7 Questions You Should Ask Your IT Provider Every Quarter (But Probably Don’t)

If you only talk to your IT provider once a year, you’re doing it wrong.

Tech changes fast. Threats change faster. You can’t just “set it and forget it.” To keep your business safe and moving, you need regular IT check-ins. Every three months, at least. But what should you ask?

Most business owners don’t know. That’s fine. Here’s your list. No jargon. No fluff. Just the questions that matter, and the answers you should expect.

1. "Are we exposed to any security risks right now?"

This is more than a basic check. Ask:

• Is antivirus up to date?

• Are there any unpatched systems?

• Any recent alerts or close calls?

If your provider doesn’t know, you’re flying blind.

2. "Are our backups working, and have you tested them?"

Backups fail. Often. Ask:

• When was the last full restore test?

• Is the backup off-site, in the cloud, or both?

• Are we backing up the right files?

• Is the storage secure?

Don’t wait for disaster to find out the answer.

3. "Are our people following security basics?"

One bad click can take down your whole network. Ask:

• Any odd logins or suspicious activity?

• Should we retrain on phishing?

• Is multifactor authentication (MFA) being used?

If your provider brings this up before you ask, you’re in good hands.

4. "Is our network slowing us down?"

Slow tech kills time and focus. Ask:

• Are there recurring slowness issues?

• Do we need better hardware or software?

• What can we tweak to go faster?

Small changes can make a big impact.

5. "Are we still compliant with industry rules?"

Rules change. Fines don’t. Ask:

• Are we still meeting the right standards (HIPAA, PCI, etc.)?

• Have the rules changed?

• Do we need new policies, tools, or training?

Don’t let a rule change turn into a fine.

6. "What should we budget for next quarter?"

Good IT plans ahead. Ask:

• Are any software licenses expiring?

• Is any equipment about to fail?

• Any upcoming upgrades or projects?

Surprises are fun, except when they’re bills.

7. "Are we behind on any trends that could hurt us?"

Falling behind doesn’t just slow you down. It opens you up to risk. Ask:

• Are there tools or best practices we’re missing?

• Are we behind in any security areas?

• What are other companies doing that we aren’t?

• Are there new threats we should worry about?

Your IT partner should keep you ahead of problems, not chasing them.

If your provider can’t give clear answers—or doesn’t offer these check-ins—they might not be doing enough.

Good IT is proactive. Not reactive.
We help businesses like yours spot risks early, avoid waste, and plan smarter.

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