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 isn't something you can just set up and forget. It's always changing, and so are the security risks that come with it. That's why quarterly IT check-ins are 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 of questions your IT provider should be able to answer every quarter—no jargon, no vague answers, just straightforward information to 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 software current?
- Are there any systems that haven't been patched?
- Have there been any recent warnings or close calls?
You're not being overly cautious—you're being prepared.
2. What's The Status Of Our Backups? Have They Been Tested 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 best backup strategy (off-site, cloud, hybrid)?
- Are we backing up the right data?
- 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?
One wrong click by an employee can compromise the entire network. Ask:
- Have there been any unusual login attempts or risky actions?
- Is it time for another phishing awareness training?
- Are employees using multifactor authentication?
Bonus points if your IT provider brings these issues up before you ask—that shows they're vigilant.
4. How Has Our Network Performance Been? Is Anything Causing Slowdowns?
Slow systems mean slow teams and lost productivity. Ask:
- Are there recurring performance problems?
- Are we outgrowing our current hardware or software?
- Can we optimize anything to improve speed?
Even minor improvements can have a big impact.
5. Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?
Regulations and data protection rules change regularly. 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—stay ahead of them.
6. What Should We Be Budgeting For Next Quarter?
Good IT management is proactive. Ask:
- Are any software licenses expiring soon?
- Is any equipment nearing the end of its useful life?
- Are there upcoming projects we should prepare for?
This helps you avoid surprise costs and plan effectively.
7. What IT or Cybersecurity Trends Are We Behind On That Could Be Slowing Us Down or Increasing Our Risk?
Technology and cyber threats evolve constantly. Ask:
- Are there new tools or best practices we should adopt?
- Are we behind on any security protocols or performance standards?
- What are other businesses our size doing that we're not?
- Are there emerging threats we need to watch out for?
Falling behind on trends not only slows you down but also leaves you vulnerable. A great 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 suggest quarterly meetings—you may not be getting the support your business needs. Technology changes fast, and cyber threats move even faster. You need a partner who's not just fixing problems after they happen but actively working to prevent them.
We offer a free Discovery Call to help business owners like you get a clear picture of your technology setup—what's working, what isn't, and how to fix issues before they become problems.
Click here or call us at (210) 582-5814 to book your Discovery Call
