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 set once and forget. It's always changing, and so are the risks that come with it. That's why quarterly IT check-ins are essential if you want your business to stay safe, efficient, and competitive. But here's the catch: 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 recent near misses or warning signs?
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 full restore test?
- Are we using the right backup approach? Off-site, cloud, hybrid?
- Are we backing up the right data?
- Is everything backed up and stored securely?
Many businesses believe 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 behavior?
- Do we need another round of phishing training?
- Are employees using multifactor authentication?
Bonus points if your IT provider brings this up before you do—that shows they're paying attention.
4. How Has Our Network Performance Been? Anything Slowing Us Down?
Slow systems mean slow teams and lost productivity (and money). Ask:
- Are there recurring performance problems?
- Are we outgrowing our current hardware or software?
- Can anything be optimized to speed things up?
Even small improvements can have a big impact.
5. Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?
Regulations change, and so do the rules for storing and protecting data. 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 end-of-life?
- Are there upcoming projects we should plan for?
This helps you avoid surprise costs and plan effectively.
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 your IT provider:
- Are there new tools or best practices we're not using yet?
- Are we behind on any security protocols or performance standards?
- What are similar businesses doing that we aren't?
- Are there any emerging threats we should be aware of?
Falling behind on trends doesn't just slow you down, it 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, if they don't even suggest quarterly meetings—you may not be getting the support you need. Technology moves fast. Cyber threats move faster. You need someone who's not just fixing problems after they happen but actively preventing them.
We offer free Security Assessments to help business owners get a clear picture of their technology setup—what's working, what's not, and how to fix issues before they become problems.
Click here or call us at 303-415-2702 to book your 15-Minute Discovery Call
