7 Must-Ask Questions For Your IT Provider During Each Quarterly Review (Most Businesses Overlook These)

If the only time you’re connecting with your IT provider is during contract renewals, you’re missing a big opportunity.

Technology isn’t something you set up once and then forget about. It’s always changing—and so are the risks tied to it. That’s why meeting with your IT team every quarter isn’t optional if you want to keep your operations secure, efficient, and ahead of the curve.

The challenge? Most business leaders aren’t sure what they should be asking.

That’s why we’ve put together a quick reference guide. These are the key questions your IT provider should confidently answer every quarter—without the jargon or empty assurances—so your business stays on track and protected.

1. Do We Have Any Immediate Security Gaps That Need Attention?
   
   This goes beyond routine checklists. You should be asking:
   
   
   • Is our antivirus software current and functioning properly?
   • Are there any systems that haven’t been patched or updated?
   • Have there been any recent warning signs or close calls?
   
   You’re not being paranoid – you’re being prepared.
2. How Reliable Are Our Backups? And Have They Been Tested Recently?
   
   Backups are like insurance: you don’t appreciate their value until something goes wrong. Make sure to ask:
   
   
   • When did you last perform a full restore test?
   • Is our current backup method appropriate? Are we using cloud, off-site, or a hybrid solution?
   • Are we backing up the most critical data and systems?
   • Is all backup data stored safely and securely?
   
   Many businesses assume their backups are solid—until they find out the hard way they aren’t.
3. Are All Team Members Adhering To Security Protocols?
   
   A single employee making a mistake can jeopardize the entire network. Make sure to ask:
   
   
   • Have there been any suspicious logins or actions?
   • Is it time for another round of phishing awareness training?
   • Are employees utilizing multi-factor authentication?
   
   It’s a good sign if your IT provider brings this up proactively. That’s how you know they’re staying vigilant.
4. How Is Our Network Performing? Are There Any Bottlenecks?
   
   Slow systems = sluggish teams = lost productivity (and potential revenue). Be sure to ask:
   
   
   • Are there any ongoing performance problems?
   • Is our current hardware or software holding us back as we grow?
   • Are there areas we can optimize to improve speed?
   
   Sometimes, even small adjustments can have a significant impact.
5. Are We Still In Compliance With [HIPAA, PCI-DSS, GDPR, etc.]?
   
   Regulations evolve, and so do the requirements for safeguarding your data. Be sure to ask:
   
   
   • Are we still meeting the necessary standards for our industry?
   • Have there been any updates to compliance requirements?
   • Do we need to revise policies, software, or training to stay current?
   
   The costs of noncompliance can be steep—staying proactive can save you a lot.
6. What Should We Be Allocating In The Budget For The Upcoming Quarter?
   
   Proactive IT planning is key. Ask:
   
   
   • Are any software licenses set to expire soon?
   • Is any equipment approaching its end-of-life?
   • Are there any projects we should be preparing for?
   
   This approach helps you avoid unexpected costs and plan with confidence.
7. What IT Or Cybersecurity Trends Are We Missing That Could Be Slowing Us Down Or Increasing Our Risks?
   
   Technology is always evolving—and so are cyber threats. Ask your IT provider:
   
   
   • Are there any new tools or best practices we should be adopting?
   • Are we falling behind on any security protocols or performance standards?
   • What are other companies of our size doing that we aren’t?
   • Are there any emerging threats we should be preparing for?
   
   Ignoring the latest trends doesn’t just slow progress—it leaves you vulnerable. A strong IT partner will keep you ahead of the game, not scrambling to catch up.



NOT Having These Conversations? That’s a Red Flag.




If your IT provider can’t provide clear answers to these questions—or, even worse, isn’t proactively offering quarterly check-ins—you may not be receiving the support you truly need.




Technology evolves rapidly, and cyber threats evolve even quicker.




You deserve a partner who doesn’t just respond to problems—but works proactively to stop them from happening at all.




We provide FREE IT Systems Assessments to help business owners gain a clear understanding of their current technology—what’s functioning well, what needs improvement, and how to fix potential issues before they disrupt your operations.




Click here to schedule your assessment today!