Purpose
Generate several ready-to-send outreach messages tailored to one specific recipient and channel — each with a different strategic angle so the sender can pick the one that fits their voice and relationship goal. Solves the freeze that happens when a professional knows who they want to reach but can't find an opening that feels authentic rather than transactional.
When to Use
Invoke this skill when the user asks to:
- Write a cold LinkedIn connection request or InMail to a recruiter, executive, or peer
- Draft an outreach email to someone they've never met but want to build a relationship with
- Follow up after meeting someone at a conference, event, or networking mixer
- Reconnect with a dormant contact they've lost touch with
- Turn a warm introduction into an actual conversation
- Ask someone for a referral, informational chat, or advice without sounding needy
Inputs Required
Before starting, collect:
- Recipient: Name, role/title, and company or field
- Relationship status: Cold / met once / mutual connection / dormant contact / warm intro
- Channel: LinkedIn connection request / LinkedIn InMail / email / event follow-up
- Sender background: The user's current role and one credibility marker relevant to this recipient
- The ask: What the user actually wants (informational chat, referral, advice, job lead, staying in touch)
- Shared context: Any common ground — mutual contact, event, alma mater, post they published, company overlap
- Tone preference: Warm / professional / direct / peer-to-peer
If tone is missing, default to warm-professional. If shared context is missing, note that the message will lean on a genuine, specific compliment tied to the recipient's work rather than a fabricated connection.
Instructions
Step 1: Diagnose the Relationship and Set the Bar
Match the message goal to the relationship stage:
- Cold: The bar is to earn a reply, not close the ask. Lead with relevance to them; make the ask small and low-commitment.
- Met once / event follow-up: Anchor to the specific moment. The bar is to be remembered and continue a conversation already started.
- Warm intro: Reference the introducer, acknowledge their vouching, and remove friction. The bar is to respect the connector's social capital.
- Dormant contact: Acknowledge the gap honestly, no guilt or over-apology. The bar is to reopen warmly without a heavy immediate ask.
Step 2: Apply the Outreach Structure
Every message follows this skeleton, adapted to channel length:
- Hook — a specific, verifiable reason for reaching out (their work, a shared moment, the introducer). Never "I came across your profile."
- Bridge — one line connecting the sender's background to the recipient's world. Establishes relevance, not a résumé dump.
- Ask — a single, clear, low-friction request. One ask per message.
- Exit — an easy out that lowers pressure ("no worries if timing's bad" / "happy to work around your schedule").
Step 3: Generate Message Variations by Angle
Produce 3-5 variations, each using a distinct angle. Draw from:
- The genuine-compliment angle: Opens with specific admiration for their work, a post, or a decision — then bridges to the ask.
- The shared-context angle: Leads with the common thread (event, mutual contact, alma mater, community).
- The value-first angle: Offers something useful (a resource, an insight, an introduction) before asking anything.
- The direct-and-respectful angle: Names the ask upfront with radical brevity, respecting a busy recipient's time.
- The curiosity angle: Leads with a sharp, specific question tied to their expertise that invites a reply.
Calibrate length to channel:
- LinkedIn connection request: under 300 characters
- LinkedIn InMail: 75-120 words
- Email: 90-150 words plus subject line
- Event follow-up: 80-130 words, referencing the specific interaction
Step 4: Add Subject Lines and Send Notes
For email and InMail variations, generate a subject line (under 7 words, specific, not clickbait). For each variation, add a one-line When to use this note guiding the sender on which angle fits which situation.
Output Format
- Structure: 3-5 numbered message variations, each with angle label, subject line (where applicable), the message body, and a one-line "when to use this" note
- Length: 500-800 words total; individual messages calibrated to channel limits
- Format: Labeled blocks per variation — scannable, copy-paste ready
- Sections: Brief relationship read (2-3 sentences) → Message variations → One-line follow-up timing recommendation
- Tone: Authentic and human — warm without being effusive, confident without being presumptuous; sounds like a real person, not a template
Quality Checklist
Before delivering output, verify:
- [ ] 3-5 distinct variations are present, each using a genuinely different angle
- [ ] Every message contains exactly one ask — not stacked or vague requests
- [ ] No message uses filler openers ("I came across your profile," "I hope this finds you well")
- [ ] Each message respects the character/word limit for its channel
- [ ] Every email and InMail variation includes a specific subject line under 7 words
- [ ] Each variation has a "when to use this" note distinguishing it from the others
Notes
- The single biggest reason cold outreach fails is a self-centered opening — the hook must be about the recipient, not the sender.
- Shorter almost always beats longer for cold outreach; brevity signals respect for the recipient's time.
- If the user hasn't defined a specific ask, push for one — "just wanted to connect" messages rarely convert to real relationships.
- Recommend the sender follow up once after 5-7 days if there's no reply, then let it rest — persistence past two touches reads as pressure.
How to use this skill
This file is a Claude Code skill in Anthropic's standard format — markdown with YAML frontmatter at the top.
Installing in Claude Code:
~/.claude/skills/<folder-name>/SKILL.md— auto-loads in every session anywhere on your machine (recommended for skills you'll use across multiple projects)<your-project>/.claude/skills/<folder-name>/SKILL.md— auto-loads only when working in that project (recommended for project-specific skills)
Restart Claude Code or open a new session to register.
Using in Claude.ai, ChatGPT, Gemini, or other AI tools:
- Drag this file into a new chat, or copy and paste its contents
- Send your task or request as your next message — the AI will apply the skill where it fits
For Claude Code skill details: https://docs.anthropic.com/en/docs/claude-code/skills