article · QUESTIONS TO ASK BEFORE HIRING AI HELP
Ask These Before YouSign Anything.
Every owner I meet in The Valley who has been burned once was burned the same way. Nobody lied to them. They were handed answers that sounded fine and could not be checked. These twelve questions are the ones that cannot be answered vaguely.
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01 · the first question to ask
The first question to ask.
Who will actually be doing the work, and will I be talking to them.
Ask it first, in those words, and listen for a name. In most engagements that go wrong, the senior person you met is the person who sold it, and the account moves to somebody junior the week after you sign.
02 · questions about the work
Questions about the work itself.
Which of my processes would you automate first, and why that one
You are listening for a reason grounded in what the process costs you, not for whichever one demos best.
What will you not automate here
A senior answer has exclusions in it. Anyone who says everything is a candidate has not done this in a real business.
What happens the first time it gets something wrong
There should already be an answer, and it should involve a human approval step in front of anything that sends, charges or deletes.
What does month one look like, week by week
Ask for calendar dates and named deliverables. If the plan is a phase with a Roman numeral in front of it, ask again.
03 · questions about ownership
Questions about ownership and access.
This is where the quiet damage happens. An engagement can end with the work having been fine and you still holding nothing.
Whose name is on the accounts
The domain, the hosting, the analytics, the ad accounts, the Google Business Profile and the automations. All of them should be yours, opened under your email.
What do I take with me if I leave
The right answer is everything, exported, with nothing to rebuild. Anything less is a switching cost designed into the relationship.
Where do my credentials live
A vault with revocable access per connection, not a shared spreadsheet and not a settings field on somebody's laptop.
Is anything you build only maintainable by you
Ask it plainly. A build nobody else can pick up is a lock on you, whether or not it was meant as one.
04 · questions about proof
Questions about proof.
Two questions, and they are the ones most likely to change the temperature of the meeting.
Show me something you shipped that I can open right now
Not a slide of a dashboard. A URL. Live work, with a client's name on it and a date attached.
How will I check, in month three, that something happened in month two
The answer you want is a dated record you can open yourself. A monthly report that does not link to last month's is not a record, it is a document.
05 · questions about price
Questions about the money.
What is the number, and what is not in it
Software subscriptions, ad budget and third party fees should be named as yours and paid to the vendors directly. Nobody should be marking up your tools.
What does it cost to stop
Look for three months, then month to month with written notice. A term you cannot exit is a term you will be inside the day you want out.
06 · ai vendor red flags
Answers that should end the meeting.
| what you hear | What it usually means | What to ask instead |
|---|---|---|
| We guarantee a top position | A promise nobody controls, including Google itself | What will you guarantee that you actually own |
| Our proprietary AI platform | A reseller wrapper on tools you could hold in your own name | Which vendors is this built on, and whose account are they in |
| You will get a full report every month | A document, not a record | Can I open the change log myself, without asking you |
| We handle everything, do not worry about it | You will not be able to check anything | Show me where a shipped item gets dated |
| The price depends on your revenue | You are being priced on what you can bear | What is the list price, and is it the same for everyone |
| We need admin on all your accounts to start | Access convenience, structured as a hold on you | What is the least access that lets you begin |
07 · my answers
My own answers.
08 · hiring ai help questions
Hiring AI help questions.