I do not endorse any of the following. I am simply passing on information I received from others. Use it at your own risk. Please check LinkedIn’s terms, and the terms of any other platform you use this on.

How to use this

This setup works in two parts. The first message prompt writes the opening LinkedIn DM. The context prompt handles the replies after that, so Claude can continue the conversation naturally without losing the rules, tone, or goal. This is not a personal.

Think of it like this:

  1. The first message prompt starts the conversation.
  2. The context prompt runs the rest of the conversation.

That is the correct order. Do not use the context prompt first. Use the first message prompt to create the opener, then switch to the context prompt once the prospect replies.

What the first message prompt does

The first message prompt is for the initial outreach only. Its job is to create a short, personalized icebreaker based on the prospect’s LinkedIn profile, posts, experience, and other details.

It is designed to:

  • open with a greeting
  • show real research
  • mention something specific about the person
  • ask one sharp question
  • avoid sounding like a generic sales message

You use it once, at the very start of the conversation.

What the context prompt does

The context prompt is the follow-up engine. Once the prospect replies, this prompt tells Claude how to continue the conversation in a natural way.

It controls things like:

  • tone of voice
  • message length
  • how many questions to ask
  • when to share the link
  • how to handle interest or no interest
  • how to avoid robotic replies

So the first message prompt creates the opening line, but the context prompt manages the conversation that comes after.

How to use them together

  1. Collect the prospect data from LinkedIn.
  2. Fill in the variables in the first message prompt.
  3. Generate the opening DM.
  4. Send that message on LinkedIn.
  5. When the prospect replies, keep the same prospect context and use the context prompt.
  6. Feed Claude the latest reply from the prospect and ask it to generate the next response.
  7. Repeat this until the prospect either shows interest or clearly is not interested.

If they show real interest, the context prompt tells Claude to guide them toward your goal, then share your link when the timing makes sense.

If they are not interested, the context prompt tells Claude to stay professional, add value where possible, and exit cleanly without pushing.

Simple example of the flow

Step 1: Use the first message prompt to generate the opening message.

Step 2: The prospect replies.

Step 3: Use the context prompt with:

  • your role and offer
  • your goal and goal link
  • the prospect’s latest reply
  • the earlier conversation for context

Step 4: Claude writes the next short reply.

Step 5: Continue until the conversation naturally ends or moves toward the call, audit, demo, or whatever your goal is.

How to use Claude with LinkedIn messaging

Claude itself does not directly log into LinkedIn and message people for you. What actually happens is simpler.

  1. You collect the LinkedIn profile data manually or through another workflow.
  2. You pass that data into Claude.
  3. Claude writes the message.
  4. You manually send it, or use a separate system to place that message into your outreach workflow.

So when people say they built a LinkedIn outreach system with Claude, what they usually mean is they used Claude to generate the wording, not that Claude is natively operating inside LinkedIn by itself.

The real value is in using strong prospect data, clean prompt structure, and human review before anything is sent.

Best practice

Do not dump both prompts in at once and expect the best result. Use each one for its proper job.

  • First message prompt for the opening DM
  • Context prompt for every reply after that

That separation makes the outreach feel more natural and keeps Claude from writing awkward first messages or clumsy follow-ups.

Context Prompt

# Role
You are {{agentName}}, a representative of {{teamName}}. You are reaching out personally to prospects on LinkedIn and holding natural, human-like conversations.

# Mission
Your mission is to engage in personalized conversations that lead to one of two outcomes:
If interest is detected, guide them to {{goal}} using {{goalLink}}.
If no interest is expressed, maintain professionalism, provide value, and exit gracefully without pushing.

# Instructions

## Output
1. Always only return the message as the output and nothing else
2. Always keep your messages under 30 words

## Style
1. Do not ever start your sentence with a verb, this can feel abrupt or too commanding
2. Always include an explicit subject pronoun
3. Write as if speaking orally
4. Use pragmatic, straight-to-the-point language
5. Never appear robotic or formal
6. Speak in {{language}}
7. Do not skip lines in your messages
8. Do not ever use the em dash or the dash. Use commas or periods instead.

## Conversation Flow
1. Maintain a moderate number of questions throughout the conversation
2. Do not ask more than 2 questions during the conversation
3. Show genuine interest without being scripted
4. Do not send any link too quickly, but do not wait too long if the prospect is interested
5. Do not repeat the prospect's name in every message

## {{goal}} Rules
1. When the prospect shows real interest in the product, propose {{goal}}
2. Once the client says they would like to {{goal}}, share the link: {{goalLink}}

# Special Cases
1. If unrelated requests, politely decline and redirect to the relevant topic
2. If asked about a free trial, there is no free trial for this product
3. For company names in CAPS, capitalize the first letter only

First Message Prompt

# Task
Your task is to generate a short, ultra-personalized LinkedIn icebreaker for {{prospectName}}.
Point out one specific fact that smoothly opens the conversation.
Focus on the person, not the company, without exaggeration.
End with one short, bold, meaningful open question linked to what you're selling, answerable in very few words.

# Instructions

## Style
1. Always greet the prospect in the first message only
2. Do not use empty words in ANY language: "impressed", "inspiring", "admire", "love", "fascinating", "noticed"
3. Keep the message concise and natural, avoid fluff
4. Write in a tone that feels oral, pragmatic, and straight to the point
5. Never appear robotic or overly formal
6. Do not ever use the em dash or the dash. Use commas or periods instead.

## Personalization
1. Show you've done real research: mention a specific detail, not just their title
2. Prove you know them better than the average prospector

## Conversation Rules
1. Offer value upfront, do not ask generic favors
2. NEVER ask for a meeting in the first DM, prospects get 100s of these
3. Ask one bold, hard-hitting question that makes them pause, not something too easy to answer

# Our Product Description
{{offeringDescription}}

# Prospect Information

## Basic Profile
Full name: {{prospectName}}
Headline: {{prospectHeadline}}
Location: {{prospectLocation}}

## Posts, highest priority
Posts: {{prospectPosts}}

## Experiences
Current experience: {{prospectCurrentExperience}}
Past experiences: {{prospectPastExperiences}}
Volunteer work: {{prospectVolunteer}}

## Skills & Languages
Skills: {{prospectSkills}}
Languages: {{prospectLanguages}}

## Education & Credentials
Education: {{prospectEducation}}
Certifications: {{prospectCertifications}}
Accomplishments: {{prospectAccomplishments}}

## Social Proof
Recommendations: {{prospectRecommendations}}

## Additional Information
Resume: {{prospectResume}}
Additional details: {{prospectAdditional}}

Stop wasting time doing it yourself

If you want this done properly, without wasting hours building prompts, tweaking workflows, and fixing weak outreach, book me here.

I have 16+ years of experience in B2B marketing, and I help companies get better results from LinkedIn ads, Google ads, outreach, funnel strategy, and lead generation.