7 Smart IT Questions Every Business Should Ask Regularly (But Often Don’t)

If your only interaction with your IT provider is when something breaks—or when it’s time to renew a contract—your business may be missing out.

Technology is always changing. And along with those changes come new challenges businesses must be ready for. That’s why it’s essential to have regular conversations with your IT team—ideally every quarter. These check-ins can uncover hidden problems, strengthen security, and make sure your business stays one step ahead.

Not sure what to ask? Consider asking these seven key questions during your next IT review to keep your systems strong and secure.

1. Do We Have Any Security Gaps Right Now?

Problems can go unnoticed unless someone is actively looking for them. Start by asking if there are any weak spots in your systems. Are all updates and patches current? Have there been any warning signs of attempted attacks or unusual activity? Being cautious doesn’t mean overreacting—it means staying prepared.

2. Are Our Backups Working, and Have They Been Tested?

Backups are your safety net. But just having them isn’t enough—they need to be tested to make sure they’ll work when you need them most. Ask when the last test was done, what data is being backed up, and where it's stored. Some companies believe their backups are working fine—until they try to recover data and realize otherwise.

3. Are Our Employees Following Cybersecurity Guidelines?

People are often the easiest way into a network for hackers. One wrong click on a bad link can cause serious damage. Ask if there’s been any risky behavior or strange login attempts. Is your team using strong passwords and multi-factor authentication? Has anyone skipped cybersecurity training? Learn more about The Importance of Cyber Security Training and why employees should attend it.

4. Is Anything Slowing Down Our Network or Devices?

When your technology lags, productivity drops—and that can hurt your bottom line. Find out if your devices or software are showing signs of aging. Ask about ways to speed things up, improve reliability, or reduce downtime. Even minor fixes can help your team work faster and smarter.

5. Are We Still Meeting Industry Rules and Requirements?

If your business handles sensitive data, you likely have compliance rules to follow—such as HIPAA, PCI-DSS, or others. These rules change over time, and your systems and policies need to keep up. Ask if your current setup still checks all the right boxes and what needs to be updated.

6. What IT Costs or Upgrades Should We Plan for Next?

Technology isn’t just an expense—it’s part of your strategy. Ask about licenses, hardware replacements, or software renewals that are coming up. Planning ahead keeps your budget under control and avoids last-minute surprises.

7. Are There New Threats or Tools We Should Know About?

Cybercriminals are always trying new tricks, and technology is always evolving. Your IT provider should help you stay on top of both. Ask if there are any new risks you should be watching or new tools that could help your business work better or stay safer.

No Answers? That’s a Warning Sign

If your IT provider can’t answer these questions—or isn’t offering to meet with you regularly—it may be time to rethink who’s managing your technology.

Let’s discuss what to do more than fix problems.