🐙 How to use ChatGPT as your sales coach

Learn how to sell like a professional

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Greet from the deep,

It’s Ole from the AI Solopreneur here.

Today, I’m bringing you hotter sales tips than a jalapeño in a sauna.


Selling is one of the most fundamental skills of succeeding as a solopreneur.

Master it, and you can print money with almost any product.

But the problem is:

Getting good at sales takes time and reps.

Especially in the beginning, I had no confidence in how to handle sales conversations in the DMs.

That’s why I built you a ChatGPT sales conversation coach that helps you sell in your direct messages (DMs).

By the end of this email, you’ll know all the DM-selling basics you need to land your first $1,000+ customer.


Let’s dive in!


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The Only 5 Sales Principles You Need To Close Your First Client

If I had to start all over again, I’d be able to get my first client with just 5 sales tips:

1. Educate, Don't Sell

Amateurs ask prospects if they want to buy their stuff.

Professionals give away free consulting to educate customers on why they need their service.

For example, if you are a Twitter ghostwriter, give your prospect feedback on their past tweets to demonstrate expertise.

Don’t think about selling as selling.

Rather, think about it as educating and giving your prospects so much value that THEY ask you what you offer.

Because of the reciprocity bias, we don’t like feeling indebted to anyone - if you give enough value, your prospects will eventually get uncomfortable about not giving you something back.

2. The Personal Touch

Include a personalised compliment every time you send out a cold outreach sales message.


Because it shows you’ve done your homework.

For example, if 2 website designer reached out to you, who would you respond to:

  1. “Hey, your website looks great I’d love to make it even better”

  2. “Hey, I noticed that the menu bar on your website doesn’t appear on X and Y page, and it’s probably worsening your conversion rate and sales. You can solve this by doing XYZ.”

Of course you’d go with the second designer because they:

Educated you on a problem you didn’t know you have

Also told you why it’s an urgent problem you need to solve

Also offered a solution to the urgent problem

…all in just 2 sentences!

3. Casual Friday, Every Day

Make your DMs feel like you’re sitting next to your prospect sipping a chilled mojito at a beach bar.

Not too informal, but friendly and relaxed.

Remember, you're not proposing marriage, just a casual chat.

This makes the prospect feel more comfortable and makes you sound more experienced (amateurs always try to be overly formal).

4. Strike the deal with confidence

After you’ve consulted the prospect for free and showed them your offer, it’s time to seal the deal.

Ideally, you do this on a call.

Amateurs collect money like this:

“Can you pay me $2000 please?”

Don’t ever ask for money - this puts the power in your prospects hands.

Instead, say:

“I’ll send you the $2000 invoice now”

That way, you sound as if you’ve done it a hundred times before and as if the price is non-negotiable.

5. What to do if the prospect doesn’t agree on the price

If your prospect doesn’t agree on your initial price - that’s fine.

You can either let it be, or you can lower your price, and downsell yourself.

But here’s the challenge:

If you don’t downsell properly, you kill your credibility and lose the deal.

To lower your price in a legitimate way, you must always give a reason for why you decrease the price.

For example:

“Sure, I’d be happy to lower the price to $3,000 if you wouldn’t mind introducing me to 2-3 people who might be interested in my service to cover my costs”


“Sure, I can do it for $2,500 if you wouldn’t mind me asking a few extra questions about [INSERT SOMETHING THEY KNOW] during our collaboration”

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Prompt: The Sales Conversation Coach

Now that you know the 5 basics of selling in the DMs, I want to supply you with a sales coach that’ll help you make better decisions when selling.

Especially when it’s about getting the first client, it’s easy to feel nervous about what to reply, and that’s why I found getting a second (robot) opinion insanely helpful.

This prompt gives you advice whenever you feel struck in a sales conversation:

I want you to act as a professional sales coach and advise me on replies an ongoing conversation with a prospect.

For context, I offer [WHAT YOU OFFER]

My goal is to close the client, no matter what.

Here's the chat history:


Please output 4 things:

1) A pre-written reply optimized for my goal you'd do in my tone of voice as you can see in the chat history (I'm the person offering a service)
2) An explanation as to why you chose this reply
3) Any further considerations I should keep in mind before replying*
4) A general sentiment analysis of the prospect 


This prompt analyses your chat history and gives you 4 things:

  1. A pre-written reply in your tone of voice (for the objective of closing the client)

  2. An explanation for why the sales coach recommends this reply

  3. Any further considerations you should keep in mind

  4. A general sentiment analysis of how interested the prospect is in your product

Here’s an example of how it coached me (acting as an imaginary web designer):

Wrap up


  • The 5 only sales principles you need to get your first client

  • How to downsell when the prospect thinks your price is too high

  • How to use The Sales Conversation Coach to get DM sales advice

Mastering sales is something I neglected for too long. The second my mindset shifted, I started makign more money.

It sounds cringe but, its true.

To wrap it up, It wouldn’t be a Saturday Deep Dive without me sending you pics from a random restaurant.

Today it’s gonna be some goold old Schnitzel!

Enjoy your weekend.

Keep diving,


P.S. Send me reply and tell me what you’re up to this weekend.
I want to know more about my readers :)

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