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 up once and forget about. 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 protected, productive, 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 technical 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 near misses 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 you tested a full restore?
- Are we using the right backup strategy—off-site, cloud, or hybrid?
- Are we backing up the right data?
- Is everything being backed up and stored securely?
You'd be surprised how 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 team member clicking the wrong link to compromise the whole 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 and lost productivity (and money). Ask:
- Are there recurring performance issues?
- Are we outgrowing our 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 storing and protecting data. Ask:
- Are we meeting industry standards?
- 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?
- Is any equipment nearing the end of its life?
- Are there upcoming projects we should plan for?
This helps you avoid surprise expenses and plan effectively.
7. What Trends In IT Or Cybersecurity Are We Behind On That Are Making Us Slower Or More Vulnerable?
Technology and cybercriminals don't stand still. 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 benchmarks?
- What are other businesses our size doing that we're not?
- Are there rising threats we need to be more cautious about?
Falling behind on trends doesn't just slow you down; it leaves you exposed. A great IT partner keeps you ahead of the curve, not playing catch-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 cyberthreats move faster. You need someone who's not just reacting when something breaks but actively working to prevent problems before they happen.
We offer free security assessments to help business owners like you get a clear view of their tech setup—what's working, what's not, and how to fix it before it becomes a problem.
Click here or call us at 760-770-5200 to book your Quick and Easy Call
