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Optimize messages for desired outcome - fix English, kill red flags, simulate recipient

VCasecnikovs By VCasecnikovs schedule Updated 4/24/2026

name: comms description: Optimize messages for desired outcome - fix English, kill red flags, simulate recipient user_invocable: true auto_trigger: true trigger_description: Load when the user pastes a message to review, asks to fix/optimize a message, or when drafting outbound comms in heartbeat

Comms - Communication Optimizer

Optimize any message the user sends so the recipient does what they need.

Not a grammar checker. This is a 4-layer system that goes from fixing English all the way to simulating what the recipient will think, feel, and do.

Related: english-coach skill has the passive reference (slang, phrases, Russian mistakes).


The 5 Layers

Run top to bottom. Each layer builds on the previous.

Layer 0: HUMAN

Does this look like a person typed it?

This layer runs LAST as a final pass. It catches the #1 failure mode: output that's technically perfect but obviously AI-written. A message the user couldn't have typed themselves destroys trust.

Medium-aware formatting:

Medium Formatting rules
TG / Signal / DM NO bold headers. NO bullet points. NO markdown. Paragraphs OK but keep them ragged. Dense blocks > structured sections. Occasional sentence fragment OK
Email (casual) Light formatting. One bold max. Short paragraphs
Email (formal) Clean structure OK. Headers OK. Still no over-formatting
Proposal / doc Full formatting allowed

AI smell test - kill these patterns:

  • Special characters nobody types: ° (em dash) - replace with deg, ->, -, -, ~. Real people on phones don't have these
  • Perfect parallelism: if every paragraph starts the same way (e.g. bold keyword + colon), break the pattern. Real writing is asymmetric
  • Zero typos from a non-native speaker: if the user's English level wouldn't produce this level of polish, it's suspicious. Don't ADD typos, but don't fix every minor roughness either. A slightly awkward phrase that sounds like the user > a perfect phrase that sounds like Claude
  • Compliment sandwiching: "great work! ... but have you considered... enjoy the trip!" - the praise-suggestion-praise structure is an AI tell. If the user would just say it, just say it
  • Over-praising the recipient: "strong result, congrats!" on every message = performative. Real peers acknowledge good work briefly or not at all. One "nice" or "cool" is more believable than "impressive, congrats!"
  • Too many specific numbers in compliments: citing their exact RMSE back to them in the opening line = showing off that you read it. One reference is smart. Three is AI
  • Hedging language clusters: "could potentially", "it might be worth considering", "perhaps exploring" - real founders say "what about X?" or just state it

The test: Would the user's peer think "did they use ChatGPT for this?" If yes, rough it up. The goal is a message that's clearly the user but with better English - not a message that's clearly AI but with their name on it.

Rule of thumb: Fix errors that make the user look bad (grammar mistakes, wrong words). Keep roughness that makes the user look real (dense paragraphs, missing transitions, casual structure).

Layer 1: NATURAL

Does it sound like a native speaker wrote it?

  • Fix grammar, articles, prepositions
  • Match register: formal (emails, proposals, enterprise) vs casual (DMs, Twitter, founder chats)
  • Kill known Russian patterns (CLAUDE.md Top 5 errors):
    • "we are having" → "we have"
    • "I do believe" → delete or "I think"
    • "right now" overuse → cut it
    • "I were" → "I was"
    • "would love to" x5 → rotate alternatives
  • Reference: english-coach skill for vocabulary and phrase library

Layer 2: CLEAR

Am I saying what I mean? Would a native speaker understand instantly?

  • One idea per sentence. Max 12-15 words
  • Patch vocabulary gaps (when the user uses a sentence to describe what one word covers)
  • Cut filler: "basically", "actually", "in terms of", "the thing is that"
  • Lead with the point, not the context
  • Kill nested clauses (Russian sentence structure leaking through)
  • BUT for casual mediums (TG/DM): don't over-split. Dense paragraphs are normal in chat. A wall of text is more human than a perfectly structured outline

Layer 3: SAFE

Would anything in this message hurt the user's position?

Scan for:

  • Weakness signals - "unfortunately", "we don't have yet", "I'm not sure", unnecessary hedging, apologizing for nothing
  • Oversharing - revealing pricing to wrong audience, internal struggles, team size, technical limitations, deal details with other clients
  • Desperation - "I would be very grateful", "whenever works for you", too many exclamation marks, over-eagerness
  • Legal risk - promises of exclusivity, guarantees, IP claims without basis
  • Status drops - anything that makes the user look junior, small, or needy
  • Deal breakers - mentioning competitors by name, admitting data gaps, price anchoring too low, revealing urgency
  • Confidentiality - client names, revenue numbers, internal metrics that shouldn't be shared (check Obsidian Products access: field)

Don't just remove - reframe. Turn weaknesses into neutral or positive statements:

  • ❌ "Unfortunately we don't have video data yet" → ✅ "Video is on our roadmap for Q2"
  • ❌ "We're a small team" → ✅ "We move fast - small team, direct access to founders"
  • ❌ "I'm not sure about the pricing" → ✅ "Let me get back to you with exact numbers by Friday"

Layer 4: EFFECTIVE

What will the recipient DO after reading this?

This is the most important layer. The message exists to trigger an action.

Process:

  1. Identify recipient - from context, or ask the user
  2. Pull context - Obsidian People note, deal note, Organization note, past conversation
  3. Ask the user (if not obvious): "What do you want them to DO?" - reply, schedule call, approve, sign, intro, buy, share info
  4. Model the recipient:
    • What's their role? (decision-maker vs evaluator vs connector)
    • What do THEY want? (their incentives, pain points, KPIs)
    • What's their communication style? (fast/slow, formal/casual, detail-oriented/big-picture)
    • Where are we in the relationship? (cold → warm → hot → closing)
    • What's blocking them from doing what we want?
  5. Simulate reaction: Given this person reads this message → what do they think? Feel? Do?
  6. Compare simulated action vs desired action. If mismatch → rewrite
  7. Show simulation to the user with confidence level

Common recipient archetypes:

Type Wants What works What kills it
Enterprise buyer Risk reduction, ROI, compliance Case studies, timelines, data Hype, unproven claims
VC / investor Traction, team, market Numbers, confidence, vision Desperation, vague metrics
Technical evaluator Specs, benchmarks, integration Detail, honesty about limits Marketing speak
Founder / peer Speed, mutual value Directness, shared context Formality, long emails
Connector Easy ask, clear value Brief context, specific request Long background stories
Researcher Methodology, data quality Technical depth, reproducibility Sales language
Government / intel Capabilities, security, compliance Formal proposals, references Casual tone, overselling

How to Use

Manual: /comms

The user pastes a message and says who it's for + what they want them to do.

Output format:

📝 ORIGINAL
[Original text]

🔄 REWRITE
[Optimized version]

📊 WHAT CHANGED
L0 Human: [AI patterns killed / roughness preserved]
L1 Natural: [fixes]
L2 Clear: [simplifications]
L3 Safe: [red flags killed]
L4 Effective: [strategic changes]

🧠 RECIPIENT SIMULATION
They read this and think: [...]
They feel: [...]
They do: [...]
Match with desired outcome: [✅ high / ⚠️ medium / ❌ low]

💡 ALTERNATIVES (if match < high)
Option A: [different angle]
Option B: [different angle]

Auto-trigger: during heartbeat / message drafting

When drafting replies for the user:

  • L1-L3 run silently (natural + clear + safe)
  • L4 runs when recipient is known and goal is clear
  • Flag L3 issues explicitly - never let a red flag through

Practice mode

When the user writes to practice:

  • Run all 4 layers
  • Show original → rewrite with explanations per layer
  • Rate naturalness 1-5
  • Highlight which Top 5 patterns appeared
  • Suggest one new phrase from english-coach reference that fits the context

Key Principles

  1. Desired outcome drives everything. Grammar is layer 1. The real value is layer 4.
  2. Every message has a job. If a message doesn't move toward a goal, ask why it exists.
  3. Confidence > correctness. A slightly wrong but confident message beats a perfectly correct but weak one.
  4. Short > long. Busy people read short messages. Write less, say more.
  5. The recipient is an NPC. Model their behavior. Optimize your input to get the output you want.
  6. Context is king. A message to a cold lead vs a warm contact vs a closing deal = completely different strategies. Always pull context first.
  7. Human > perfect. A message that sounds like the user wrote it beats a message that sounds like AI wrote it. Fix errors, keep voice. The rewrite should be something the user COULD have written - not something only an AI would produce.
  8. Minimal intervention for casual. For TG/DM/Signal: fix the Top 5 errors, kill L3 red flags, leave the rest alone. Don't restructure, don't add headers, don't polish. The user's rough draft + 2-3 fixes > full AI rewrite.
Install via CLI
npx skills add https://github.com/VCasecnikovs/klava --skill comms
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