What ChatGPT Gets Wrong About LinkedIn Sales Messaging
| June 24, 2025
You open ChatGPT and type:
“Write a LinkedIn message to a VP of Sales about my CRM software.”
In seconds, the AI spits out something polished, professional, and completely useless. It sounds like this:
“Hi [First Name], I hope you’re doing well. I wanted to reach out and introduce myself. We help sales teams streamline their processes, boost productivity, and close more deals. I’d love to set up a quick call to share how we’re helping companies like yours.”
It’s grammatically correct. It’s polite. It even checks the right business buzzword boxes. But it doesn’t work. Because your buyers aren’t ignoring you for bad grammar. They’re ignoring you because your message could’ve been written to anyone. By anyone. And it was. This is where ChatGPT often gets LinkedIn sales messaging wrong, and where sellers need to step in.
The Real Risk of AI-Generated Sales Outreach
AI isn’t the problem. Misusing it is.
When you ask ChatGPT to write messages without proper structure, strategy, or context, it does what it was trained to do: pull from its vast training data and blend the average tone, format, and structure of similar requests. That means:
-Messages sound generic
-Intros are overly polite and empty
-Value props are vague
-CTAs jump too quickly to a call
The result? Messages that feel robotic, irrelevant, and worse, inauthentic. Even your best prospects won’t respond to a message that looks like it was copied from someone else’s inbox. And that’s exactly what most AI-generated messaging feels like: a copy of a copy of a copy.
Where AI Falls Short on LinkedIn
Let’s break down the key misses in AI-generated outreach:
1. It Lacks Personal Context
ChatGPT doesn’t know the person you’re messaging unless you tell it. Without details about their recent post, role, company shift, or shared connection, your message floats in a generic void.
2. It Misses Strategic Timing
AI doesn’t see real-time intent signals. Just because someone is a VP of Sales doesn’t mean now is the right time to reach out. Without triggers like a profile view, post engagement, or new role, it’s just cold outreach disguised in fancy words.
3. It Defaults to Overused Language
ChatGPT often recycles safe, standard phrases: “streamline your process,” “help companies like yours,” “would love to connect.” It sounds like every other message in your prospect’s inbox.
4. It Doesn’t Reflect Your Voice or Value
Even if the message is well-structured, it doesn’t sound like you. It doesn’t connect to your actual offer or how you solve problems differently than everyone else in your space.
So, What’s the Fix? Train the AI, Don’t Let It Lead
ChatGPT is not a messaging expert. It’s a brilliant assistant, when you give it the right instructions. That’s where frameworks like CRISPY™ come in. CRISPY isn’t just a clever acronym, it’s a structure that trains the AI to think like a consultative, permission-based seller who leads with trust and relevance.
Let’s break it down:
CRISPY™: The Framework That Makes ChatGPT Sound Like You
C – Context
What is the reason for reaching out, and what’s happening in the buyer’s world?
Bad prompt:
“Write a message to a VP of Sales about my CRM.”
Better:
“I’m reaching out to a VP of Sales who viewed my profile and just joined a new company. I want to open a conversation about improving pipeline visibility in their first 90 days.”
R – Role
Who should ChatGPT act like? A peer? A consultant? An industry expert? Tell the AI how to show up.
Prompt:
“Act as a peer sales leader who knows what VPs of Sales are dealing with when they step into a new role and want to establish quick wins.”
I – Inspiration
What key insight or positioning should guide the message?
Prompt:
“Base the message around the idea that pipeline visibility is one of the top early priorities for sales leaders and that AI-driven forecasting can help fast-track trust with their CEO.”
S – Scope
What should the message actually include? And what should it avoid?
Prompt:
“Write a short LinkedIn message (under 75 words) that shows relevance, earns the conversation, and ends with a soft next step, not a hard CTA or calendar link.”
P – Prohibitions
What should never appear in the message?
Prompt:
“Avoid generic intros like ‘hope you’re doing well’ or phrases like ‘we help companies like yours.’ Don’t use emojis, don’t pitch, and don’t drop a link.”
Y – You
Instruct the AI to ask clarifying questions before it writes.
Prompt:
“Before writing the message, ask me: What’s the recent trigger? What kind of response do I want? What’s one insight I want to share?”
The Outcome: Messages That Actually Sound Like You
When you use CRISPY, the result isn’t just a better AI message, it’s a smarter seller behind it. Now ChatGPT becomes a tool that supports your strategy, not one that replaces your thinking. It starts asking smarter questions. It remembers to reference context. It reflects your tone, not a stock template. And it starts producing messages that sound human, because they’re built on human insight.
Let’s Compare
Here’s what ChatGPT writes without CRISPY™:
Hi [Name], I came across your profile and was impressed by your background. I’d love to share how our CRM is helping sales teams improve productivity and close more deals. Are you available for a quick call next week?”
Now here’s the CRISPY™ version:
Hi [Name], I saw you recently stepped into the sales leadership role at [Company], congrats. If pipeline visibility is top of mind in these early weeks, I’d be glad to share what’s working for others building momentum quickly. If you are open, let me know I can send a link to my calendar.
Same AI. Very different outcome.
Final Thought: AI Should Make You More You
ChatGPT isn’t here to replace your voice. It’s here to amplify it, but only if you guide it. When you train your AI with the CRISPY™ framework, you stop getting robotic messaging and start getting real conversations. You move from being “another seller” in their inbox to someone worth responding to.
Your prospects can tell when you copy-paste a pitch. They can also tell when you’ve done your homework, understood their world, and showed up with something that matters. Let AI help you say the right thing. But never let it say the same thing as everyone else.
Want better AI-driven sales messaging?
Download the CRISPY Prompt Guide or Book a CRISPY™ Messaging Workshop for Your Team. Let’s teach AI to sound more like you, and less like everyone else.
Want to harness the power of AI and LinkedIn for social selling?
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