SimonTheSalesBooster Skill: LinkedIn Outreach Writer
What This Skill Does
Writes personalized, non-salesy LinkedIn connection requests, first messages, follow-ups, and InMails that get replies. Uses prospect research and trigger events to craft outreach that feels human, relevant, and worth responding to.
When to Use
- You need to write a connection request for a specific prospect
- You have a new connection you want to move toward a conversation
- Your current LinkedIn messages aren't getting replies
- You need to scale personalized outreach without sounding templated
Inputs Required
Before running this skill, ask the user for:
- Prospect name, title, and company
- One personalization detail — a trigger event, something they posted, a mutual connection, or company news
- What you sell — one sentence on the core problem you solve
- Goal of this outreach — connection, conversation, or meeting?
- Tone preference — casual and direct, warm and conversational, or executive-level?
Default Approach: Jay Abraham Preeminence
All outreach defaults to the Preeminence framework. Do not wait to be asked.
Jay Abraham's Preeminence principle means positioning yourself as the most trusted advisor — someone who genuinely cares about the prospect's success, not just making a sale. Applied to LinkedIn:
- Lead with their work — reference something specific they've created, written, built, or said
- Peer-to-peer tone — no hierarchy, no vendor language, no "I wanted to reach out"
- No pitch, no ask — pure connection first, serve before asking for anything
- Mirror their language — use words and concepts from their own brand/content
- Short and direct — respect their time, get to the point
The test: Would this message feel valuable even if they never bought anything? If yes — send it. If no — rewrite it.
What to avoid:
- ❌ "I help companies like yours..." (vendor framing)
- ❌ "I'd love to learn more about your work..." (hollow)
- ❌ "Would you be open to a quick call?" (too fast)
- ❌ Generic compliments with no specifics ("Great content!")
What works:
- ✅ Reference a specific book, post, framework, or result they produced
- ✅ Show how their thinking shaped yours or your client work
- ✅ Position as a peer — "your approach and mine overlap"
- ✅ End with connection intent, not a CTA
Step-by-Step Instructions
Step 1 — Select the Outreach Type
Determine which message type is needed:
| Situation | Message Type |
|---|---|
| Not yet connected | Connection Request (300 chars max) |
| Just connected (day 0–3) | First Message (value or curiosity) |
| Connected, no reply after 5 days | Follow-up 1 (different angle) |
| Connected, no reply after 10 days | Follow-up 2 (soft close or break-up) |
| Paying for InMail | InMail (longer, more context) |
Step 2 — Write the Connection Request
Rules:
- Max 300 characters
- Reference ONE specific detail from their actual work (book, post, framework, methodology)
- No pitch, no "I'd like to add you to my network"
- Lead with what THEY created — not what Simon does
- Peer-to-peer tone throughout
Preeminence Formula: [Their specific work/idea + how it impacted you or your clients] + [Peer connection intent] + [No ask]
Templates by trigger type:
Trigger: They wrote a book or framework
[Name] — [specific book/framework] reshaped how I [specific application with clients]. Your [methodology name] and my [adjacent approach] are closely aligned. Would love to connect.
Trigger: They posted something
[Name] — your point on [specific topic from post] is exactly the shift [their audience] needs. I work with [similar space] and see this play out constantly. Would love to connect with someone thinking this way.
Trigger: Company they built
[Name] — what you've built with [Company] is exactly what [their market] needed. I work with [adjacent space] and your approach and mine overlap in interesting ways. Would love to connect.
Trigger: Mutual connection
[Name] — [Mutual Name] suggested I reach out. We both work in [space] and your thinking on [specific topic] resonates with what I see in my client work. Would love to connect.
Step 3 — Write the First Message (Post-Connection)
Send 24–48 hours after they accept. Never pitch. Add value or open curiosity.
Formula: [Warm opener] + [Value or insight] + [Soft question or offer]
Templates:
Value Drop:
Hey [Name], glad to be connected! I've been working on [relevant topic] a lot lately and put together [resource/insight]. Given what you're building at [Company], thought it might be useful. Happy to share — want me to drop it here?
Curiosity Opener:
Hey [Name], something I've been wondering — how are you thinking about [relevant challenge] right now at [Company]? I've been talking to a lot of [title] and seeing some interesting patterns. Curious if it maps to your experience.
Insight Share:
Hey [Name], one thing I keep seeing with [title] at companies like [Company]: [specific insight or pattern]. Does that resonate with what you're seeing, or is your situation different?
Step 4 — Write the Follow-Up Sequence
If no reply in 5–7 days:
Follow-up 1 — New Angle:
Hey [Name], wanted to follow up — not sure if my last message got buried. [New angle or new piece of value]. Wondering if [question that invites a reply].
Follow-up 2 — Soft Close (Day 10–12):
Hey [Name], I'll keep this short — I don't want to keep pinging you if the timing isn't right. If [problem you solve] isn't a priority right now, totally understand. But if it is, happy to jump on a quick call. Either way, no worries — I'll let you be.
Step 5 — Write the Meeting Ask
Once there's a back-and-forth conversation, make the ask:
Low-friction meeting ask:
[Name], based on what you've shared — this feels like it could be worth a quick conversation. Would 20 minutes make sense to explore? Not a sales pitch — just want to see if there's something real here. What's your calendar like [day] or [day]?
Calendly-style ask:
Would it be easier if I just dropped a link? Here's mine — grab whatever works: [Calendly link]
Output Format
Deliver:
- Connection Request (ready to copy-paste, under 300 chars)
- First Message (post-connection, value or curiosity)
- Follow-up 1 (if needed)
- Follow-up 2 / Soft Close (if needed)
- Meeting Ask (when ready)
All messages personalized with the details provided. Each clearly labeled and ready to send.
Pro Tips
- The first message sets the tone for the entire relationship — make it about them, not you
- If your connection request acceptance rate is below 35%, your target is wrong or your message is too salesy
- The best follow-up is a NEW insight or angle, not "just checking in" — that's a conversation killer
- Never ask for a meeting in a connection request — it's the LinkedIn equivalent of proposing on a first date
- Short messages outperform long ones 4:1 on LinkedIn — get to the point fast
- Always end messages with a question or a clear action — open loops keep conversations alive