7 Questions You Should Be Asking Your IT Provider Every Quarter (But Probably Aren’t)

Let's be honest: if the only time you hear from your IT provider is when it's time to renew your contract, something's off.

Tech isn't "set it and forget it." It shifts faster than Florida weather—and the risks that come with it move just as quick. That's why every business should be sitting down with their IT team at least once a quarter.

But here's the rub: most business owners don't know what to ask. And most providers? They're happy to keep it that way.

Not on our watch. Here's your cheat sheet—seven questions you should be asking your IT provider every 90 days. No jargon, no guesswork. Just straight answers that keep your business running smooth and secure.

1. Are There Any Red Flags or Security Holes We Need to Fix Right Now?

This isn't being paranoid—it's being smart.

• Is our antivirus current?
• Are any systems unpatched or out of date?
• Have there been any "near misses" or suspicious activity?

Your IT folks should be keeping an eye on this without you asking. But if they're not bringing it up? Ask.

2. Are Our Backups Actually Working—and When's the Last Time You Tested One?

Backups are like spare tires. Useless if they're flat.

• When was the last full restore test?
• Are we backing up everything we should be?
• Is our backup off-site, in the cloud, or both?
• Is it secure?

Plenty of businesses think they're covered… right up until they aren't.

3. Is My Team Following Security Best Practices—or Are We at Risk From Inside?

It only takes one click on a bad link to bring down the house.

• Are risky logins or behaviors showing up?
• Are folks skipping multi-factor authentication?
• Do we need a refresher on phishing training?

A good provider spots patterns before they become problems.

4. Is Anything Slowing Down Our Network or Systems?

Because slow tech equals slow work.

• Are we bottlenecked anywhere?
• Is our hardware aging out?
• Can anything be tuned up for better speed?

Sometimes it's a small fix. Sometimes it's a bigger overhaul. Either way, you should know.

5. Are We Still in Compliance With the Rules That Matter to Our Industry?

Regulations don't sit still. Neither should your policies.

• Are we up to date with HIPAA, PCI-DSS, FTC Safeguards, or whatever applies?
• Have any requirements changed?
• Do we need new training, updates, or documentation?

You don't want to find out you're non-compliant during an audit.

6. What Should We Be Budgeting For in the Next Quarter?

Proactive IT means no surprises.

• Any upcoming renewals or license changes?
• Equipment nearing retirement?
• Any new projects or upgrades we should prepare for?

Planning ahead avoids panic—and keeps costs predictable.

7. What New Tech or Threats Should Be on Our Radar?

The tech world changes fast. Cyber crooks move faster.

• Are there tools we're missing out on?
• Are we behind on important protocols?
• What are other businesses our size doing differently?
• Any new threats we need to brace for?

Your IT provider should be helping you lead—not lag.

If These Conversations Aren't Happening, That's a Red Flag

Quarterly check-ins should be the minimum standard. If your provider isn't showing up with answers—or isn't showing up at all—it might be time to rethink the relationship.

We offer FREE Security Assessments to help you get the full picture of your current setup. No pressure, no nonsense—just clear answers on what's working, what's not, and what needs fixing before it turns into a full-blown problem.

👉 [Click here to book your FREE assessment now.]

Because peace of mind doesn't come from crossing your fingers—it comes from asking the right questions.