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 threats that come with it. That's why quarterly IT check-ins are essential if you want your business to stay protected, efficient, 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 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 current?
- 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 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 assume 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?
If your IT provider brings this up before you ask, 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 slow teams and lost productivity. Ask:
- Are there recurring performance problems?
- Are we outgrowing our hardware or software?
- Is there anything we can optimize to speed things up?
Small improvements can have a big impact.
5. Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?
Regulations and data protection rules change frequently. Ask:
- Are we meeting industry standards?
- Have any requirements changed?
- 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 expiring?
- 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 never 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 standards?
- What are other similar businesses doing that we're not?
- 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 strong 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 even suggest quarterly meetings—you may not be getting the support you need.
Technology evolves fast. Cyber threats move faster.
You need someone who's not just fixing problems after they happen but actively working to prevent them.
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 (541) 726-7775 to book your 15-Minute Discovery Call
