June 09, 2025
If you're only communicating with your IT provider when it's time to renew your contract, you're missing the mark.
Technology is not something you set up once and forget about. It constantly changes, and so do the threats that come with it. That's why having quarterly IT check-ins is essential if you want your business to remain secure, efficient, and competitive.
The problem is, most business owners don't know what questions to ask.
To help, here's a list of questions your IT provider should be prepared to answer every quarter—no jargon, no vague responses, just clear answers that help keep your business running smoothly.
1. Are There Any Vulnerabilities We Need To Address Right Now?
This goes beyond ticking boxes. You need to find out:
- Is our antivirus software current?
- Are there any systems that haven't been patched?
- Have there been any recent warning signs or near misses?
Being cautious here isn't paranoia—it's preparation.
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 best backup strategy—off-site, cloud, or hybrid?
- Are we backing up the right data?
- Is all backup data 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 employee clicking a bad link to compromise the whole network. Ask:
- Have there been any unusual logins or risky behaviors?
- Do we need another round of phishing training?
- Is multifactor authentication in use by all employees?
If your IT provider brings this up before you do, that's a good sign they're vigilant.
4. How Has Our Network Performance Been? Anything Slowing Us Down?
Slow systems mean slow work and lost productivity. Ask:
- Are there recurring performance problems?
- Are we outgrowing our current hardware or software?
- Can anything be optimized to improve speed?
Even small improvements can have a big impact.
5. Are We Still Compliant?
Regulations change frequently, affecting how you protect and store data. Ask:
- Are we meeting all industry standards?
- Have any compliance requirements recently changed?
- Do we need to update policies, software, or training?
Noncompliance fines can be costly, so staying ahead is crucial.
6. What Should We Be Budgeting For Next Quarter?
Good IT management 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 prepare for?
This helps avoid surprise expenses and keeps your budget on track.
7. What Trends In IT Or Cybersecurity Are We Behind On That Are Making Us Slower Or More Vulnerable?
Technology and cyber threats evolve constantly. Ask:
- Are there new tools or best practices we haven't adopted yet?
- Are we falling behind in security protocols or performance?
- What are other businesses our size doing that we're not?
- Are there emerging threats we should be aware of?
Falling behind on trends doesn't just slow you down—it exposes you to risk. 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 your business needs.
Technology moves fast. Cyber threats move faster.
You need someone who doesn't just fix problems after they happen but actively works to prevent them in the first place.
We offer a FREE Initial Consultation 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 turns into a problem.
Click here or give us a call at 312-564-5446 to book your Initial Consultation today!
