5 Questions to Ask the Person Who Manages Your Business's IT

If someone else manages your website, your systems, or your data — a freelancer, a small agency, a "guy who set everything up" — there's a good chance you've never actually asked them these questions. In our research, this came up constantly: business owners assuming their provider "has it covered," without ever checking what that actually means.

That's not a criticism of your provider. It's just worth knowing, plainly, what you're actually paying for.

1. "Who else has access to our systems, and how do we remove someone if they leave?"
If the answer is vague, that's worth a follow-up — access that nobody's tracking is access nobody can revoke when it matters.

2. "Do we have backups, and have they ever actually been tested?"
A backup that's never been restored is a backup nobody's sure actually works. Ask when the last real restore test happened.

3. "If something goes wrong — a hack, a data leak — what happens in the first hour?"
You're not looking for a technical answer. You're looking for whether there's a plan at all, and whether you'd be told immediately or found out later.

4. "Is multi-factor authentication actually turned on for our accounts, or just available?"
There's a real difference between a platform offering MFA and someone actually switching it on. Ask them to show you, not just tell you.

5. "Where exactly is our customer data stored, and who can see it?"
A one-sentence, specific answer is a good sign. A shrug or "it's all handled" is worth pushing on gently.

None of these questions require you to understand the technical details yourself — they're designed so you can tell, from how confidently and specifically they're answered, whether your provider actually has this handled or has just been assuming so, the same way you might have been.