Purpose
Generate ready-to-send outreach messages to senior executives that earn a reply — built on a genuine, specific connection point, a single low-friction ask, and a respectful tone calibrated to the recipient's seniority. Solves the "I don't know how to word this without sounding like every other cold message" problem for job seekers, students, and professionals reaching up the org chart.
When to Use
Invoke this skill when the user asks to:
- Write a cold email or LinkedIn message to a senior executive
- Request an informational interview with someone more senior
- Ask an executive to be a mentor or advisor
- Reach out to a founder, VP, or C-level leader for networking
- Turn a warm intro or shared connection into a first message
- Follow up after an executive didn't reply to a first outreach
Inputs Required
Before starting, collect:
- Your background: Current role/status (e.g., MBA candidate, marketing analyst, career switcher) in 1–2 sentences
- Target executive: Name, title, company, and seniority level
- The ask: Mentoring / informational interview / networking intro / advice on a specific decision
- Connection point: Shared alma mater, mutual contact, their published work, a company milestone, a talk they gave — anything specific and true
- Channel: Email / LinkedIn / warm intro forward
- What you admire or want to learn: The specific reason you chose this person, not a generic one
- Your relevant credibility (optional): One accomplishment or context that makes you worth a reply
If channel is missing, default to LinkedIn for a first cold contact and email for a warm-intro follow-up. If no credibility point is given, lead entirely with the connection point and the specificity of the ask.
Instructions
Step 1: Diagnose the Ask and Set the Friction Level
Match the message weight to what's being requested. Executives reply to low-friction asks.
- Informational interview: Ask for 15–20 minutes, offer to work around their schedule, name a specific topic — never "pick your brain"
- Mentoring: Never open with "will you mentor me" — open with a single question or a request for one conversation; mentorship forms over time
- Networking intro: Ask for one introduction to one named person, or advice on who to talk to — not open-ended access
- Advice on a decision: Frame a specific, answerable question that respects their expertise
Rule: the first message asks for the smallest possible yes.
Step 2: Build the Connection Hook
The opening line proves this is not a mass message. Rank the available connection points by strength:
- Mutual contact (strongest): "[Name] suggested I reach out"
- Shared institution or affiliation: alma mater, prior employer, program cohort
- Their specific work: a talk, article, product launch, or interview — cite the actual thing
- A company or career moment: a recent milestone, transition, or public decision
Write the hook so it could only have been written to this one person. Reject any opener that would work if you swapped in a different name.
Step 3: Generate 5 Message Variations
Produce five distinct messages so the user can choose the fit:
Message 1 — The Direct Specific Ask. Hook → one-sentence context → single clear ask → easy close. Under 100 words. Best for busy executives.
Message 2 — The Admiration-Led. Opens with genuine, specific respect for their work → connects it to the user's path → soft ask. Best when the connection is their public work.
Message 3 — The Warm-Intro Forward. Written assuming a mutual contact is CC'd or referenced. Leads with the mutual name, thanks the connector, states the ask. Best for referred outreach.
Message 4 — The Peer-Framed Question. Positions the user as a serious, thoughtful person with a genuine question — not a supplicant. Leads with the specific question, then the ask to discuss it. Best for later-career professionals.
Message 5 — The Value-Aware. Acknowledges the executive's time explicitly, offers flexibility, and names what makes this worth their 15 minutes. Best for very senior targets (C-suite, founders).
Each message must include:
- A subject line (for email) or opening line (for LinkedIn)
- The full message body
- A one-line note on which situation it fits best
Step 4: Write the Follow-Up
For each channel, provide one follow-up message to send 5–7 business days after no reply:
- Reference the original message briefly without guilt-tripping
- Add one new small piece of value or context
- Restate the ask even more simply
- Keep under 60 words
Step 5: Flag the Traps
Before delivering, note any of these that appear and correct them:
- "Pick your brain" / "grab coffee" with no purpose
- Multi-part asks in a first message
- Flattery that isn't specific ("I've always admired you")
- Long autobiography before the ask
- Asking for a job directly in a cold message
Output Format
- Structure: 5 numbered message variations, each with subject/opening line, body, and fit-note → follow-up messages by channel → trap-check notes
- Length: 700–1,000 words
- Format: Structured — each message clearly labeled and copy-paste ready
- Sections: Ask & channel summary → 5 message variations → Follow-up messages → Trap check
- Tone: Professional, warm, and confident without being deferential or overfamiliar — reads like a sharp peer, not a fan or a supplicant
Quality Checklist
Before delivering output, verify:
- [ ] All 5 message variations are present and distinct in approach
- [ ] Each message contains exactly one primary ask — not stacked requests
- [ ] Every opener references a specific, true connection point — none are swappable to another recipient
- [ ] No message exceeds ~100 words for the first contact (follow-ups under 60)
- [ ] Each message has a subject or opening line and a fit-note
- [ ] No banned phrases appear ("pick your brain," generic flattery, direct job ask)
Notes
- The single biggest reply-rate driver is a specific hook — a message that proves you researched the person outperforms a polished but generic one every time.
- Discourage asking for mentorship outright in a first message; frame it as one conversation and let the relationship earn the label.
- For C-suite and founder targets, brevity is respect — Message 1 and Message 5 tend to perform best.
- Remind the user to send during business hours in the recipient's time zone and to personalize the connection line even further if they learn something new before sending.
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