7 Questions You Should Be Asking Your IT Provider Every Quarter

If the only time you hear from your IT provider is when it’s time to re-sign the contract or cut another check—you’re flying blind.

Tech isn’t like the breakroom fridge. You can’t just plug it in and forget it.

It’s always moving. New updates. New threats. New ways your team can get tripped up (or taken down) without warning.

That’s why we believe every small business—from dental clinics in Beaumont to contractors in Lake Charles—needs regular, plain-English check-ins with their IT partner. No buzzwords. No mystery fees. Just honest updates to keep your business protected and productive.

Not sure what to ask? Don’t worry—we’ve got your cheat sheet.

1. Are We Sitting On Any Tech Time Bombs?
Translation: Are we patched up? Protected? Or just crossing our fingers?

Ask:

  • Is our antivirus up to date?
  • Any near misses or weird activity lately?
  • Any unpatched holes we’re ignoring?

This isn’t paranoia. It’s preparedness. The difference between a quiet Tuesday and a panicked Wednesday.

2. Are Our Backups Actually Working—or Just There for Show?
If your last backup was during Mardi Gras… that’s a problem.

Ask:

  • When’s the last time you tested a full restore?
  • Are we backing up the right stuff? And is it secure?
  • Are we using the right method—cloud, off-site, hybrid?

Too many folks think they’re covered—until they’re not.

3. Is My Team Playing It Safe—Or Accidentally Inviting Trouble?
One click. That’s all it takes.

Ask:

  • Any red flags in user behavior?
  • Do we need a fresh round of phishing training?
  • Is multifactor authentication turned on for everyone?

A good IT partner brings this up before you have to ask.

4. Is Anything Slowing Us Down—And Can We Fix It?
Slow tech drags everything with it: morale, money, momentum.

Ask:

  • Any hardware about to croak?
  • Are we outgrowing our setup?
  • Can we tweak something to boost speed?

Sometimes a small fix gives you a big win.

5. Are We Still Playing by the Rules? (HIPAA, PCI-DSS, You Name It)
Compliance isn’t just about paperwork. It’s about peace of mind.

Ask:

  • Are we still in the clear with our industry’s rules?
  • Any new requirements we need to know about?
  • Do we need to update policies or training?

Skipping this step could cost you thousands.

6. What’s Coming Down the Pipe Next Quarter?
No one likes surprise expenses—especially not small business owners.

Ask:

  • Any software renewals or license changes?
  • Equipment we’ll need to replace soon?
  • Projects we should be budgeting for now?

A little planning today saves a lot of scrambling tomorrow.

7. Are We Behind On Anything That’s Making Us Slower or More Exposed?
The tech world moves fast. Cybercriminals move faster.

Ask:

  • Any best practices we’re missing out on?
  • Are we lagging on performance or security?
  • What are other businesses our size doing that we’re not?
  • Are there new threats we need to stay ahead of?

Falling behind isn’t just inefficient—it’s dangerous.

If You’re Not Having These Conversations, That’s a Red Flag

If your IT provider doesn’t have clear answers—or isn’t even asking for these meetings—that’s a problem.

You deserve better.

We offer FREE Security Assessments to help local businesses like yours get a clear picture of where you stand—and what to fix before it breaks.

Click here to book your FREE assessment today
Let’s make sure your tech’s doing its job, so you can focus on yours.