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7 Questions You Should Be Asking Your IT Provider Every Quarter (But Probably Aren’t)

May 26, 2025

7 Quarterly IT Questions Every Smart Business Owner Should Be Asking

If you're only talking to your IT provider when it's time to renew your contract, you're doing it wrong.

Technology isn't a "set it and forget it" part of your business; it's a living, breathing system that's always evolving. And so are the threats that come with it. That's why at Dragonfly MSP, we make quarterly IT check-ins non-negotiable. Staying protected, productive, and competitive means making space for regular conversations, not fire drills.

But here's the challenge: Most business owners don't know what to ask.

So, we've created a cheat sheet for you. These are the seven questions your IT provider should be prepared to answer—clearly, honestly, and without tech-speak. If they can't, it might be time to reevaluate your support.

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

This isn't about paranoia—it's about prevention. You need straight answers to questions like:

  • Are antivirus and endpoint protections up to date?

  • Are there any unpatched systems or outdated applications?

  • Have there been any red flags, near-misses, or strange behavior?

At Dragonfly MSP, we provide 24/7/365 device monitoring, vulnerability scanning, and penetration testing to ensure issues are caught early, before they become disasters.

2. 💾 What's the Status of Our Backups? Have They Been Tested?

Backups are your last line of defense, and not all backups are created equal. Ask:

  • When was our last full restore test?

  • Are we using the right strategy—on-prem, cloud, or hybrid?

  • Are all critical files, systems, and SaaS apps being backed up securely?

We offer BDR (Backup & Disaster Recovery), server and endpoint backups, cloud backups for M365/Google Workspace, and regular testing to make sure your data is safe.

3. 🧠 Are All Employees Following Security Best Practices?

One careless click can shut down your entire operation. Make sure your IT partner is watching:

  • Have there been any risky logins or odd behavior?

  • Are your users completing phishing training?

  • Is MFA turned on everywhere that matters?

We include ongoing phishing simulation, training, MFA enforcement, and behavior monitoring as part of our cybersecurity suite.

4. 🚀 How Has Our Network Performance Been? Anything Slowing Us Down?

Slow tech kills momentum. Ask your MSP:

  • Are there any recurring lags or performance issues?

  • Are we outgrowing our hardware or software?

  • Can we optimize any configurations?

We actively monitor your infrastructure, network devices, firewalls, servers, and endpoints to ensure peak performance and uptime.

5. ✅ Are We Still Compliant With HIPAA, PCI-DSS, or Industry Standards?

Compliance isn't just paperwork, it's protection. Ask:

  • Are we meeting our industry's regulatory requirements?

  • Have any policies or standards changed?

  • Do we need updated software, documentation, or training?

With Dragonfly MSP, you get quarterly meetings with a compliance expert, written policies, audit log reviews, and customized reporting to help you stay compliant and audit-readyPackges .

6. 💰 What Should We Be Budgeting For Next Quarter?

Avoid budget shocks by staying informed:

  • Are licenses, warranties, or devices about to expire?

  • Are there any updates we need to prepare for?

  • Any tech purchases or upgrades we should plan ahead for?

We help you proactively manage your roadmap with monthly executive summaries and strategic planning sessions, so you can make smarter financial decisions.

7. ⚠️ What Cybersecurity Trends Are We Falling Behind On?

Staying ahead of cybercriminals means staying current with tools and strategies. Ask:

  • Are there better protections or monitoring systems available?

  • Are we using outdated tech that creates risk?

  • What are our peers doing that we're not?

Our vCISO services include trend reporting, threat intelligence reviews, and executive briefings so you're never left behind.

🚨 Not Having These Conversations? Red Flag.

If your provider can't answer these questions or isn't suggesting quarterly reviews, you're not getting the protection and support your business deserves.

At Dragonfly MSP, we don't wait for things to break. We anticipate, prevent, and protect with a 100% Satisfaction Guarantee, 24/7 monitoring, and a promise that you'll always speak to a tech, not a voicemail.

🔐 Let's Take a Look at Your Setup FREE.

We offer FREE Security Assessments to give you a clear picture of where your business stands, what's working, and what needs fixing before it turns into a costly problem.

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