Concise Messaging

Condense messages to 5 sentences or less using the High-Five Habit framework. Most messages can and should be this concise.

Core Principles

The High-Five Habit

Primary Constraint: Most messages should be 5 sentences or less.

Supporting Principles

• Communication Method: If condensation seems forced or loses critical nuance, suggest phone/meeting instead
• Reflection Built-In: By requesting AI assistance, you have already implemented the pause principle
• Distribution Strategy: Recipient limits and timing remain your strategic choices
• Urgency Assessment: Response expectations stay under your control

Communication Philosophy

• Constraints force clarity: Brevity demands precision
• Clarity is kindness: Respect others' time through conciseness
• Every unnecessary word is time theft: Each word should earn its place
• Mirror professional tone: Match the recipient's communication style while improving clarity

Message Structure Templates

Standard Business Email

1. Context/Purpose: Why you are writing
2. Key Information: Main point or request
3. Action Item: What you need from them
4. Timeline: When you need it
5. Next Step: Clear call to action

Meeting Request

1. Context/Purpose of meeting
2. Specific topic or agenda focus
3. Suggested time options
4. Expected duration
5. Clear call to action for confirmation

Project Update

1. Current status summary
2. Key accomplishment or milestone
3. Main blocker or challenge (if any)
4. Next steps planned
5. Timeline or deadline

Introduction/Outreach

1. Who you are and context
2. Why you are reaching out
3. Specific request or offer
4. Mutual benefit or value proposition
5. Clear next step

Platform-Specific Guidelines

Email

• Start directly with purpose (skip "I hope this finds you well")
• Use clear subject lines that indicate action needed
• End with specific next steps
• Maintain professional tone while being concise

Slack/Teams

• 5 sentences typically = 1-2 messages
• If typing a third message, suggest a huddle instead
• Use threads appropriately
• Avoid paragraph-long messages

Text/WhatsApp

• If the message has paragraphs, it should be an email
• Keep to essential information only
• Use for quick confirmations and updates

Social Media (LinkedIn, etc.)

• Make your point without unnecessary storytelling
• Professional but authentic tone

Condensation Process

Step 1: Identify Core Message

• What is the single most important point?
• What action do you need from the recipient?
• What information is absolutely essential?

Step 2: Eliminate Fluff

• Remove filler phrases ("I hope," "just wanted to," "I think maybe")
• Cut redundant explanations
• Eliminate unnecessary context
• Remove corporate buzzwords

Step 3: Structure for Clarity

• Lead with the most important information
• Group related ideas into single sentences
• Use active voice
• Be specific rather than vague

Step 4: Maintain Voice

• Professional but approachable
• Direct without being rude
• Confident and clear
• Appropriate level of warmth for the relationship

Exception Framework

When to Break the 5-Sentence Rule

• Legal or compliance communications
• Emotional support situations
• First impressions that merit extra investment
• Complex technical documentation (but suggest proper format)
• Creative or personal messages where brevity might seem cold

Escalation Signals

• Condensation requires multiple rounds of back-and-forth
• Topic involves complex emotions or sensitive issues
• Technical details require extensive explanation
• Stakeholder alignment needs discussion

Quality Checks

Before Finalizing

• Does this convey the essential information?
• Is the tone appropriate for the relationship and context?
• Would I understand the next steps if I received this?
• Does this reflect a professional voice?
• Is there any ambiguity that could cause confusion?

Red Flags for Further Condensation

• Multiple topics in one message
• Backstory that does not serve the main point
• Hedging language ("I think," "maybe," "perhaps")
• Repetitive information
• Unnecessary apologies or explanations

Customization

Apply voice and style preferences from your CLAUDE.md if present. Otherwise, customize the defaults below to produce ready-to-use output without placeholders.

Include in your configuration:

• Your specific communication style preferences
• Your tone characteristics (directness, warmth, formality)
• Common scenarios you encounter
• Words and phrases you prefer or avoid
• Relationship context for frequent recipients

The framework provides structure. Your voice profile makes the output authentically yours.