Most small business owners have no real way to judge whether their IT support is any good. The tech works until it doesn’t, and when something breaks you just hope whoever you call can fix it. That’s a tough spot, because by the time you find out your IT was weak, it’s usually because something already went wrong.
So here are five questions to ask your current IT person, or anyone you’re thinking of hiring. You don’t need to understand the tech. Just watch how confidently and clearly they answer.
1. “When did we last test our backups?”
Notice I didn’t ask if you have backups. Almost everyone says they do. The real question is whether anyone has ever tested restoring from them. A backup that’s never been restored might not work when you need it, and you won’t find out until the worst possible moment. A good IT person tests restores on a schedule and can tell you the last date.
2. “Is MFA turned on everywhere?”
Multi-factor authentication blocks the vast majority of account hacks. If your IT person hasn’t pushed you to turn it on across your email and key systems, that’s a red flag. It’s basic, it’s free, and there’s no good excuse to skip it.
3. “What happens if I get ransomware tomorrow?”
A solid answer sounds like a plan: we restore from backups, here’s roughly how long it takes, here’s what we’d do first. A weak answer is a shrug or a vague “we’d figure it out.” You want the plan to exist before the bad day, not during it.
4. “Who has access to our systems, and how do we cut someone off?”
When an employee leaves, their access should be gone that same day. If nobody is tracking who can get into what, old accounts pile up and turn into open doors. Your IT person should be able to answer this without digging for a week.
5. “Are you watching our systems, or just waiting for me to call?”
There’s a big difference between break-fix, where they show up when something breaks, and managed IT, where they monitor and patch and catch problems before you notice. Break-fix feels cheaper until a small issue you never saw turns into a big outage. You want someone watching.
What this means for you
If your IT person nails these, great, you’re in good hands. If the answers are vague or defensive, that tells you something too. You’re not being difficult by asking. You’re protecting your business.
Want a second opinion?
I’m Jay, a local IT and cybersecurity guy here in South Florida. If you want an honest outside look at where your IT stands, I do free assessments for businesses from Delray Beach to West Palm Beach. No pressure and no sales pitch, just a straight answer. Reach out here.