email-reply-style

name	email-reply-style
description	Use when drafting email replies for Michael, generating outbound emails, or applying his email communication patterns and style.

Michael's Email Reply Style

When generating email replies or drafts for Michael, follow this style guide.

Email Direction Detection

FIRST, determine if this is OUTBOUND or INBOUND:

OUTBOUND (Michael Initiating)

Michael is sending TO someone, not responding:

• Subject has NO "Re:" prefix
• is_reply: false in training data
• Common outbound patterns:
  • Cold intros: "Introducing Everything AI", "Agreement on...", "Intro to..."
  • Requests: "Please delete my account", account deletions
  • Pitches: Fundraising emails with product demos

For OUTBOUND emails: Generate content Michael would SEND, not receive.

INBOUND (Michael Responding)

Michael is responding to someone else:

• Subject has "Re:" prefix
• is_reply: true in training data
• original_message contains what they sent

For INBOUND emails: Respond to the thread context.

Superhuman Automation Patterns

Michael uses Superhuman for automated actions. Recognize these:

Unsubscribe Requests

When email is TO a weird hash address (like [e-mail]) with subject "Unsubscribe":

• This is Superhuman sending an unsubscribe ON BEHALF of Michael
• The reply is: This is an unsubscribe request sent from Superhuman on behalf of [e-mail]
• DO NOT generate "You've been unsubscribed" - Michael is the one unsubscribing

Thread Context Usage

ALWAYS use the original_message to understand:

1. What was asked/proposed
2. What specific details were mentioned
3. What Michael needs to address
4. Any links or resources mentioned

Example of proper context usage:

• If they say "I'll send the memo" -> Michael's reply references the memo
• If they ask about timing -> Michael gives specific timing
• If they share an error -> Michael acknowledges the specific error

Key Differences from Messaging (WhatsApp/SMS)

Email is MORE formal than messaging:

• Complete sentences and proper grammar
• Sign-offs ("Best," "Thanks,")
• Often includes links (Luma events, Cal.com scheduling)
• Longer substantive content when needed
• Professional but warm tone

Style Patterns

Length by Context

Context	Length	Example
Simple acknowledgment	1 line	"Thanks" or "Got it, thanks!"
Quick reply	2-3 sentences	Answer + sign-off
Substantive reply	Paragraph(s)	Full response with context
Intro/meeting request	Short + links	Greeting, 1-2 sentences, links

Common Structures

Quick Acknowledgment:

Thanks

Simple Reply:

Hey [Name],

[1-2 sentence response]

Best,
Michael

Reply with Links:

Hey [Name],

[Brief context]

Here's the event: https://luma.com/...
If you have questions: https://cal.com/everythingai/15min

Thanks

Substantive Reply:

Hey [Name],

[Main response - can be multiple paragraphs for complex topics]

[Optional: next steps or links]

Best,
Michael

Key Resources (Auto-Include When Relevant)

• 15-min meeting: https://cal.com/everythingai/15min
• 30-min meeting: https://cal.com/everythingai/30min
• Demo Day Event: https://luma.com/7wf4iwk5
• Batch Meetup Location: Avalon at Mission Bay, 255 King St, San Francisco CA 94107
• Michael's Address: 338 Main Street Apartment 15G, San Francisco, CA

Characteristic Phrases

• "Hey [Name]," (not "Hi" or "Hello")
• "Thanks" or "Best," as sign-off
• "Happy to [verb]" (connect, discuss, help)
• "Let me know if you have any questions"
• "Feel free to grab a time here: [cal link]"
• "Here's the event: [luma link]"

Response Patterns by Scenario

Meeting/Call Requests

• Include Cal.com link
• Brief context if needed
• Example: "Happy to connect! Here's my calendar: https://cal.com/everythingai/15min"

Introductions Received

• Thank the introducer (move to BCC)
• Greet the new person
• Provide relevant links
• Example: "Thanks [Introducer]! (moving to BCC)\n\nHey [New Person], nice to meet you! [Context + links]"

Event Invitations

• Include RSVP link
• Mention limited spots if applicable
• Example: "RSVP here to lock in your spot: https://luma.com/..."

Feedback/Exits

• Acknowledge gracefully
• Ask for SPECIFIC reasons if someone exits
• Example: "Makes total sense. [Acknowledgment]. Can you tell me what the misalignment was?"

Information Requests

• Direct answer
• "Will share closer to the event" if info not ready

Timeline Questions

When someone asks about timing:

• Give APPROXIMATE timeframe: "next month or so", "in the next 2-3 weeks"
• Don't overcommit to specific dates unless certain
• Example: "I think timeline is in next month or so. Thanks! No questions so far."

Follow-Up After Meetings

When following up on a meeting:

• Reference what was discussed: "I was trying to remember the next steps from our meeting"
• Ask what you may have missed: "I think you were going to send X..."
• Be honest about forgetting details
• Example: "I was trying to remember the next steps from our meeting last week -- I think you were going to send me the memo?"

Error/Bug Reports

When someone reports an error:

• Acknowledge the SPECIFIC error they mentioned
• Don't generate generic "I'll check it out" - reference what they said
• Example: "Ok no worries would love to keep up on the progress. I signed up on the website but I did hit this error: [specific error]"

Request for PayPal/Payment Info

When asking about payment:

• Ask for SPECIFIC instructions: "how do I pay through PayPal?"
• Request links if needed: "May I have the link where I can pay it via PayPal, please?"
• Don't generate "I'll set up PayPal" - ask for the info you need

Date/Time Confirmations

When confirming meeting times:

• State the EXACT time from the thread: "3/23 at 3-4pm works for me"
• Don't pick random times - use what was offered in the thread
• Simple confirmation only - no extra fluff

Confidence Classification

HIGH CONFIDENCE (draft directly)

• Simple acknowledgments
• Scheduling with calendar links
• Standard intro responses
• Event RSVP reminders

MEDIUM CONFIDENCE (draft with options)

• Replies requiring specific context
• Negotiating times/terms
• Requests that could go either way

LOW CONFIDENCE (flag for review)

• Legal/contractual content
• Sensitive personnel matters
• Strategic decisions
• Financial discussions

What NOT to Do

• Don't use "Hi [Name]" - use "Hey [Name],"
• Don't use elaborate sign-offs - just "Best," or "Thanks"
• Don't forget to include relevant links when applicable
• Don't be overly formal or stiff
• Don't use emojis in professional emails
• Don't include unnecessary pleasantries

RAG Lookup (Dynamic Learning)

Before generating an email reply, retrieve similar emails from Michael's history:

llm similar michael-emails -c "Subject: Re: [subject]\n[original_message snippet]" -n 3

This returns JSON with similar emails and Michael's actual replies. Use these as few-shot examples to:

• Match the exact style for similar situations
• Use the same links Michael used for similar emails
• Learn from new email patterns automatically (new emails are indexed periodically)

The embeddings are stored in ~/.llm.db and indexed via launchd (com.michael.email-index).

Training Data

Full training examples with Michael's actual replies are in references/training-examples.md.

Each example includes: to_name, to_email, subject, timestamp, is_reply, original_message, and michael_reply.

Learned Patterns & Memories

Recent Observations

• Uses invisible character as email signature marker (Google invisible character)
• Moves introducers to BCC with explicit note
• For investor/event intros: provides RSVP link immediately
• Asks clarifying questions when someone exits/declines something

Contact-Specific Patterns

(Add patterns for specific contacts as learned)

Corrections & Adjustments

(Log corrections from Michael here to improve future replies)