If You’re Only Talking to Your IT Provider When It’s Time to Renew… You’re Doing It Wrong

26 May 2025

Technology isn’t a “set and forget” part of your business. It’s constantly evolving—just like the cyber threats that come with it. That’s why quarterly IT check-ins aren’t optional if you want to stay protected, productive, and ahead of the game.

But here’s the catch: most business owners don’t know what to ask.

So here’s your cheat sheet. These are the questions your IT provider should be ready to answer—clearly, directly, and without tech jargon—every single quarter.

1. Are There Any Vulnerabilities We Need to Fix Right Now?

This isn’t about ticking boxes. It’s about knowing:

Is our antivirus current?

Are any systems unpatched or out of date?
Have there been any red flags or near misses?

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 seatbelts: you don’t think about them until you really need them. Ask:

When was our last full restore test?

Are we using the right backup method (cloud, off-site, hybrid)?
Is everything critical actually being backed up—and stored securely?

You’d be shocked how many businesses think they’re covered... until they’re not.

3. Are Our Employees Following Security Best Practices?

All it takes is one click on the wrong email to bring your business to a halt. Ask:

Any unusual logins or risky user behaviour?

Do we need refresher phishing training?
Is multifactor authentication being used?

Bonus points if your IT provider raises these before you even ask.

4. How Has Our Network Been Performing?

Slow systems kill productivity. Ask:

Any recurring performance issues?

Are we outgrowing current hardware or software?
Can we optimise anything to speed things up?

Sometimes, small changes can have big impact.

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

Rules change. Compliance can’t be a once-a-year check. Ask:

Are we meeting all current requirements?

Has anything changed that affects us?
Do our policies or training need an update?

Fines and penalties aren’t fun. Staying on top of compliance is cheaper than falling behind.

6. What Should We Budget for Next Quarter?

Good IT planning avoids nasty surprises. Ask:

Any licenses expiring soon?

Hardware nearing end-of-life?
Upcoming projects or upgrades we should prepare for?

Proactive budgeting beats emergency spending.

7. Are We Falling Behind on Any Tech or Security Trends?

Tech moves fast. So do the threats. Ask:

Are there tools or best practices we’re not using yet?

Are we lagging behind on performance or security?
What are other businesses our size doing that we’re not?
Are there any new risks we should know about?

Your IT provider should be helping you stay ahead—not just keeping up.

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