June 09, 2025
If you only talk to your IT provider when it's time to renew your contract, you're missing the point. Technology isn't something you can just set up and forget. It's always changing, and so are the threats that come with it. That's why quarterly IT check-ins are essential if you want your business to stay secure, efficient, and competitive.
The problem is most business owners don't know what questions to ask. So, here's a cheat sheet. These are the questions your IT provider should be ready to answer every quarter—no jargon, no vague promises, just clear answers that keep your business running smoothly.
1. Are There Any Vulnerabilities We Need To Address Right Now?
This isn't about ticking boxes. You need to know:
- Is our antivirus current?
- Are there any unpatched systems?
- Have we had any close calls or warning signs recently?
You're not being paranoid; you're being prepared.
2. What's The Status Of Our Backups? And Have You Tested Them Lately?
Backups are like seat belts—you don't think about them until you really need them. Ask:
- When was the last time a full restore was tested?
- Are we using the best backup strategy? Off-site, cloud, hybrid?
- Are we backing up the right data?
- Is everything backed up and stored securely?
Many businesses assume they're backed up—until they find out they're not.
3. Are All Employees Following Security Best Practices?
It only takes one person clicking the wrong link to compromise the entire network. Ask:
- Have there been any unusual logins or risky behaviors?
- Do we need another round of phishing training?
- Are employees using multifactor authentication?
If your IT provider brings this up before you do, that's a good sign they're paying attention.
4. How Has Our Network Performance Been? Anything Slowing Us Down?
Slow systems mean slow teams, which means lost productivity and money. Ask:
- Are there recurring performance issues?
- Are we outgrowing our current hardware or software?
- Is there anything we can optimize to speed things up?
Even small improvements can make a big difference.
5. Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?
Regulations and data protection rules change. Ask:
- Are we meeting industry standards?
- Have any requirements changed recently?
- Do we need to update policies, software, or training?
Noncompliance fines can be costly. Stay ahead of them.
6. What Should We Be Budgeting For Next Quarter?
Good IT is proactive. Ask:
- Are any software licenses about to expire?
- Is any equipment nearing the end of its life?
- Are there upcoming projects we should plan for?
This helps you avoid surprise expenses and budget wisely.
7. What Trends In IT Or Cybersecurity Are We Behind On That Are Making Us Slower Or More Vulnerable?
Technology and cyber threats keep evolving. Ask:
- Are there new tools or best practices we're not using yet?
- Are we falling behind in security protocols or performance standards?
- What are other businesses our size doing that we aren't?
- Are there new threats we should be aware of?
Falling behind not only slows you down but also leaves you exposed. A great IT partner keeps you ahead, not catching up.
You Aren't Having These Conversations? Red Flag
If your IT provider can't give clear answers to these questions—or worse, doesn't offer to meet quarterly—you might not be getting the support you need. Technology changes fast, and cyber threats move even faster. You need someone who's not just fixing problems after they happen but actively working to prevent them.
We offer FREE Security Assessments to help business owners like you get a clear picture of their tech setup—what's working, what's not, and how to fix issues before they become problems.
Click here or call us at 847-348-3381 to book your 15-Minute Discovery Call
