June 09, 2025
7 Questions You Should Be Asking Your IT Provider Twice a Year (At Minimum)
(…And Quarterly in Larger or Highly Data Sensitive Environments)
If the only time you talk to your IT provider is when your contract's up for renewal...
You're not getting the value you should be.
Technology isn't "set it and forget it."
It's evolving constantly—and so are the cyberthreats, compliance requirements, and productivity tools that go with it.
That's why at a minimum, you should be sitting down with your IT partner twice a year.
And if your business is larger than 50 users, handles regulated data, remote teams, or rapid growth, a quarterly check-in is essential.
❓ What Should You Ask During These Strategy Sessions?
We've put together a cheat sheet of 7 must-ask questions your IT provider should be ready to answer—clearly, proactively, and without a bunch of confusing tech jargon.
Whether you meet twice a year or quarterly, these questions ensure your business stays secure, efficient, and prepared.
1. 🛡️ Are There Any Vulnerabilities We Need to Address Right Now?
This isn't paranoia—it's preparation. Ask:
-
Are our antivirus and endpoint protection tools fully up-to-date?
-
Do we have any unpatched systems or software?
-
Have there been any recent red flags or suspicious activity?
Your IT partner should be looking for trouble before it finds you.
2. 💾 What's the Status of Our Backups? Have You Tested Them Recently?
Backups are like seat belts: you won't care—until you crash.
Ask your provider:
-
When was the last time you tested a full restore?
-
Are we using the right strategy (off-site, cloud, or hybrid)?
-
Are we backing up all the right data—and is it stored securely?
Too many businesses think they're backed up… until they try to recover.
3. 🧑💻 Are All Employees Following Security Best Practices?
All it takes is one bad click to take down your network.
Ask:
-
Have there been any unusual login attempts or behaviors?
-
Are employees using MFA (multifactor authentication)?
-
Should we run another round of phishing training?
Your IT partner should be tracking this proactively—if they're not, it's a red flag.
4. 🚀 How Has Our Network Performance Been? Anything Slowing Us Down?
Slow systems lead to frustrated employees and lost revenue.
Ask:
-
Are we experiencing recurring speed or connectivity issues?
-
Are any tools, devices, or systems outdated?
-
Is there anything we can optimize?
Sometimes small tweaks = big productivity gains.
5. 📋 Are We Still Compliant With Industry Regulations (HIPAA, PCI-DSS, etc.)?
Regulations change fast—and staying compliant is critical.
Ask:
-
Are we meeting our industry's cybersecurity standards?
-
Have any rules changed recently?
-
Do we need to update documentation, tools, or training?
Compliance fines aren't cheap. Neither are lawsuits.
6. 💸 What Should We Be Budgeting for Next Quarter?
Smart IT is predictable, not reactive.
Ask:
-
Are any software licenses or support contracts expiring?
-
Are we due for any hardware refreshes?
-
Should we be planning for any IT projects or upgrades?
This keeps you in control of your IT spend and avoids last-minute surprises.
7. ⚠️ What IT or Cybersecurity Trends Are We Falling Behind On?
Tech moves fast—and if you're not evolving, you're exposed.
Ask:
-
Are there any new tools or protocols we should be considering?
-
How do we compare to other businesses our size?
-
Are there any rising threats we need to prepare for?
A strong IT provider helps you stay ahead of the curve—not play catch-up.
🚨 Not Having These Conversations At Least Twice a Year? That's a Problem.
If your IT provider can't clearly answer these questions—or worse, isn't scheduling regular check-ins at all—you might not be getting the strategic support your business needs.
Technology changes quickly.
Cyberthreats move even faster.
You deserve a partner who's not just fixing problems, but helping you stay ahead of them.
🎯 Ready for a Strategic IT Review?
Let's walk through your current setup, flag risks, and help you plan smarter for the next 6 to 12 months.