Here are the questions your IT/cybersecurity provider should always be ready and willing to answer.

Your IT provider isn’t just a service vendor — they’re a core part of your risk strategy and business continuity plan. But unless you’re asking the right questions, you’ll never know if they’re keeping up or just coasting. These questions aren’t just helpful — they’re essential. If your IT partner can’t answer them clearly and confidently, it’s time to rethink who’s watching your digital front door.

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 non-negotiable if you want your business to stay protected, productive and competitive. But, most business owners don’t know what to ask.

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

 

2. What’s the status of our backups? Have they been tested lately?

  • When is the last time a full restore was tested?
  • Are we using the right backup strategy for us? Off-site? Cloud? Hybrid?
  • Are we backing up the right data?
  • Is everything being backed up and stored securely?

 

3. Are my employees following best security practices?

  • Have there been any unusual logins or risky behavior?
  • Do we need another round of phishing training?
  • Have we required MFA for all staff?

 

4. How has our network performance been? Anything slowing us down?

  • Are you seeing recurring performance issues?
  • Are we outgrowing our hardware/software?
  • Is there anything we can optimize to speed things up?

 

5. Are we still compliant with [HIPAA, PCI-DSS, GDPR, etc.]?

  • Are we meeting the standards for our industry?
  • Have requirements changed?
  • Do we need to update policies, software, or training?

 

6. What should we be budgeting for next quarter?

  • Are any of our software licenses expiring?
  • Any equipment or operating systems nearing end-of-life?
  • Any upcoming projects we should be planning for?

 

7. What IT or cybersecurity trends are we behind on that are making us slower or more vulnerable?

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

 

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.

***Would You Be Against Scheduling 15 Minutes?***
Let's set a time to discuss how we can support your IT lead. 
Contact Angela Jamerson at (630) 406-8969 x576 or ajamerson@datalinkmsp.com

Dedicated to your cybersecurity.