Two men discussing IT questions with icons of security, money, server, and alerts around them in a business setting

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 point.

Technology isn't something you set up once and forget. It's always changing, and so are the risks involved. That's why quarterly IT check-ins are essential if you want your business to stay safe, efficient, and competitive.

But here's the problem: 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 ready to answer every quarter—no jargon, no vague promises, just clear answers that keep your business running smoothly.

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

This goes beyond ticking boxes. You need to know:

- Is our antivirus 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 prepared.

2. What's The Status Of Our Backups? 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 full restore test?

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

- Are we backing up the right data?

- Is everything backed up and stored securely?

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

3. Are All Employees Following Security Best Practices?

One wrong click can bring down your entire network. Ask:

- Have there been any unusual logins or risky actions?

- 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 means they're paying attention.

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

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

- Are there recurring performance problems?

- Are we outgrowing our current hardware or software?

- Is there anything we can optimize to speed things up?

Even small improvements can make a big difference.

5. Are We Still Compliant?

Rules change, and so do data protection requirements. 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 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 need to plan for?

This helps you avoid surprise expenses and plan effectively.

7. What IT Or Cybersecurity Trends Are We Behind On That Could Be Slowing Us Down Or Increasing Risk?

Technology and cyber threats keep evolving. Ask your IT provider:

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

- Are we behind on any security protocols or performance benchmarks?

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

- Are there new threats we should watch out for?

Falling behind on trends doesn't just slow you down—it leaves you vulnerable. A good IT partner keeps you ahead, not playing catch-up.

You Aren't Having These Conversations? That's A 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 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 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 817-589-0808 to book your 15-Minute Discovery Call today!