7 Questions You Should Be Asking Your IT Provider During Your Quarterly IT Check-In

If the only time you talk to your IT provider is when you renew your contract, you're leaving your business exposed.

Technology isn’t a “set it and forget it” part of your operations. It’s constantly evolving — and so are the threats. That’s why quarterly IT check-ins aren’t optional if you want to stay secure, productive, and competitive.

But what should you ask? Most business owners don’t know where to start.

Here’s your quarterly IT check-in cheat sheet — seven essential questions your IT provider should be able to answer clearly, confidently, and without tech-speak.

Why a Quarterly IT Check-In Matters More Than You Think

1. Are There Any Immediate Vulnerabilities We Need to Address?

This is about more than running antivirus scans. You need to know:

• Is our antivirus software current and effective?

• Are any systems missing critical patches?

• Have there been any near-miss incidents or suspicious activity?

You're not being paranoid — you're being proactive.

2. What’s the Status of Our Backups — and Have You Tested Them Recently?

Backups are like seat belts: you don’t think about them until it’s too late.

• When was our last full restore test?

• Are we using the right backup strategy (cloud, on-site, or hybrid)?

• Are we backing up the right systems and data?

• Is everything encrypted and stored securely?

Many companies think they’re covered — until disaster strikes.

3. Are Our Employees Following Security Best Practices?

All it takes is one careless click to bring a business down.

• Any unusual logins or risky behaviors detected?

• Is it time for another round of phishing or security awareness training?

• Are employees using multi-factor authentication?

If your IT provider brings this up before you do, you’ve got a winner.

4. How Is Our Network Performing?

A sluggish system drains productivity — and profits.

• Are there ongoing performance issues we’re not addressing?

• Are we outgrowing current hardware or software?

• What can we optimize to speed things up?

Sometimes a few small tweaks make a big difference.

5. Are We Still Compliant with [HIPAA, PCI-DSS, GDPR, etc.]?

Regulations evolve — and noncompliance can be costly.

• Are we still meeting the latest compliance standards?

• Have any rules or requirements changed?

• Do we need to update policies, software, or employee training?

Stay ahead of compliance to avoid fines, breaches, and headaches.

6. What Should We Be Budgeting for Next Quarter?

Good IT is proactive — and that includes financial planning.

• Are there any licenses or subscriptions expiring?

• Is any equipment nearing end-of-life?

• Are there upcoming upgrades or security projects we should prep for?

This helps you avoid nasty surprises and stay on track.

7. Are We Behind on Any IT or Cybersecurity Trends?

Falling behind doesn’t just slow you down — it makes you vulnerable.

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

• Are our security protocols up to modern standards?

• What are similar-sized businesses doing differently?

• Are there emerging threats we need to prepare for?

The right IT partner keeps you ahead of the curve — not scrambling to catch up.

🚩 Not Having These Conversations? That’s a Red Flag.

If your provider doesn’t offer clear answers — or isn’t even scheduling regular check-ins — it may be time to rethink your support.

Technology changes fast. Cyber threats move faster.

You deserve an IT partner who doesn't just fix problems — they prevent them.

✅ Get a Free Security Assessment

We offer complimentary Security Assessments to help you understand your current tech landscape: what’s working, what’s not, and what you can do to improve.

📅 Click here to schedule your free assessment today.