June 09, 2025
If you only talk to your IT provider when it's time to renew your contract, you're missing the mark.
Technology isn't a "set it and forget it" part of your business. It's always changing, and so are the threats that come with it. That's why having quarterly IT check-ins is essential if you want your business to stay protected, productive, and competitive.
Here's the problem: Most business owners don't know what questions to ask.
So today, 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 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 a full restore was tested?
- Are we using the right backup strategy—off-site, cloud, hybrid?
- Are we backing up the right data?
- Is everything backed up and stored securely?
You'd be surprised how many businesses believe 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 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 any 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?
Regulations change, and so do the rules about how you store and protect data. Ask:
- Are we meeting the standards for our industry?
- Have any requirements changed?
- Do we need to update policies, software, or training?
Fines for noncompliance 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 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 cyber threats 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 similar businesses doing that we're not?
- Are there rising threats we need to watch out for?
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, 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 even faster.
You need someone who isn't just reacting when something breaks but actively working to prevent problems before they happen.
We offer FREE 15-Minute Discovery Call 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 503-966-2538 to book your 15-Minute Discovery Call today!
