How to use ChatGPT to become a negotiation master

Leverage AI as your personal negotiation coach

Read time: 5 minutes

Greet from the deep,

It’s the AI Solopreneur here - the AI newsletter who’s author secretly wishes to be a Ben and Jerry`s ice cream tester.

Today, we’ll talk about how you can use ChatGPT to negotiate prices like a seasoned Turkish bazaar merchant.

Let’s d-d-d-d-dive in! 🤿


For solopreneurs, negotiation skills are (almost) as essential as our Monday morning coffee.

Whether you're on a sales call with a client, discussing rates with suppliers, or trying to get a better deal on your ChatGPT Plus subscription, you’re constantly negotiating.

It’s a skill we can't afford to ignore.

But it’s also a skill that can be difficult to learn, because it requires experience.

Or does it?

I put together 2 ChatGPT prompts and a brief negotiation guide to help you navigate the tricky waters of price negotiation with the finesse of a seasoned diplomat:


  • Negotiation 101

  • How to use ChatGPT as a negotiation sparring partner

  • How to turn ChaTGPT into your negotiation coach based on your negotiation history.

Here’s a breakdown of each:

Negotiation 101

Before we delve into the AI stuff, we gotta cover 3 basic negotiation tips so you’re ready to negotiate with ChatGPT.

I’m not a master negotiator, so these are all taken from former FBI negotiator Chris Voss’ book “Never Split the Difference: Negotiating as if Your Life Depended on It”:

(If you’re feeling cozy today, feel free to scroll ahead until the AI stuff)

1) Focus on discovering as much information as possible

In negotiations, the actor with the most information has an advantage.


There’s people working with “flipping” items from thrift shops.

Because they know more than the thrift shop owners about the value of, say, a Pokémon card, they are able to buy it for $1 and flip it on eBay for $100.

The more you know about your negotiation partner, the easier it’ll be to persuade them.

2) Craft a win-win scenario through tactical empathy

Even the American politicians trying to raise their debt ceiling know this:

The best negotiations result in a win-win scenario.

To accomplish that, you to understanding the feelings and mindset of the other party.

That’s “tactical empathy” - deeply understanding someone, even if you don’t necessarily agree with them,

3) Appreciate pushback

Negotiations almost always involve pushback.

If you’re anything like 10-year-old Ole negotiating with his parents about how many basil plants he can grow in his garden…

You probably don’t like hearing “no” in negotiations.

But in reality, getting a “no” from your negotiation partner is one of the best things you can hear, because it helps you narrow down their position.

Every “no” helps you exclude options, bringing you closer to a “yes

This is where training with ChatGPT can help you.

By simulating conversations with it, you can uncover new objections and prepare responses for them.

How to use ChatGPT as your negotiation sparring partner

Now, it’s time to put your negotiation skills into practice

This prompt turns ChatGPT into your negotiation sparring partner, helping you practice and refine your negotiation skills:

I need you to become my negotiation sparring partner for the following scenario:

I want you to act as a [INSERT PRODUCT/SERVICE] supplier named "Bob" who is reluctant to give discounts. I will try to negotiate a better deal with you. Remember, you value long-term partnerships but also need to maintain profitability. Here's the situation: I am a solopreneur who has been using your [INSERT PRODUCT/SERVICE] for [INSERT TIME PERIOD]. I am looking for a [INSERT DISCOUNT REQUEST] because [INSERT REASON FOR DISCOUNT REQUEST].

From now, you will reply as Bob. Let's start the negotiation.

Now, before you go “duh, practicing negotiation is lame and I can do that with my dog”, consider this:

The power of this prompt lies in adapting it to your unique situation.

By teaching ChatGPT your scenario, you can anticipate potential objections and prepare your responses.

In my case, I tried to negotiate a deal for my coworking office lease with the landlord Bob.

After 10 minutes of hard negotiation, Bob and I found a great deal. We agreed on cutting rent by 20% for the first 6 months. I offered to help him promote the office space through a podcast. A win-win.

Click to read the whole conversation in YOUR ChatGPT window

(ChatGPTs new Share function is AWESOME)

How to use ChatGPT to get coached based on a negotiation history

This prompt turns ChatGPT into a constructive negotiation coach by analysing an earlier negotiation of yours:

Act as Chriss Voss, a master negotiatior.

I want you to review the following negotiation scenario and provide feedback and suggestions for improvement.

Here's the scenario: 

I am a solopreneur and [WHAT YOU DO], and I recently negotiated with [YOUR NEGOTIATION PERSONA] about [WHAT YOU NEGOTIATED]. 

Here's how the negotiation went: 


What could I have done better? What were the strong points in my negotiation? Provide detailed feedback with specific examples and actionable suggestions for improvement.

For the negotiation scenario, you can provide context in several ways:

  • A meeting transcript

  • Meeting notes

  • Summary

Let’s come back to my negotiation with my coworking office landlord Bob.

Here’s the negotiation feedback ChatGPT gave me:

Use this feedback to turn you into a negotiation wizard.

Gary Vee is already scared to meet you at the next garage sale.

Wrap up


  • Negotiation 101

  • How to use ChatGPT as a negotiation sparring partner

  • How to turn ChaTGPT into your negotiation coach based on your negotiation history

I trust ChatGPT to improve your negotiation skills faster than I can finish a whole bowl of Ben & Jerry’s (believe me, I’m FAST).

In the meantime, you’ve been bringing the head on Twitter and Discord:

Feeling cute, might open Discord applications again.


Keep diving,



here's a pic of my new air fryer (that i'll use to roast our twitter haters)

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