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 nonnegotiable 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, we’re giving you a cheat sheet. These are the questions your IT provider should be ready to answer every single quarter – no tech-speak, no vague promises, just straight answers that keep your business running smoothly.

1. Are There Any Vulnerabilities We Need To Address Right Now?

This isn’t just about checking boxes. You need to know:

• Is our antivirus up-to-date?
• Are there unpatched systems?
• Have we had any near misses or red flags lately?

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, 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 things?
• Is everything being backed up and stored securely?

You’d be shocked how many businesses think they’re backed up…until they’re not.

3. Are All Employees Following Security Best Practices?

It only takes one team member clicking the wrong link to bring the whole network down. 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 ask. That’s how you know they’re watching.

4. How Has Our Network Performance Been? Anything Slowing Us Down?

Slow systems = slow teams = 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 tweaks can make a big difference.

5. Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?

Regulations change. 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 aren’t cheap. Stay ahead of them.

6. What Should We Be Budgeting For Next Quarter?

Good IT is proactive. Ask:

• Are there any software licenses expiring?
• Any equipment nearing the end of its life?
• Any upcoming projects we should be planning for?

This helps you avoid surprise expenses and plan like a pro.

7. What Trends In IT Or Cybersecurity Are We Behind On That Are Making Us Slower Or More Vulnerable?

Technology doesn’t stand still – and neither do cybercriminals. Ask your IT provider:

• Are there new tools or best practices we’re not using yet?
• Are we lagging behind in any security protocols or performance benchmarks?
• What are other businesses our size doing that we’re not?
• Are there any rising threats that we need to be more cautious of?

Falling behind on emerging trends doesn’t just slow you down – it leaves you exposed. A great IT partner will keep you ahead of the curve, not playing catch-up.

You AREN’T Having These Conversations? Red Flag

If your IT provider doesn’t have clear answers to these questions – or worse, if they aren’t offering to meet with you quarterly in the first place – you might not be getting the support you need.

Technology changes fast. Cyberthreats 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 to book your assessment today!

TOSS C3 is the trusted Cyber Technology and Security provider located in Massachusetts specialized in serving law firms, libraries, local governments, healthcare providers and the Fortune 1000 throughout the USA.