Hiring AI Help in Naples: 10 Questions to Ask Before You Pay Anyone
By Zechariah Myrick · September 22, 2026 · 12 min read
Before you pay anyone in Naples for AI help, ask ten plain questions: who does the work, can I see something you built, who owns it, what happens if I stop, what do you need from me, how do we talk, what will you not do, how is my data handled, what does done look like, and what is in writing. A good consultant answers all ten without jargon. If they cannot, keep your checkbook closed.
This is for people in Naples and Collier County who have an idea or a business and are about to hire an AI consultant, a freelancer, or an agency for the first time. You are experienced. You have hired plumbers, accountants, and contractors and you know how to judge a person. The trouble with AI work is that you cannot see the plumbing, so the usual instincts need a little help. These questions give them that help.
A story about two roofs
Picture a woman in Naples, call her Ruth, who needed a roof after a storm. Two roofers came out. The first walked the roof, showed her photos of three other houses he had done, wrote a one-page estimate, and told her which part of the job she could skip this year. The second never got on a ladder. He had a folder of glossy pictures, a price that was only good until Friday, and an answer for everything.
You already know which one Ruth hired. You would have hired him too. Now ask yourself: why do so many smart people forget that instinct the moment the word AI is in the conversation? The lesson is this: the plumbing is new, but the way to judge a person has not changed.
Why is hiring AI help different from hiring a contractor?
When a roofer finishes, you can look up. When an AI project finishes, you often cannot tell what you got. Was it built for you, or is it a subscription with your logo on it? Does it keep working if the person disappears? Can you take it somewhere else? Those are the questions a roof never makes you ask, and they are the reason a short conversation up front matters more here.
The good news is that honest people in this field are happy to answer. The questions below are not a test to trip anyone up. They are a way to find out, in twenty minutes, whether you and this person will get along for the next two months.
What are the ten questions to ask any AI consultant?
- 1. Who actually does the work? The person you are talking to, an employee, a subcontractor, or an overseas team? None of those is wrong. You just want to know whose hands are on your project and who to call when something breaks.
- 2. Can I see something you built? Not a slide deck. A real thing you can click, call, or read. If everything they have done is confidential, ask for a small sample built for the conversation.
- 3. Who owns it when it is done? The accounts, the code, the website, the phone number, the written instructions the AI runs on. You should own them or have a clear path to owning them. Get this in writing.
- 4. What happens if I want to stop? Can you walk away after the first phase? Is there a cancellation window? Does the thing keep running, or does it go dark the day you stop paying?
- 5. What do you need from me? A good answer names specific things: a list of your services, your hours, examples of how you talk to customers, an hour a week of your time. A vague answer means they have not thought about your project yet.
- 6. How do we talk, phone or tickets? Some people want a support portal. Most of my Naples neighbors want a phone number and a person who picks up. Ask which you will get and how fast.
- 7. What will you not do? Everyone has limits. An honest consultant will tell you what is outside their skill or outside what they think is safe. Be more nervous of the person who says yes to everything.
- 8. How is my data handled? Where do customer names, messages, and files live? Which AI companies see them? Can they be deleted? You do not need the technical details. You need a plain answer and a person who has clearly thought about it.
- 9. What does done look like? Ask for the test you will run together on the last day. “You call the number, it answers, it texts you a summary” is a finish line. “We will optimize your workflow” is not.
- 10. What is in writing? Scope, price, what is included, what is extra, who owns what, and how either of you ends it. One or two pages is enough. No paper at all is not.
The key that opens one door: the hardest question explained
Question three, who owns it, is the one people skip, because it sounds like lawyer talk. Let me tell it as a story instead.
Picture a man in Naples, call him Gene, who paid someone to set up an AI phone assistant for his charter fishing business. It worked beautifully. Then the person who built it moved to Tampa and stopped answering. The phone number was in the builder’s name. The account that ran the AI was in the builder’s email. The written instructions, the part that told the AI what Gene’s boat could and could not do, lived somewhere Gene had never seen. Gene had paid for a house and been handed a key that only opened the front door. The builder kept the keys to every other room.
When you ask “who owns it,” you are really asking for every key. The phone number, the login, the instructions, the website, the domain name. You should be able to change the password on every one of them the day the project ends, with the builder standing beside you. A good builder will hand you the ring of keys before you ask. Own the keys, not just the door.
What are the red flags?
None of these alone means someone is dishonest. Two or three together mean slow down.
- Pressure. A price that expires Friday. A “limited number of client spots.” Good work does not need a countdown.
- Jargon that does not stop when you ask. If you say “I do not follow” and the explanation gets more technical instead of simpler, that is how the whole project will feel.
- No examples. Nothing to see, nothing to try, nothing to call.
- Asking for your passwords. There are proper ways to give someone access to an account without handing over your password. Anyone who asks for the password itself is either careless or worse. This is the one flag that ends the conversation on its own.
- Big promises about results. Nobody can promise you a number of new customers. They can promise a working test and an honest reading of what it did.
- Everything is a monthly fee, and nothing is yours. Subscriptions can be fine. But if you would own nothing after a year of paying, you should know that going in.
What are the green flags?
- They ask more questions than they answer in the first call, and the questions are about your business, not about AI.
- They suggest a smaller first step than you asked for.
- They tell you at least one thing they would not do, or one thing you do not need yet.
- They explain a technical word the first time they use it, without being asked.
- They put the plain version of the deal in writing before any money moves.
- They are comfortable with you stopping after phase one.
Never give anyone your passwords, not to your email, your bank, your website, or your AI accounts. A legitimate helper will set up separate access, or sit beside you while you type. If a person cannot work without your password, that is the answer to whether you should hire them.
Tricks nobody tells you
You can use AI itself to get ready for hiring AI help. These take a few minutes each with ChatGPT, Claude, or Gemini, and they put you in charge of the conversation before it starts.
- Have the AI play the consultant. Type: “You are an AI consultant trying to sell me a project. I am a 70-year-old retired plumber in Naples. Pitch me, and I will ask you questions.” Practice the ten questions on a machine before you ask a person. You will notice which answers satisfy you and which do not.
- Ask it to argue the other side. Before you sign, paste in the plain summary of the proposal and type: “Give me the five strongest reasons not to do this.” If you cannot answer two of them, you are not ready.
- Translate the proposal. Paste the proposal in and type: “Rewrite this for someone who has never heard the word software. Then list every promise it makes and every promise it avoids making.” The second list is the one to bring to the meeting.
- Write your finish line with it. Type: “Ask me questions until you can write one sentence that describes what I want to be able to do on the last day of this project.” Bring that sentence to every conversation.
- Talk it out with your thumb off the keyboard. Press the microphone on your phone and ramble about what you want for three minutes. Then type: “Turn that into a one-page brief I can hand to a consultant.” I wrote more about this in turning a ChatGPT conversation into a one-page brief.
- Ask what it is not sure about. When the AI explains a term from the proposal, follow up with: “What part of that are you guessing at?” It keeps you from repeating something confidently wrong in the meeting.
- Make the checklist printable. Type: “Turn the ten questions into a one-page checklist with a blank line after each one.” Print it. Take it to the meeting. Write the answers down in ink. Nothing tells a consultant you are serious like a pen.
- Save the good version as a recipe card. Once you have a brief and a checklist you like, save the exact instructions you used in a note. Next time you hire anyone for anything technical, paste the note in first.
Try this in ten minutes
By the end of this you will have a printed sheet in your hand that you can take to any consultant in town, including me.
- Minutes one to three. Open your AI app. Press the microphone and describe, in your own words, what you wish your business or project could do that it cannot do today. Do not edit yourself.
- Minutes four to five. Type: “Turn what I said into one sentence that starts with: On the last day of this project, I want to be able to…” Read it. Change it until it sounds like you.
- Minutes six to eight. Type: “Now make a one-page checklist. Put my finish-line sentence at the top. Below it, list these ten questions with space to write answers.” Paste in the ten questions from this guide.
- Minutes nine to ten. Print it, or email it to yourself. Put it in the folder with the proposal, or on the fridge if there is no proposal yet.
You now have the thing most people walk into these meetings without: a clear finish line and a way to write down what was actually promised.
Freelancer or agency: which is better for a small business?
Neither is better. They are different. An agency has more hands and more process. You may get a project manager, which is helpful, and you may never meet the person who builds your thing, which is not. A freelancer or one-person studio is usually the same person from first call to finish. That is simpler, and it also means you should ask what happens if that one person is sick or on vacation. Ask both what they do about that. A good freelancer has a plan. A good agency can tell you who your actual builder is.
There is also a third option that gets overlooked: doing a small first test yourself with tools you already pay for, then hiring help only for the part that is stuck. I wrote about how to think through that choice in how to choose the right kind of AI project help.
An honest note about asking me these questions
I am an AI consultant in Naples, so you should be a little skeptical of a consultant telling you how to pick one. Fair enough. I answer all ten of these questions myself, in plain words, on the about page and on the work page, so you can check before you call. I am one person, I work by phone, video, or in person in Collier County, and I am independent and not affiliated with OpenAI, Anthropic, xAI, or Google. I will not ask for your passwords. If someone else in town answers these questions better for your situation, hire them. There is plenty of good work to go around.
What I would do first
- Write your finish line in one sentence. Before you talk to anyone, decide what you want to be able to do on the last day. “Customers can book online and I get a text.” Bring that sentence to every conversation. It keeps you in charge.
- Talk to two people, not one. Not to bargain. To hear two different plain explanations of the same problem. You will learn more from the difference than from either one alone.
- Ask for the smallest first phase they would sell you. Then ask what you would own at the end of it. If both answers are clear and you like the person, you have probably found your help.
When to call someone
Picture a woman in Naples, call her Marian, with a proposal on her kitchen table. She has read it four times. She understands about half of it. She could sign, she could throw it away, or she could spend thirty minutes on the phone with someone who reads these every week and ask what she is actually being offered. Which of those three costs the least? The lesson: a second opinion is cheapest before the check clears.
Call when you have the finish line written and you are not sure who to trust with it. Call when you already paid someone and you cannot tell what you got. Call when a proposal is sitting on your desk and you want a second opinion before signing. Those are good reasons to spend half an hour on the phone with a person who does this every week.
If you want to start with a conversation rather than a contract, Call (239) 544-6990 or send me a note. Tell me what you want to be able to do on the last day. If I am not the right fit, I will say so. You might also find what to expect from a first AI idea session useful before you pick up the phone.