9 Questions That Make a Fake “AI Expert” Sweat (Ask Them Before You Sign Anything)

Somewhere out there, right now, a man is updating his LinkedIn headline to “AI Automation Architect | Visionary | Agentic Futurist.”

Last month he sold phone cases.

This week he watched two YouTube tutorials (one at 2x speed), built a chatbot that answers “What are your opening hours?” with a 400-word poem, and is now ready to charge your business $2,500 a month to “transform your operations.”

We call him Superhacker Man. He has a ring light, a course and confidence. What he does not have is a single client who still uses what he built.

The good news: you don’t need to understand technology to catch him. You just need to ask the right questions and listen for the right kind of answer. Real professionals answer with boring, specific details. Superhacker Man answers with vibes.

Here are nine questions. Print them. Bring them to the meeting. Watch him sweat.

1. “What exactly happens, step by step, when a customer places an order?”

You’re not asking about AI. You’re asking whether he understood your business.

A real professional has already asked you this question, probably twice, and drew it on paper. They’ll describe it back to you like a recipe: the message arrives, someone checks stock, the price is confirmed, payment comes in, the order is packed.

Superhacker Man will say: “The AI handles it end to end.”

Handles what, Gerald?

🚩 Red flag: He’s proposing a solution before he’s described your problem. That’s like a doctor prescribing surgery before asking where it hurts.

2. “What happens when it breaks?”

Everything breaks. Websites break. Spreadsheets break. Your cousin’s “temporary” Excel macro from 2019 breaks every time someone sneezes near it.

The real answer sounds like: “You’ll get an alert, here’s who fixes it, here’s how fast, and here’s what you do manually in the meantime.”

The fake answer sounds like: “It won’t break. It’s AI.”

✅ What you want to hear: A specific person, a specific response time, and a backup plan that doesn’t involve praying.

3. “Who owns the accounts?”

This is the most important question on this list, and almost nobody asks it.

Your domain, your website hosting, your WhatsApp Business number, your automation tool, your data: whose name and email are on those accounts?

If the answer is “Don’t worry, I’ll manage all that for you”, worry. Worry a lot. Because the day you stop paying him (or he moves to Canada, or gets into crypto) is the day your business loses its website, its customer list and possibly its phone number.

🚩 Red flag: Any account that runs your business is registered to his email. You should own everything. He should have access, not the keys to the building.

4. “Can you show me something you built that is still running today?”

Not a demo. Not a screenshot. Not a video with dramatic music.

Something live, at a real business, that has been working for at least a few months. Bonus points if you can call that business owner and ask how it’s going.

Superhacker Man’s portfolio is mostly screenshots of other people’s work, a “case study” about a company that doesn’t exist, and a testimonial from someone named “Satisfied Client, USA.”

5. “What will this cost me every month after you’re done?”

The build is the price of the car. The monthly tools are the gas, insurance and the weird noise it makes every winter.

Automation tools, AI subscriptions, hosting and messaging fees all charge every month, and some charge per message or per use. A real professional gives you a list:

Tool	What it does	Monthly cost	Who pays
Automation platform	Moves data between your apps	Fixed or per task	You, on your card
AI service	Writes replies or reads documents	Per use	You, on your card
Hosting	Keeps the system online	Fixed	You, on your card

Superhacker Man says “It’s basically free” and then sends you an invoice for “API credits” that looks like a phone number.

6. “If you disappeared tomorrow, could someone else take over?”

Ask for documentation: a simple written explanation of what was built, where it lives and how it works. It doesn’t need to be pretty. It needs to exist.

A professional expects this question and probably already planned for it. Superhacker Man treats it as an insult, because the honest answer is “No, and that’s the point.”

7. “What would you NOT automate in my business?”

This one is beautiful, because a real expert always has an answer. Some things are cheaper, safer or friendlier done by a human: handling an angry customer, approving a big discount, anything involving your mother-in-law.

If his answer is “Everything can be automated”, he has a hammer and your whole business looks like a nail.

8. “How will we know if it’s working?”

You want a number that matters to you: hours saved per week, orders lost per month, how long customers wait for a reply. Measured before and after.

The fake answer is about engagement, synergy or “the AI learning over time.” Translation: you will never know, and that’s convenient for him.

✅ What you want to hear: “Right now you spend about X hours a week on this. In 30 days, we check it again.” Boring. Measurable. Beautiful.

9. “Can I start with something small?”

A professional is happy to start with one painful task, prove it works, and earn the next one. Small first steps protect both of you.

Superhacker Man needs the 12-month “Total AI Transformation” package, paid upfront, because the offer “expires at midnight.” It has been expiring at midnight since March.

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The cheat sheet

If you only remember one thing, remember this: specific answers are a good sign, vague answers are a warning.

• He talks about your process before his tools → good sign
• You own every account → good sign
• He names a monthly cost list → good sign
• He says “leverage”, “end-to-end”, “agentic” more than twice in one sentence → leave
• His “portfolio” is a robot stock photo → run

And before you hire anyone at all, ask yourself an honest question: could I do this myself in an afternoon with a free tool? Surprisingly often, the answer is yes. That’s what the rest of this blog is for.

Stay sceptical. Stay solvent. See you tomorrow for your next dose.