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. 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.
The problem is, most business owners don't know what to ask.
So here's a quick guide. 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 just a checklist. You need to know:
- Is our antivirus current?
- Are there any unpatched systems?
- Have there been any recent warnings or close calls?
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 method—off-site, cloud, or hybrid?
- Are we backing up everything important?
- Is the backup data stored securely?
Many businesses think they're backed up until disaster strikes.
3. Are All Employees Following Security Best Practices?
One wrong click can compromise your entire network. Ask:
- Have there been any unusual logins or risky activities?
- Do we need more phishing training?
- Is multifactor authentication in use?
If your IT provider brings this up before you do, that's a good sign they're on top of things.
4. How Has Our Network Performance Been? Anything Slowing Us Down?
Slow systems mean lost productivity and money. Ask:
- Are there recurring performance problems?
- Are we outgrowing our hardware or software?
- Can anything be optimized to improve speed?
Small improvements can have a big impact.
5. Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?
Regulations change, and so do data protection rules. Ask:
- Are we meeting current industry standards?
- Have any compliance requirements changed?
- Do we need updated 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 expiring soon?
- 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 evolve constantly. Ask:
- Are there new tools or best practices we haven't adopted yet?
- Are we falling behind in security protocols or performance standards?
- What are similar businesses doing that we aren't?
- Are there new threats we should be more 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, doesn't want to meet with you quarterly—you may not be getting the support your business needs.
Technology moves fast. Cyber threats move faster.
You need someone who's not just reacting when something breaks but actively working to prevent the break in the first place.
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 turns into a problem.
Click here or call us at 608-416-2400 to book your 10-Minute Discovery Call today!
