For professional service firms across Chicagoland — from Naperville to the North Shore — technology isn’t just a tool. It’s the backbone of your operations.
But if your only interaction with your IT provider is when it’s time to renew the contract, you’re missing critical opportunities to protect and grow your business.
Technology evolves fast. So do cyberthreats. That’s why quarterly IT check-ins aren’t just a nice-to-have — they’re essential.
Not sure what to ask during those check-ins? Here’s your Chicagoland Business Owner’s IT Health Checklist — no jargon, no fluff, just the questions that matter.
1. Are There Any Vulnerabilities We Need to Fix Right Now?
This isn’t about paranoia — it’s about preparation.
- Is our antivirus current?
- Are there any unpatched systems?
- Have there been any red flags or near misses?
You deserve straight answers, not vague reassurances.
2. What’s the Status of Our Backups — and Have You Tested Them?
Backups are like insurance: useless if they don’t work when you need them.
- When was our last full restore test?
- Are we using the right backup strategy (cloud, off-site, hybrid)?
- Are we backing up the right data — and is it secure?
Many Chicagoland businesses think they’re covered… until they’re not.
3. Are Our Employees Following Security Best Practices?
One wrong click can bring your entire network down.
- Any suspicious logins or risky behavior?
- Do we need a refresher on phishing training?
- Is multifactor authentication in place?
A proactive IT partner will bring this up before you even ask.
4. Is Our Network Slowing Us Down?
Slow systems = lost productivity = lost revenue.
- Are there recurring performance issues?
- Are we outgrowing our current hardware or software?
- Can we optimize anything to speed things up?
Even small tweaks can make a big difference in your team’s efficiency.
5. Are We Still Compliant With Industry Regulations?
Whether you’re in legal, healthcare, finance, or consulting — compliance matters.
- Are we meeting HIPAA, PCI-DSS, or other industry standards?
- Have any regulations changed?
- Do we need to update policies, software, or training?
Fines for noncompliance aren’t just costly — they’re reputation killers.
6. What Should We Be Budgeting for Next Quarter?
Good IT is proactive, not reactive.
- Any licenses expiring?
- Any aging equipment we should replace?
- Any upcoming projects we should plan for?
Avoid surprise expenses and plan like a pro.
7. Are We Falling Behind on IT or Cybersecurity Trends?
Technology doesn’t stand still — and neither do cybercriminals.
- Are there new tools or best practices we’re missing?
- Are we lagging behind in security or performance?
- What are other Chicagoland firms our size doing that we’re not?
Falling behind doesn’t just slow you down — it leaves you exposed.
Not Having These Conversations? 🚩 That’s a Red Flag.
If your IT provider isn’t offering quarterly check-ins — or can’t clearly answer these questions — it might be time for a second opinion.
We help Chicagoland business owners get a clear, honest look at their IT setup — what’s working, what’s not, and how to fix it before it becomes a crisis.
👉 Click here to book your FREE Security Assessment
Let’s make sure your business is protected, productive, and ready for what’s next.
