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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 contacting 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 about in your business. It's always changing, and so are the risks involved. 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 helpful guide. These are the questions your IT provider should be ready to answer every quarter—no jargon, no vague answers, just clear information that helps keep your business running smoothly.

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

This goes beyond ticking boxes. You need to find out:

- Is our antivirus software current?

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

- Have there been any recent close calls or warning signs?

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

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 the right files and systems being backed up?

- Is everything backed up and stored securely?

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

3. Are All Employees Following Security Best Practices?

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

- Have there been any unusual logins or risky behaviors?

- Do we need another round of phishing or security training?

- Are employees using multifactor authentication?

If your IT provider brings this up before you ask, that's a good sign they're vigilant.

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

Slow systems mean slow teams, which means lost productivity and money. Ask:

- Are there recurring performance problems?

- Are we outgrowing our current hardware or software?

- What can be optimized to improve speed?

Even small improvements can have a big impact.

5. Are We Still Compliant?

Regulations and data protection rules change frequently. Ask:

- Are we meeting the current standards for our industry?

- Have any compliance requirements changed recently?

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

Noncompliance fines can be costly. Staying ahead is crucial.

6. What Should We Be Budgeting For Next Quarter?

Good IT management is proactive. Ask:

- Are any software licenses about to expire?

- Is any equipment nearing the end of its useful life?

- Are there upcoming projects we should prepare for?

This helps you avoid unexpected 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 evolve constantly. Ask:

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

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

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

- Are there emerging threats we need to watch out for?

Falling behind on trends doesn't just slow you down; it puts you at risk. A strong 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 suggest quarterly meetings—you may not be getting the support your business needs.

Technology changes fast. Cyber threats move even faster.

You need someone who doesn't just fix problems after they happen but works proactively to stop them before they start.

We offer a FREE 15-Minute Discovery Call 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 615-989-0000 to book your 15-Minute Discovery Call today!