Behind the Scenes of Great IT Support:

7 Conversation Points that Should Happen Quarterly

If your only touchpoint with your IT provider is when it’s time to renew a contract, you’re missing an opportunity.

Technology doesn’t just run in the background—it needs regular attention to stay secure, efficient, and aligned with your business goals. That’s why quarterly check-ins with your IT provider matter.

Not sure what to bring up? Here’s a helpful list to guide the conversation—clear, practical questions that can surface real issues before they turn into expensive problems. 

  1. Are There Any Security Risks We Should Be Addressing Right Now?

    This isn’t about worst-case scenarios—it’s about awareness. Ask your provider:

  • Is our antivirus current?
  • Are any systems overdue for updates or patches?
  • Have there been any recent warning signs we should know about?

  1. What’s the Status of Our Backups? Have You Tested Them Recently?

    Assuming your backups are working is risky. Confirm:

  • When was the last full restore test?
  • Are we using a solid backup strategy (cloud, local, or hybrid)?
  • Are we backing up the right data—and storing it securely?

  1. Are Our Employees Following Security Best Practices?

    Human error is still the leading cause of breaches. Ask:

  • Any unusual account activity or login attempts?
  • Should we schedule phishing or security awareness training?
  • Are all users set up with multifactor authentication?

  1. Is Anything Slowing Down Our Network or Systems?

    A sluggish system costs more than just time. Check in on:

  • Any recurring performance issues or slowdowns?
  • Are we outgrowing any hardware or software?
  • Can anything be optimized to improve speed?

  1. Are We Still Meeting Our Compliance Requirements?

    Whether it’s HIPAA, PCI-DSS, or something else, regulations evolve. Ask:

  • Are we still meeting current standards?
  • Have any rules or expectations changed recently?
  • Do we need to adjust any policies, software, or staff training?

  1. What Should We Be Planning or Budgeting for Next Quarter?

    Avoid surprise costs. Get clarity on:

  • Any licenses or warranties expiring soon?
  • Hardware nearing end-of-life?
  • Projects or upgrades coming up we should prepare for?

  1. Are We Falling Behind on Tech or Security Trends?

    Staying current is key to staying secure. Ask:

  • Are there tools or practices we should consider adopting?
  • Are we behind in any key areas compared to other small businesses?
  • What new threats should we be aware of?

If You’re Not Having These Conversations, It’s Time to Rethink the Relationship

Quarterly IT check-ins aren’t just about status updates—they’re about strategy, prevention, and keeping your business strong.

If your current provider isn’t initiating these discussions—or can’t give clear, jargon-free answers—it may be time for a second opinion.

Before the next outage or breach, let’s talk. Book a quick, no-pressure 10-minute call to go over your tech setup and priorities.