dallasandrews1 When This Skill Applies
- Run AFTER the Outreach First Draft Engine has produced the draft. The First Draft Engine is the pre-production thinking framework; this skill is the post-production quality gate. Do not use this skill as the starting point for writing outreach copy. If the First Draft Engine has not been loaded yet, load it first.
- Run on every piece of outreach copy before sending to a prospect
- Run after drafting emails, LinkedIn messages, voice scripts, or call scripts
- Run before sending any cold outreach or multi-prospect sequence
Background
The Copy Sharpener enforces excellence at the word level. Enterprise executives receive hundreds of emails per week. Flabby copy gets deleted. Every word must earn its place. The skill applies 9 disciplined rules that strip away filler, enforce the Value Stack framework, front-load value, and ensure tone matches persona. It then flags every change and explains why.
Critical context: This skill is a VERIFICATION layer, not a CONSTRUCTION tool. The First Draft Engine produces the draft by thinking from the prospect's chair, locking one idea, writing the whole message as a flowing thought, and passing the Prospect Test. THIS skill then checks that draft against the 9 rules and checklist. If the Sharpener flags a rule violation but the message reads naturally and passes the Prospect Test, the message wins. If the Sharpener flags something that genuinely breaks the spell (forbidden word, wrong format), fix it without disrupting the flow. The fluidity of the whole message is more important than any single rule passing.
CTA Philosophy (North Star)
Every piece of outreach copy exists to accomplish one thing: make the prospect reflect on THEIR problem and want to solve it badly enough to talk to someone about it. These principles override every other CTA rule in this skill when they conflict.
- Prospect is the hero. Every email makes THEM the central figure, not you, not your company, not the solution.
- Feel, not tell. Make them FEEL the problem through the words, not be TOLD about it. Never declare their responsibilities to them. Instead, describe the situation so vividly they self-select into it.
- Self-selection pattern. Describe the situation so the prospect sees themselves in it. WRONG: "You own the gap between infrastructure and experience." RIGHT: "That gap between infrastructure and experience is where digital leaders are spending their time right now."
- Meeting is their idea. The email creates the tension; the prospect resolves it by wanting to talk. You don't ask for the meeting. You make the meeting the obvious next step.
- CTA connects the dots. If the CTA doesn't make the meeting feel like it solves THEIR problem, the email failed, no matter how good the body is.
Workflow Steps
Capture Draft Copy
- Paste the exact draft email, LinkedIn message, voice script, or call script
- Note the intended recipient (CFO, VP Digital, CTO, etc.)
- Note the communication channel (cold email, LinkedIn InMail, voice note, etc.)
- Note the goal (book call, send business case, technical validation, etc.)
Apply Rule 1: So What Chain
- Read each sentence. Ask: "So what? Does the reader care?"
- Delete sentences that don't answer "why should I care?"
- Examples of low-So-What sentences:
- "We're excited to connect with you." (So what? They've heard this 100 times)
- "Our solution is innovative." (So what? Everyone claims innovation)
- "We help companies improve engagement." (So what? Vague, no specific pain)
- Rewrite to be specific and recipient-centric.
Apply Rule 2: Value Stack Framework Check
- Every email/message should follow: Observation -> Insight -> Value -> Next Step
- Observation: What did you see? Specific to them. (e.g., "Your NPS dropped 8 points in Q3")
- Insight: What does it mean? (e.g., "Onboarding friction is the top driver in the exit surveys")
- Value: Why does it matter to them? (e.g., "That's a $2.4M retention gap at your current churn rate")
- Next Step: What's the ask? (e.g., "Worth 15 mins to talk through what we found?")
- If any element is missing or weak, strengthen it
- If the message has extra sentences that don't map to the Value Stack, delete them
Apply Rule 3: Length and Front-Loading Limits
- Cold Email 1: 80-120 words maximum
- Cold Email 2+: 120-150 words maximum
- LinkedIn InMail: 2-3 sentences maximum (50-80 words)
- LinkedIn DM: 3-5 sentences maximum (50-100 words)
- Voice Note: Under 45 seconds (~100-125 words). Every voice note MUST also include a TL;DL (too long; didn't listen) written summary (2-3 sentences).
- Voicemail: Under 25 seconds (~50-60 words)
- Cold Call Opening: Under 45 seconds (~100 words). Structure: Opening (8-10 sec), Hook (15-20 sec), Bridge (10-15 sec), CTA (5-10 sec)
- Front-load value: The first 1-2 sentences must contain the most compelling insight. If the reader stops after the first sentence, they should understand why you're reaching out.
- Count words. Cut ruthlessly. Every word must earn its place.
Apply Rule 4: Brand-Light Execution (Days 1-5)
- Days 1-5 of outreach: Do NOT mention your company by name anywhere. Not in subject lines, email bodies, LinkedIn notes, voice scripts, or signatures.
- Sign-off Days 1-5: First name only (warmer and more personal)
- Sign-off Day 6+: Full name (representing the company once it's named)
- Never sign as "Name, Company" or "Name | Company" in any email.
- Frame solution as category, not product: "member engagement platform," "activation solution," "revenue intelligence system"
- Your company can appear starting Day 6, but sparingly and only when it adds credibility
Apply Rule 5: Forcing Function Specificity
- The opening must reference the specific forcing function or pain point
- VAGUE: "I saw you're in the fintech space."
- SPECIFIC: "Your churn rate jumped 2 points YoY, and support cost per ticket is up 15%."
- VAGUE: "You probably care about customer experience."
- SPECIFIC: "Your app is at 3.2 stars on iOS. Onboarding completion is the top complaint."
- If the draft doesn't reference a specific, data-backed forcing function, rewrite it
Apply Rule 6: CTA Construction and Escalation
- Connector sentence (REQUIRED before every CTA question): Add one sentence just before the CTA that connects the prospect's specific role/pain to why THIS meeting matters to THEM specifically.
- Every CTA must specify WHAT the meeting is about. WRONG: "Worth 15 minutes?" RIGHT: "Worth 15 minutes to walk through what the winning retention playbooks actually looked like?"
- One question, one ask. Never stack two questions back-to-back.
- Never repeat the "how" in the CTA if it's already in the paragraph above.
- Format-specific CTA rules:
- Emails (longer format): Specify what the 15 minutes is for.
- LinkedIn DMs (shorter format): "Worth a quick conversation?" is enough. Don't make a DM feel like an email.
- Seniority-calibrated timing:
- Directors and mid-level: "early next week" or "this week" is fine
- VPs, SVPs, C-suite: "in the next couple weeks." They don't open calendars in 5 days for cold outreach.
- Escalation schedule:
- Email 1: Soft CTA ("Think it's worth finding 15 min to [specific value]?")
- Email 2: Slightly stronger ("Worth a quick call to walk through [what you found]?")
- Email 3: Direct ("Let's set up 15 mins. I've got [specific deliverable] ready.")
- Email 4: Formal ("Available [timeframe]?")
- Email 5: Final ("This is worth your time. I'm here whenever the timing lines up.")
- Week 2: Move to phone/voice as channel
- Day 1 Email Three-Beat Close (REQUIRED):
- Short proof point sentence about a peer/comparable org
- Standalone "Might be helpful/useful/valuable to walk you through..." sentence
- Blank line, then "Worth 15 min in the next few weeks?" as its own line
- Blank line, then first name sign-off
- NEVER end on a statement. Every CTA must be a question.
- NEVER use commanding CTAs. "Let me send over a couple times" tells the prospect what to do. Ask, don't command.
- NEVER use weak/passive CTAs. "I can walk through what I found" or "if at all" hedge and undercut confidence.
Apply Rule 7: Persona and Tone Matching
- CFO persona: Metrics-driven, concise, ROI-focused. Tone: executive summary, numbers, no jargon.
- VP Operations persona: Process-driven, efficiency-focused. Tone: operational, specific, FTE impact.
- VP Digital / VP Product persona: Engagement-driven, innovation-focused. Tone: consultative, partnership, NPS/metrics.
- CTO persona: Technical-focused, risk-averse. Tone: technical specification, architecture, third-party validation.
- CMO persona: Brand/positioning-focused. Tone: strategy, differentiation, competitive.
- Check every sentence: Does it match this persona's values and tone?
Apply Rule 8: Linguistic Guardrails
- NO FORBIDDEN WORDS: leverage, synergy, cutting-edge, best-in-class, empower, seamless, robust, transform, transformation, catalyst, paradigm, innovative, comprehensive
- NO vague language: "exciting," "great," "amazing," "powerful"
- NO qualifying phrases: "I think," "in my opinion," "hopefully," "I believe"
- NO defensive language: "I know you're busy," "I'm sure you get a lot of emails"
- NO cliches: "circle back," "touch base," "reach out," "at the end of the day"
- NO em dashes in prospect-facing copy. They are an AI writing giveaway. Replace with periods, semicolons, commas, or colons.
- NO engagement tracking references in prospect-facing copy. Never mention email opens, link clicks, or engagement signals.
- NO robotic or fragmented copy. Emails should read like a real person wrote them in one sitting. Add connective tissue between ideas. Vary sentence length. Merge consecutive short declarative sentences in body paragraphs.
- NO formulaic transitions ("Result:", "Key takeaway:")
- Subject lines must be short, lowercase, conversational. No title case.
Apply Rule 9: Send-Ready Test (20-Point Checklist)
- Does it start with specific observation (not generic greeting)?
- Is the forcing function data-backed (not assumed)?
- Does it answer "so what" for the reader?
- Is it Value Stack complete (Observation -> Insight -> Value -> Next Step)?
- Is it under word count limit for this channel?
- Does first sentence hook the reader?
- Is CTA appropriate to email position in sequence?
- Does CTA have a connector sentence linking their role/pain to why the meeting matters?
- Does CTA specify WHAT the meeting is about?
- Is there only ONE question in the CTA?
- Is the prospect the hero (never told what their job is)?
- Does it make them FEEL the problem rather than being TOLD about it?
- Does it match persona tone?
- Does it avoid all FORBIDDEN WORDS?
- Does it avoid vague language?
- Is company name absent from Days 1-5 copy (including signatures)?
- Is sign-off first name only (Days 1-5) or full name (Day 6+)?
- Are there zero em dashes in prospect-facing copy?
- Does it sound like a peer, not a salesperson?
- Would you send this from your own email?
- Do body paragraphs flow naturally without staccato chains?
- Does Day 1 email CTA follow three-beat close?
Create Changes Log For every change made, document: Original text, Sharpened text, Rule applied, Rationale.
Return Sharpened Copy + Changelog
- Output: Sharpened version of copy (ready to send)
- Output: Side-by-side comparison showing original vs. sharpened
- Output: Changelog with rationale for every edit
Cold Call, Voice Note, Voicemail, and Video Standards
Cold Call Script Standards
- Maximum 45 seconds spoken (~100 words). Prospect decides in 8 seconds whether to keep listening.
- Structure: Opening (8-10 sec), Hook (15-20 sec), Bridge (10-15 sec), CTA (5-10 sec).
- Opening MUST NOT: Start with "I know you're busy." Use company name first. Ask "Do you have a minute?"
- Hook MUST: Reference something specific to this account.
- CTA MUST be assumptive: "I think it'd be worth 10 minutes" not "Would you be interested?"
- Objection handlers must be included for: "Who is this?", "Not a good time", "Send me an email", "We're already working on this."
Voice Note Standards
- Under 45 seconds (~100-125 words).
- Structure: Quick intro (first and last name, no title, no company), one specific credible reference, one insight showing pattern recognition, soft next step.
- Tone: Like leaving a message for a colleague you respect.
- ALWAYS include: One specific, verifiable reference to something about their business.
- TL;DL: Every voice note MUST be accompanied by a 2-3 sentence written summary.
Voicemail Standards
- Under 25 seconds (~50-60 words).
- Structure: Name, one sentence of context, callback reason. That's it.
- No pitch. No value prop. No company description.
Video Script Standards
- Under 3 minutes. Structure: Screen share of their actual data (30 sec), walk through 2-3 friction points (60-90 sec), reference one peer outcome (30 sec), soft CTA (15 sec).
- NEVER: Turn it into a product demo. Show THEIR data and THEIR problem.
LinkedIn Touch Logic
- Connection pending/not accepted: Send as LinkedIn InMail. Include voice note DM version as backup.
- Connection JUST accepted (within 24-48 hrs): Send a SHORT TEXT DM first. Save voice note for escalation.
- Long-standing 1st degree connection: Send as LinkedIn VOICE NOTE DM.
- All voice note DMs: Include a TL;DL text message immediately after.
- LinkedIn connection requests: Always send blank. No personalized message.
Multi-Persona Differentiation
When generating scripts for multiple personas within the same account, each script MUST:
- Reference a DIFFERENT forcing function or pain point
- Use vocabulary appropriate to that persona
- Have a DIFFERENT opening
- Have a DIFFERENT CTA framing
CTA Standards (All Channels)
- Days 1-2: Soft. "Given [connector], think it's worth finding 15 min to walk through [specific value]?"
- Days 3-5: Moderate. "Worth a quick call to walk through [what you found]?"
- Days 6-8: Direct. "I've got [specific deliverable] mapped out. Worth 15 minutes?"
- Days 9-10: Confident close. "This is worth your time. I'm here whenever the timing lines up."
- NEVER use: "Compare notes?", "Pick your brain?", "Touch base?", "Circle back?", "Does that make sense?", "Would you be interested?", "if at all"
- ALWAYS: Soft early, direct late. Desperate never. One question only.
Output
Format:
# Copy Sharpener Session
Date: [Date]
Channel: [Email / LinkedIn InMail / Voice Note / Call Script]
Recipient: [Name, Title, Account]
Sequence Position: [Email 1 / Email 2 / etc.]
Goal: [Book call / Send business case / Technical validation / etc.]
## Original Draft
[Paste original copy exactly]
## Send-Ready Test Results
[Checklist with PASS/FAIL per item]
**Test Result**: [PASS / FAIL]
---
## Sharpened Copy (Ready to Send)
[Final, polished copy]
---
## Changes Log
[Per-change breakdown with original, sharpened, rule, rationale]
---
## Word Count Analysis
- Original: [X] words
- Sharpened: [Y] words
- Limit: [Z] words
- Status: [PASS / OVER]
---
## Tone Check
- Persona: [role]
- Tone Required: [description]
- Tone Delivered: [assessment]
- Match: [MATCH / MISMATCH]
---
## Value Stack Verification
- Observation: [what's in the copy]
- Insight: [what's in the copy]
- Value: [what's in the copy]
- Next Step: [CTA]
- Complete: [YES / NO]
---
## Final Recommendation
[1-2 sentence assessment of copy readiness]
About
Built by Dallas Andrews. Part of a 30+ skill AI-powered operating system adopted by five departments without a mandate.