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 risks that come with it. That's why having quarterly IT check-ins is essential if you want your business to stay secure, 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 prepared 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 just about ticking boxes. You need to know:
- Is our antivirus up to date?
- 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 right backup strategy? Off-site, cloud, or hybrid?
- Are we backing up the right data?
- Is everything backed up and stored securely?
Many businesses think 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 means 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 any 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 change, and so do the rules about data storage and protection. Ask:
- Are we meeting the standards for our industry?
- Have any requirements changed?
- Do we need to update policies, software, or training?
Noncompliance fines aren't cheap. Stay ahead of them.
6. What Should We Be Budgeting For Next Quarter?
Good IT is proactive. Ask:
- Are any software licenses expiring soon?
- 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 your IT provider:
- Are there new tools or best practices we're not using yet?
- Are we falling behind in any security protocols or performance standards?
- What are other businesses our size doing that we're not?
- Are there any emerging threats we should be cautious about?
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 offer to meet with you quarterly—you might not be getting the support you need. Technology changes fast. Cyber threats move faster. You need someone who doesn't just fix problems after they happen but works to prevent them in the first place.
We offer free Security Assessments to help business owners like you get a clear picture of your tech setup—what's working, what's not, and how to fix issues before they become problems.
Click here or call us at 781-837-0069 to book your 15-Minute Discovery Call
