If your IT provider can’t answer these questions, it’s time to start asking better ones—or start shopping for someone who can.
🚨 Why Quarterly IT Check-Ins Are Nonnegotiable
Let’s cut to the chase: if the only time you talk to your IT provider is when something’s on fire, you’ve already waited too long. IT isn’t a "set it and forget it" checkbox—it’s a living, breathing, constantly evolving part of your business.
Whether you’re a lawyer managing sensitive client data, a CPA handling financial statements, a healthcare practice dealing with PHI, or a small business trying to stay competitive, one overlooked vulnerability could derail your entire operation.
So what should you be asking during those quarterly check-ins? Here’s your cheat sheet—and your wake-up call.
âť“ 1. Are There Any Vulnerabilities We Need To Address Right Now?
This isn’t a hypothetical. It’s the difference between business continuity and business catastrophe.
Ask:
- Are our antivirus and endpoint protection systems fully updated?
- Have any unpatched systems or “shadow IT” risks cropped up?
- Any red flags or near-misses in our logs?
You’re not being paranoid—you’re being prepared.
The 2024 IBM X-Force Threat Intelligence Index noted that unpatched software accounted for over 27% of successful breaches last year. Don’t be a statistic.
💾 2. What’s the Status of Our Backups—and Have You Tested Them Lately?
Backups are like seatbelts. Nobody thinks about them until it’s way too late.
Ask:
- When was the last successful test restore?
- Are we using off-site/cloud/hybrid backups?
- Are all systems and data sets being backed up?
Backups aren’t worth much if you’ve never tested a recovery.
Datto’s 2024 Global State of the Channel Ransomware Report revealed that 68% of small businesses falsely believed their backups were secure—until they failed.
👨‍💻 3. Are All Employees Following Security Best Practices?
Cybersecurity isn’t just a tech issue—it’s a people problem.
Ask:
- Any suspicious logins or compromised credentials lately?
- Are MFA and strong password policies enforced across the board?
- Is it time for a new round of phishing training?
One click on a shady link and your whole network’s toast.
Make sure your provider is tracking user behavior and reinforcing best practices proactively.
⚙️ 4. How Has Our Network Performance Been? Is Anything Slowing Us Down?
Sluggish tech doesn’t just frustrate your team—it costs you real money.
Ask:
- Are we experiencing bottlenecks, lag, or slow file access?
- Are our hardware/software resources keeping up with team demand?
- Is cloud performance optimized for remote/hybrid work?
Your IT setup should accelerate your business—not drag it down.
🏛️ 5. Are We Still Compliant With Our Industry Regulations?
Whether you’re dealing with HIPAA, PCI-DSS, GDPR, FINRA, or ABA rules, staying compliant is critical.
Ask:
- Are we meeting all regulatory standards?
- Have any laws or requirements changed recently?
- Do we need to update policies, software, or employee training?
Compliance is a moving target. Miss it and you could face fines, lawsuits—or worse, lost trust.
đź’° 6. What Should We Be Budgeting For Next Quarter?
IT isn’t just an expense—it’s an investment. But even investments need forecasting.
Ask:
- Any upcoming license renewals?
- Hardware nearing end-of-life?
- Are there strategic upgrades or security improvements we should plan for?
Budgeting beats panic-buying under pressure. Every time.
📉 7. What Trends Are We Behind On That Could Be Holding Us Back (or Putting Us at Risk)?
IT changes fast. Hackers move faster. Your provider should help you stay ahead of both.
Ask:
- What are other firms like ours doing that we aren’t?
- Are there new tools, platforms, or security measures we should explore?
- Are we lagging on any best practices, emerging threats, or benchmarks?
Falling behind in tech means falling behind in business.
🚩 Red Flag: If You’re Not Having These Conversations, You’re Already at Risk
A solid IT partner should come to you with answers—not just wait until you chase them down. If they:
- Can’t give straight, detailed responses to these questions…
- Aren’t proactively offering quarterly reviews…
- Or don’t see cybersecurity as an ongoing strategy…
👉 You’re not being supported. You’re being neglected.
🎯 Ready for Straight Answers—And a Safer Business?
We offer FREE Security Assessments that give business owners a crystal-clear view of:
- What’s working (and what’s not),
- Where your biggest risks are hiding,
- How to get ahead of the threats and protect what matters most.
🛡️ Don’t wait for the next breach or outage.
