How I negotiate with the help of AI, part 1: setting it up

A special edition. For the next five days I am doing one thing: negotiating with the help of AI, a different deal each day.

It started with a car. I am leasing one right now, and late last week I posted the short version: I did the homework with AI before I emailed a single dealer, and walked in already knowing the numbers. That post got more questions than almost anything I have written, and they were all the same one. How, exactly?

This week I want to show you how, deeper than a single post can go. Not the idea of it, the actual nuts and bolts: the steps, the exact prompts, what I used, and where it earns its keep in real life.

Today is part one: setting it up — the three steps that decide the deal before you talk to anyone.

Most deals are decided before you talk to anyone

Think about how a negotiation actually goes. You show up tired, on their clock, with a few hours of weekend research against someone who does this every single day. The car, the contractor, the renewal, the offer letter. The other side knows the real numbers and you are guessing. By the time you are at the table, the outcome is mostly set, and it was set before you said a word.

That is the part AI is genuinely good at. Not the charm, not the closing. The homework. The boring, time-eating legwork that decides the deal before anyone speaks — the part you never have the hours to do properly. Hand that off, and you arrive as the prepared one for once.

The goal here is not to over-rely on AI. The goal is to be as well-informed as possible before anyone starts talking. AI does the research and does not get tired. You make every call that matters.

Here is the method I used on the lease, in six steps. It works the same on a contractor bid, a medical bill, or a job offer. The deal changes. The method does not.

Step 1: Name what you actually need

Start by telling AI the real constraints, not the wish list. Give it specs: model or vehicle type, size, equipment level, budget, the things that are not negotiable, the things you will not live with. Let it shortlist the real options and tell you what holds its value and what people regret.

This works best when you are not locked into a specific vehicle yet. You show up with a list of real candidates instead of a gut feeling and a price sticker. That said, it works just as well if you already know the model and trim. Tell AI what you are targeting and it will tell you whether the deal in front of you is actually good, or just dressed to look that way.

“I am in the market for [vehicle type or specific model]. My constraints: [budget], [size and equipment needs], [dealbreakers]. Shortlist the best real options for me. For each, tell me what it typically costs, what holds its value, and the one thing people regret. Ask me whatever you need to narrow it down.”

Step 2: Find who can actually deal

Not every seller can move on price, and the highest rating online is not the same as the one who will cut you a deal. Have AI tell you who in your area carries the thing, who moves real volume, and who to skip.

“For [the thing] in [my city or zip], tell me which dealers, contractors, or providers actually carry it and move real volume, and which to avoid. I want the ones who can actually cut a deal, not just the highest rating on Google.”

Step 3: Get to a real person

The form on the website goes to whoever answers forms. The person who can say yes is someone else.

For a car dealer, start with the Internet sales department. The Internet manager handles online inquiries, works off a different script than the showroom floor, and can move on numbers. For other deals: the fleet manager, the office manager, whoever handles volume without a walk-in script.

Have AI find that person’s direct contact so your first message lands with someone who can actually act on it. I would not reach out to the owner. Internet manager first.

“Find the direct contact for the Internet manager or fleet manager at [each dealer or business]. Not the general sales line or web form. Give me a name and an email address where you can.”

That is the setup half. Three steps that happen before you send a single message: what you want, who has it, and who can actually move on it.

Tomorrow I will cover the second half — building the assistant, pulling the real numbers, and sending the email. Including whether and how to let AI run the back-and-forth without you.

Want the full setup, step by step, with all six prompts? Comment or DM “playbook” and I will send it.

Part 2 is here: how to build the assistant, get the numbers, and send the email.

Strictly non-clinical. Nothing on this site is medical advice, legal advice, or financial advice, and I do not post about patient care. For a binding document, use a qualified professional.