June 09, 2025
If you're only talking to your IT provider when you renew your contract, you're doing it wrong. Technology isn't a "set it and forget it" part of your business. It's constantly evolving, 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.
But here's the thing: most business owners don't know what to ask.
So today, here's a cheat sheet. These are the questions your IT provider should be ready to answer every single quarter—no tech jargon, no vague promises, just straightforward 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 hardly 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, 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're not.
3. Are All Employees Following Security Best Practices?
It only takes one employee clicking the wrong link to bring down 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 proactively. That means they're watching out for you.
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 any hardware or software?
- Is there anything we can optimize to speed things up?
Sometimes small tweaks 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 recently?
- Do we need to update policies, software, or training?
Noncompliance fines are 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 the end of its life?
- Are there upcoming projects we should plan for?
This helps avoid surprise expenses and keeps your budgeting on track.
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 yet using?
- Are we lagging behind in any security protocols or performance benchmarks?
- What are other businesses our size doing that we aren't?
- Are any new threats emerging that 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 you clear answers to these questions—or worse, if they don't even offer to meet with you quarterly—you might not be getting the support you need. Technology changes fast. Cyberthreats move faster. You need a partner who's not just reacting to problems but actively working to prevent them.
We offer FREE Security Assessments to help business owners like you get a clear view of your tech setup—what's working, what's not, and how to fix issues before they become problems.
Click here or call us at 720-449-3379 to book your 15-Minute Discovery Call
