Let me ask you something straight:
When’s the last time you sat down with your IT provider and actually talked shop not invoices, not renewals, but your business, your systems, your people?
If the answer is “last year when the contract came up,” then partner, we’ve got a problem.
Technology isn’t like a forklift you can park and forget. It moves fast and the stuff coming after your business? It moves even faster.
Threats are evolving. Compliance rules are shifting. And your systems? They’re aging, one patch and workaround at a time.
That’s why quarterly IT check-ins aren’t just a good idea, they’re your insurance policy. For uptime. For security. For sanity.
But here’s the thing: Most business owners don’t know what to ask.
So today, we’re giving you a cheat sheet. These are the questions your IT provider should be ready to answer every single quarter – no tech-speak, no vague promises, just straight answers that keep your business running smoothly.
1. “What’s Broken or About to Be?”
Don’t just ask if things seem okay. Ask:
- Are we missing any critical patches?
- Have there been any close calls lately?
- Is our antivirus up to date, or just installed?
This isn’t being paranoid, it’s called being prepared. If something’s on fire under the hood, better to spot the smoke before the blaze.
2. “Are Our Backups Real... or Just Hopeful?”
Here’s the thing about backups: Everybody thinks they’ve got them. But ask yourself:
- When’s the last time we tested a full restore?
- Are we backing up the right stuff? (I’ve seen folks back up empty folders.)
- Is it off-site? Cloud-based? Air-gapped? Encrypted?
Your backups are only as good as the day you need them. And by then? It’s too late to double-check.
3. “Is My Team a Security Liability?”
Hard truth: It only takes one person clicking a bad link to bring your whole operation to a standstill. You need to ask:
- Have there been weird login attempts?
- Are we using multi-factor authentication across the board?
- Do we need to run phishing training again?
If your IT team shrugs this off, that’s your red flag. Because good providers are watching people as much as systems.
4. “What’s Slowing Us Down?”
Slow tech doesn’t just annoy people. It costs you money. Ask:
- Are any of our systems bottlenecked?
- Are we outgrowing our hardware?
- Could small upgrades speed things up?
Even shaving a few seconds off each task adds up over a day, a week, a quarter. That’s not convenience. That’s profitability.
5. “Are We Still Compliant?”
Regulators don’t care if you “didn’t know.” If you’re in healthcare, defense, energy or just collect customer info, you’ve got standards to meet. Ask:
- Have rules changed since last quarter?
- Are our policies and training up to date?
- Could we pass an audit today, cold?
Getting blindsided by noncompliance can wipe out more than your budget. It can wipe out your credibility.
6. “What Should I Be Budgeting for Next?”
Surprises are great for birthdays. Not for IT. Ask:
- Any licenses or renewals coming up?
- Any gear we should be retiring?
- Any system upgrades we should be planning?
Forecasting tech costs means you stay in control, not scrambling to find $12,000 for a server upgrade two weeks before it croaks.
7. “What’s Everyone Else Doing That We’re Not?”
You don’t need the fanciest tools, but you sure as heck don’t want to be the only one without a fire extinguisher when things get hot. Ask:
- Are there best practices we’re missing?
- What tools or protocols are now standard in our industry?
- Any rising threats on the radar we’re exposed to?
Good IT pros keep an ear to the ground. They’ll spot what’s coming before it knocks on your front door.
Not Having These Conversations? That’s the Real Problem.
If your IT provider isn’t asking these questions or worse, can’t answer them clearly, you’re flying blind. And in today’s world? That’s not just risky. That’s reckless.
Because here’s the deal: Tech doesn’t break on a schedule. Hackers don’t wait for renewals. And when things go wrong, you need a team that’s already two steps ahead, not someone flipping through a manual while the plant grinds to a halt.
Let’s Get You the Right Questions and the Right Answers
If it’s been a while since anyone’s taken a hard look at your systems or if you’re hearing more tech buzzwords than plain answers, we can help.
We offer FREE Security Assessments for businesses like yours. No sales pitch. No pressure. Just a clear, honest look at what’s solid, what’s shaky, and what you can fix before it breaks. You’re already doing the hard part, running a business. Let’s make sure the tech behind it isn’t the thing that takes it down.
Click here to book your assessment today!
