7 Questions South Florida Business Owners Should Be Asking Their IT Provider Every Quarter (But Probably Aren’t)

7 Questions South Florida Business Owners Should Be Asking Their IT Provider Every Quarter (But Probably Aren’t)
If the only time you talk to your IT provider is when you’re renewing a contract—or when something breaks—you’re not getting the value you deserve.
Your business technology is not a “set it and forget it” system. It's evolving constantly, and so are the cybersecurity threats targeting companies across Palm Beach, the Treasure Coast, and beyond.
That’s why quarterly IT check-ins are essential—not optional—for any small to mid-sized business that wants to stay secure, efficient, and ahead of the curve.
At Capstone IT, we meet with our South Florida clients regularly to review exactly what’s working, what needs attention, and how to plan for what’s next. And if you don’t know what to ask during those meetings, here’s your cheat sheet.

1. Are There Any Security Vulnerabilities We Need to Fix Right Now?Don’t wait for a breach to find out your systems weren’t protected.

Ask your IT provider:
  • Is our antivirus software current?
  • Are there unpatched systems or devices?
  • Have there been any near-misses or suspicious activity?
Proactive cybersecurity means identifying and addressing red flags before they become threats.

2. What’s the Status of Our Backups – and Have They Been Tested Recently?

Backups only help if they actually work.
Ask:
  • When was the last time a full restore was tested?
  • Are we using the right strategy (off-site, cloud, hybrid)?
  • Are we backing up the most critical data and systems?
  • Is everything stored securely?
Many South Florida businesses believe they’re backed up—until they’re hit with ransomware or server failure, and find out otherwise.

3. Are Employees Following Security Best Practices?

Your people are your biggest asset—and sometimes your weakest security link.
Ask:
  • Are there any reports of risky behavior or login anomalies?
  • Do we need another round of phishing training?
  • Is multifactor authentication (MFA) in place for all critical systems?
Your IT partner should be monitoring these behaviors and proactively guiding your team.

4. How’s Our Network Performance? Anything Slowing Us Down?

Slow networks kill productivity—and frustrate your team.
Ask:
  • Are we seeing any recurring performance issues?
  • Are our systems outdated or nearing capacity?
  • Can we optimize anything to run more efficiently?
If your business is growing, your IT infrastructure needs to grow with it.

5. Are We Still Compliant With Industry Regulations?

Whether it’s HIPAA, PCI-DSS, GDPR, or local requirements, compliance is a moving target.
Ask:
  • Are we meeting current standards for our industry?
  • Have any regulations or requirements changed?
  • Do we need to update policies, tools, or employee training?
Noncompliance can lead to major fines, lawsuits, and loss of client trust—especially in regulated industries like legal, healthcare, and finance.

6. What Should We Be Budgeting for Next Quarter?

Proactive planning avoids surprise costs.
Ask:
  • Are there licenses, software, or services expiring soon?
  • Is any equipment approaching end-of-life?
  • Are there IT projects we should begin scoping?
Capstone IT helps businesses from Jupiter to Boca Raton plan for future needs so tech never becomes a bottleneck.

7. What IT or Cybersecurity Trends Should We Be Paying Attention To?

Falling behind in technology can make your business more vulnerable and less competitive.
Ask:
  • Are we missing out on tools or services other businesses are using?
  • Are there gaps in our cybersecurity posture?
  • Are there rising threats that we should be aware of?
  • How can we improve performance or automation?
A forward-thinking IT partner like Capstone IT will help you stay ahead of the curve, not just catch up to it.

🚩 Not Having These Conversations? Big Red Flag.

If your IT company isn’t offering these quarterly reviews—or can’t provide straight answers to these questions—it may be time to reevaluate your provider.
Technology is moving fast. Cyber threats in South Florida are evolving daily.
Don’t settle for reactive IT support that only shows up when something’s broken. Partner with a local IT team that works proactively to keep your business running securely and smoothly, every day of the year.

✅ Schedule Your FREE Technology Business Consultation Today

Let’s uncover the gaps in your current IT strategy—and show you how we can fix them before they impact your bottom line.