If your only conversation with your IT provider happens when you're renewing your contract, your business could be missing out on critical protection, performance upgrades, and long-term planning.

Technology isn't a "set it and forget it" part of your operations. It's constantly evolving, and so are the risks that come with it. Regular check-ins, ideally once per quarter, can keep your business secure, productive, and prepared for what's next.

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

That's why we put together this quarterly IT check-in cheat sheet. These are the questions your provider should be able to answer—clearly, without tech jargon or vague promises.

1. Patch Gaps: Are There Any Vulnerabilities We Need to Fix?

This is about more than running antivirus scans. Ask your IT provider:

  • Are our antivirus and endpoint protections fully up to date?
  • Do we have any unpatched systems or outdated software?
  • Have there been any recent security alerts, red flags, or near misses?
  • Are we running regular vulnerability scans or penetration testing?

Proactive vulnerability management helps prevent downtime and keeps threats from slipping through the cracks.

2. Backup Health: Are Our Backups Current and Tested?

Backups are like seatbelts: You don't think about them until you need them. At your check-in, ask:

  • When was our last full restore test?
  • Are we using the best-fit strategy (local, cloud, hybrid)?
  • Are we backing up the correct data and storing it securely?
  • How quickly can we recover in the event of data loss?

It's not enough to have backups. They need to be working, secure, and recoverable.

3. Workforce Readiness: Are Employees Following Security Best Practices?

Even the best security setup can fail if people do not follow protocols. Ask:

  • Have there been any unusual login patterns or risky behavior?
  • Are we due for a phishing simulation or training refresh?
  • Is everyone using multifactor authentication (MFA)?
  • Are remote workers following secure access guidelines?

If your IT provider is tracking user behavior and flagging risks before you ask, that's a great sign.

4. System Speed: How's Our Network and Device Performance?

Technology should help your team move faster—not slow them down. During your check-in, ask:

  • Are there any recurring issues or complaints about performance?
  • Are we outgrowing any hardware, software, or bandwidth?
  • Are we monitoring uptime, latency, and system loads?
  • Is there anything we can optimize to improve speed?

Even minor performance tweaks can boost productivity across the board.

5. Data Responsibility: Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?

If your business handles sensitive data, staying current with compliance standards is non-negotiable. Ask:

  • Are we meeting our industry's data protection standards?
  • Have any regulations or requirements changed recently?
  • Do we need to update any policies, training, or software?
  • Are there new state or local data privacy laws we should address?

Compliance lapses can be costly. Staying informed helps you avoid surprise audits and penalties.

6. Smart Planning: What Should We Budget For Next Quarter?

Surprises in tech budgets can derail your plans. Get ahead by asking:

  • Do we have any upcoming license renewals or subscriptions that need attention?
  • Is any equipment nearing end-of-life?
  • Are there upgrades, migrations, or new tools we should plan for?
  • Are there any cost-saving opportunities we're not using?

Budget transparency enables you to plan proactively rather than reactively.

7. Staying Ahead: What Trends or Threats Should Be on Our Radar?

Technology changes fast—and cybercriminals move even quicker. Use this check-in to ask:

  • Are there emerging threats or vulnerabilities we need to address?
  • Are there security protocols we're lagging on?
  • What are similar businesses doing that we might learn from?
  • Are there new tools (like automation or AI-based monitoring) we should explore?

A great IT partner will help you lead, not just keep up.

Not Having These Conversations Yet? Let's Fix That.

Quarterly IT check-ins aren't just a best practice—they're essential for maintaining security, ensuring compliance, and enhancing productivity. If your provider isn't addressing these topics, it may be time for a second opinion.

We offer a no-obligation Security Assessment to help business owners assess their current tech setup—what's working, what's not, and how to improve it before minor issues become costly problems.

Click here to book your free assessment.

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Need help? Contact The MacGuys+ at 763-331-6227 

Top-notch IT support for Mac-based businesses in Minneapolis, St. Paul, Twin Cities Metro, Western WI, and beyond. Enjoy seamless nationwide co-managed Mac IT support for a flexible work-anywhere experience.