clear information to keep your business running smoothly.

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

This is more than just ticking boxes. You need to know:

- Is our antivirus software current?

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

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

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 time a full restore was tested?

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

- Are we backing up the right data?

- Is all backup data stored securely?

Many businesses believe they're backed up until they discover they're not.

3. Are All Employees Following Security Best Practices?

It only takes one person clicking the wrong link to compromise your 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 ask—that shows they're paying attention.

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

Slow systems equal slow teams, which means lost productivity and money. 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 the rules about data storage and protection. Ask:

- Are we meeting industry standards?

- Have any compliance requirements changed?

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

Noncompliance fines can be costly. Stay ahead to avoid them.

6. What Should We Be Budgeting For Next Quarter?

Good IT is about being proactive. Ask:

- Are any software licenses about to expire?

- Is any equipment nearing the end of its lifespan?

- 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 keep evolving. Ask:

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

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

- What are similar businesses doing that we're not?

- Are there emerging threats we should be aware of?

Falling behind on trends doesn't just slow you down; it leaves you exposed. A great IT partner keeps you ahead, not catching 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 even suggest meeting quarterly—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 preventing them.

We help business owners like you get a clear understanding of their technology—what's working, what's not, and how to fix issues before they become problems.

Click here or give us a call at 332-217-0601 to Speak to an Expert today!