Owners of established businesses get sold to constantly by people promising systems, funnels, automation and AI. It does not matter much whether you run a firm, a clinic, an agency or a coaching practice: most of you have no reliable way to tell a competent provider from a confident one, because the vocabulary is unfamiliar and the claims are unverifiable.
So here are the questions I would ask. I sell this kind of work, which means you should apply every one of them to me, and that is the point. A checklist its author would fail is not a checklist, it is an advertisement.
On evidence
Where did that number come from? Any statistic on their website or in their pitch. Ask what was measured, when, and for whom. A provider who can name the table, the date and the client is a different proposition from one who says a percentage with confidence and moves on.
Was the measurement defined before the work started, or found afterwards? This is the question most reported marketing results cannot survive. Searching data after the fact for a number that supports the argument produces true statistics and false conclusions, which is why I think a result has to be measured forward or it is not evidence.
What were the inputs? A result produced from a list of twelve hundred past contacts is not available to somebody with forty. The ratio might transfer. The absolute number never does. A provider quoting an outcome without its input is setting you up to fail against a benchmark you were never able to hit.
Can I speak to a client for whom it did not work? Nobody expects a yes. How they handle the question is the information.
On ownership and exit
If I leave in six months, what do I keep? Get this in writing, specifically. The content, the data, the automations, the domain, the account logins. It is common for an owner to discover the assets were built inside the provider's account.
Can I export everything, and in what format? Ask for a sample export before signing, not a promise of one.
Whose name is on the accounts? Your advertising account, your domain, your email sending domain, your database. These should be yours with them granted access, never the reverse. This is the single most common way businesses get trapped, and it is invisible until you try to leave.
What happens if you stop trading? A one-person provider, which most of us are, is a real continuity risk. A decent answer exists. No answer at all is the finding.
On scope
What will you not do? A provider who does everything has not thought about it. Anyone serious can name the work they turn away.
Who does the work? Specifically. If the person selling is not the person building, ask who is and whether you will speak to them.
How much of my time will this take? Almost every system requires the owner's input to be worth anything, because the material and the judgment are yours. A provider claiming near-zero involvement from you is describing something generic, which will produce generic results.
What is the smallest useful version, and what does it cost? Anyone who can only sell you the whole thing has not diagnosed anything. There should be a first piece that stands on its own and fixes one part of the business, say the Engage stage, where interested people try to act and quietly give up.
On AI specifically
Whose words come out the other end? If anything writes in your voice, ask what it is built from. Your material and your language, or a house style with your name on it. The second is worse than nothing, because it is generic writing wearing your identity. If you have never written down how you sound, do that before anyone builds anything that talks for you.
What runs without my approval, and can I change that? The answer should be a setting you control per message type, not a fixed property of their system.
What does it never touch? Any provider worth hiring has a category they will not automate. If they do not, they have not thought about your industry. I have my own list of where I let AI near the business and where I do not, and you should expect the same from anyone you hire.
Where does my client data go, and what is it used for? Which vendors, which countries, and whether anything is retained or used for training. If you are in a regulated profession, this answer has to satisfy your professional body, not just you.
The two questions that tell you most
What would you tell me not to do? A good answer names something you were already considering and explains why it will not work for your situation. A bad answer is a mild caution followed by a pivot back to the pitch.
What is the honest downside of working with you? Everyone has one. Mine is that I am one person, so I am a continuity risk, and I am selective about who I take on which makes me slower to start than an agency would be. A provider who cannot answer this either has not examined their own work or is not going to tell you the truth about anything else either.
My own smallest useful version is the Revenue Acceleration Review. Hold it to every question on this page.
Questions owners ask
How much should this kind of work cost?
It varies enormously and price alone tells you very little. What is more diagnostic is whether the provider priced against a defined outcome or against a number of hours, and whether they were willing to scope a smaller first piece. Be more suspicious of a very low price than a high one: the work still has to be done by somebody, and a low price usually means a template.
Should I hire an agency or an individual?
An agency gives you continuity and process, and you will often not speak to the person doing the work. An individual gives you their judgment and carries real key-person risk. Ask the ownership and exit questions above of both, because both fail those questions with roughly equal frequency.
What if I do not understand what they are proposing?
That is information, and it is about them rather than you. Anyone competent can explain what they are building in terms of what changes in your week. Persistent jargon after a direct request for plain language is usually a sign that the substance is thinner than the vocabulary.
Can I just do this myself?
Some of it, yes, and a decent provider will tell you which parts. Writing down what each client is dealing with, keeping a commitment log, and following up on the people who went quiet are all things you or your team can do this week for free. Get those working first; you will hire better afterwards, because you will know what is actually missing.