The 6 Things Every CEO Should Ask Their IT Provider

CEOs ask a lot of great questions. What’s our runway? How do we scale this team? Why is marketing spending so much on coffee? But when it comes to IT, most CEOs just want to know, “Is it working?” If emails are sending and files are saving, the general assumption is that everything’s fine.

Until it’s not.

That’s when the real questions start. Why didn’t we have backups? Why weren’t we alerted sooner? Why do we have five different tools doing the same thing? Why do we pay for all this and still feel behind?

Here’s the thing—most IT providers aren’t shy about talking tech. But they rarely volunteer what you should be asking. They’ll answer whatever you bring up, but they’re not going to sit you down and say, “Hey, want to know how your disaster recovery plan’s actually just vibes?” That part’s on you.

The good news? You don’t have to become a tech expert. You just need to ask smarter questions—the kind that uncover what’s really going on behind the scenes. The kind that get past the shiny dashboards and nice reports and into the messy details that actually matter.

We’re not talking about obscure acronyms or server specs. We’re talking about the kind of stuff that impacts your business if it goes sideways. Stuff like accountability, clarity, and whether someone is actively watching the things you assume are being watched.

Let’s go through six questions that don’t get asked nearly enough—and why they matter more than “How fast is our internet?”

First up: “Who is actually responsible when something breaks?”
It sounds simple, but you’d be surprised how many IT setups are built on the idea that someone will handle it—just not sure who. Maybe it's the help desk. Maybe it's your “strategic account manager.” Maybe it's nobody, and you're about to find out the hard way. If your provider can’t give you a clear, direct answer (preferably with names, not departments), that’s a red flag disguised as ambiguity.

Next: “What’s the plan if we lose access to everything?”
And we mean everything. Not a file. Not an app. We’re talking full blackout. Ransomware, cloud outage, catastrophic mistake—that kind of day. If the answer includes “well, first we’d look into…” you’re in trouble. You want a provider who can talk through recovery time, communication plans, data priorities, and how your team would keep operating in the meantime—without making it up as they go.

Another one: “How often do we review access control?”
Because Todd from finance who quit eight months ago? Still has admin rights. And that shared password your ops team uses? Probably hasn’t been changed since pre-pandemic days. You don’t need a fancy audit every week, but there should be a regular, scheduled review of who has access to what. And someone should be losing access every time they walk out the door—not months later when someone stumbles across their account.

Also: “Are we getting what we’re paying for?”
There’s often a shiny PDF involved here. Charts, uptime stats, maybe a vague roadmap. But dig deeper. Ask what’s actually been done lately. Ask how your current tools are being used, and if there’s overlap, waste, or just plain outdated stuff sitting in your stack. Ask what they’ve proactively recommended to save you money or improve something. If it’s been radio silence for months, you’re not getting a strategy—you’re getting shelfware.

Then there’s the big one: “Are we truly secure… or just checking boxes?”
It’s easy to say you’ve got antivirus, backups, and MFA. But how often are those backups tested? Is MFA rolled out to everyone? Are those alerts being reviewed by humans or just sent to a folder no one opens? There’s a difference between compliance and actual protection. Make sure your IT provider knows which one you care about.

Finally: “When was the last time you told us no?”
This one stings a little. But a good IT partner isn’t afraid to say, “That’s not a good idea,” or “That tool isn’t secure,” or “That request doesn’t align with your bigger goals.” If they’re just nodding along and collecting checks, you’re not being challenged. And that’s a missed opportunity for growth—and for avoiding preventable headaches.

Conclusion

CEOs don’t need to know how to write PowerShell scripts or configure VLANs. But they do need to know which questions will uncover the gaps that silently grow into chaos. You can’t lead well if you’re only looking at the surface.

These six questions aren’t about catching your IT provider off guard. They’re about getting clarity, building trust, and making sure your business is actually supported— not just technically, but strategically.

If you haven’t asked these yet, now’s a good time to start. You might be surprised by what comes out of the conversation. And if your provider seems caught off guard… well, that tells you something too.