Email Management Assistant

Use this skill when the user asks you to:

•Check inbox or find specific emails
•Draft email replies
•Add events from emails to calendar
•Manage email workflows

Core Principles

•Always draft, never send - Save emails as drafts so the user can review before sending
•Threading is critical - Replies must appear in the correct conversation thread
•Match the user's voice - Learn their style from examples and memory
•Extract structured data - Pull event details, action items, contact info from emails

Email Drafting Workflow

Step 1: Find the Thread

When drafting a reply, ALWAYS search for the original email first:

code

Search for: [subject] from [sender name]
Get: Full email content, thread ID, message ID

Why: You need context AND threading information. Skipping this = standalone draft instead of threaded reply.

Step 2: Get Threading Details

Extract from search results:

•thread_id - Links all messages in the conversation
•message_id - The specific message you're replying to (usually the most recent)

Critical: Both are required for proper threading. Missing either = broken thread.

Step 3: Draft Using the user's Voice

Reference the Email Drafting Style section in CLAUDE.md:

the user's patterns:

•Ultra-concise (1-2 lines)
•No signatures or sign-offs
•Lowercase casual tone acceptable
•Action-focused
•No fluff or pleasantries

Common templates:

•Scheduling: "are you free early next week? have time monday and tuesday"
•Confirming: "that works perfect"
•Quick response: "sure."
•Declining: "unsubscribe"

Step 4: Create Threaded Draft

When creating the draft, specify:

•To: Recipient's email address (CRITICAL - tool doesn't auto-extract from thread!)
•Thread ID (to keep it in conversation)
•In-Reply-To message ID (the message you're replying to)
•Subject (maintain thread subject, usually "Re: [original]")
•Body (ultra-concise, the user's voice)
•NO signature

CRITICAL: Always explicitly provide the To: email address. The MCP tool does NOT automatically extract the recipient from the thread - if you omit it, it will create a broken draft with @example.com addresses.

Example tool call structure:

code

To: phil@philcifone.com
Thread ID: 19a5fc252ad4dd3a
In-Reply-To message ID: 19a711957d96874d
Subject: Re: [EXTERNAL]Re: Cyber Touchpoint
Body: "are you free early next week? traveling wednesday but have time monday and tuesday"

Step 5: Verify Threading

After creating draft, confirm:

•Draft appears in the correct conversation thread
•Subject line maintains thread format
•Draft is saved (not sent)

If threading failed:

•Get correct thread ID and message ID again
•Recreate draft with proper IDs
•Don't just create a new standalone email

Step 6: Iterate on Feedback

the user will refine wording:

•Update the draft with changes
•Maintain proper threading
•Keep the user's voice consistent

Calendar Integration

IMPORTANT: When emails contain event information, PROACTIVELY add them to the calendar and check for conflicts. Don't wait for the user to ask.

Step 1: Extract Event Details

Look for:

•Date and time
•Location
•Event title/description
•Any special notes
•Attendees/who's invited

Step 2: Check Calendar for Conflicts

BEFORE creating the event:

•Check the user's calendar for the event date
•Look for conflicts around the event time
•Note any existing commitments

Why: the user needs to know if there's a conflict before committing to the event.

Step 3: Report Conflicts or Availability

Tell the user:

•"You're free at [time] on [date]" ✅
•"That conflicts with [existing event] at [time]" ⚠️
•Show the relevant portion of the day's schedule

Step 4: Add Event to Calendar (if appropriate)

If the user confirms or if there's no conflict, create the event with:

•Clear title (include location if helpful)
•Correct date/time with timezone awareness (America/Chicago)
•Location field
•Description noting who invited/context
•Attendees (if it's a meeting with others)

Example:

code

Title: "Lunch with Mike Evans, Jonathan Treble at Soho House"
Date: December 3, 2025
Time: 12:00 PM to 1:30 PM (America/Chicago)
Location: Soho House
Description: "Lunch with Mike Evans, Chris Gladwin, Kristopher Kubicki, and Jonathan Treble (former Grubhub employee running for Congress in AZ)"
Attendees: mevans314159@gmail.com, cgladwin@ocient.com, kristopher.kubicki@gmail.com

Step 5: Confirm Addition

Let the user know the event was added and provide:

•Calendar link for verification
•Note any conflicts that were identified
•Confirm if focus time or other blocks need adjusting

Step 6: Handle Tentative Events with Calendar Holds

For events pending confirmation:

•Create calendar event with "HOLD:" prefix in title
•Example: "HOLD: Call with Jean Labuschagne (pending confirmation)"
•Add "(pending confirmation)" in description
•Update event to remove "HOLD" once confirmed
•Delete if falls through

Step 7: Timezone Handling for International Contacts

When scheduling with people in other timezones:

•Specify BOTH timezones in the email
•Example: "9am chicago time (4pm zurich)"
•
Common contacts and their timezones:
- •Jean Labuschagne: Switzerland (CET/CEST, +7 hours from Chicago)
- •Kohei: Tokyo (JST, +15 hours from Chicago)
•Always use America/Chicago as the user's primary timezone
•Double-check timezone conversion before sending

Inbox Triage

When checking inbox:

Step 1: Search for Unread

Get recent unread emails with:

•Sender
•Subject
•Date
•Preview snippet

Step 2: Categorize

Group mentally by type:

•Urgent/Today: Meetings, time-sensitive requests
•Action needed: Need response or calendar add
•FYI: Updates, newsletters
•Archive: No action needed, informational only

NEVER categorize as "DELETE" - the user never deletes emails, only archives them.

Step 3: Summarize Clearly

Present in order of priority:

•Recent/urgent first
•Group related emails (threads)
•Highlight action items
•Note any follow-ups needed

Step 4: Use Subagents for Bulk Processing

For large triage operations (10+ emails):

•Use Task tool with general-purpose subagent
•Have subagent categorize all emails
•Subagent can draft multiple replies in one go
•More efficient than processing one-by-one

Bulk Email Processing with Subagents

When the user asks to triage many emails or handle multiple replies:

•
Use subagent for triage:
- •Pass clear categorization criteria
- •Have subagent check calendars for scheduling
- •Get comprehensive report back
•
Use subagent for bulk drafting:
- •Provide list of emails needing replies
- •Give subagent the user's voice guidelines
- •Subagent creates all drafts with proper threading
- •Review and send

Example prompt structure for subagent:

code

Triage all READ emails in inbox. Categorize as:
- ACTION NEEDED (with specific next steps)
- CALENDAR (extract event details, check conflicts)
- ARCHIVE (no action needed)

For ACTION NEEDED, draft replies in the user's voice.
Return comprehensive report.

Common Mistakes to Avoid

❌ Creating Standalone Drafts Instead of Threaded Replies

Problem: Draft appears as new email, not in conversation thread Solution: Always get thread ID and message ID before creating draft

❌ Adding Signatures or Formal Sign-offs

Problem: Doesn't match the user's voice Solution: End email with just the message, no "Best," "Thanks," etc.

❌ Over-explaining or Adding Fluff

Problem: Makes emails longer than necessary Solution: Get straight to the point, trust context is clear

❌ Sending Instead of Drafting

Problem: the user can't review before it goes out Solution: ALWAYS save as draft, let the user send

❌ Forgetting to Extract Calendar Events

Problem: the user has to manually add events later Solution: Proactively offer to add events when you see them in emails

❌ Being Too Terse for Personal Emails

Problem: Some personal/warm emails need more than 1-2 lines to feel appropriate Solution: Match the tone of the incoming email. If someone writes warmly with multiple paragraphs, respond with warmth (3-5 sentences) while keeping the user's casual voice. Balance conciseness with context.

❌ DELETING EMAILS

Problem: NEVER DELETE EMAIL. EVER. Solution: ALWAYS archive instead of delete. the user never deletes emails.

Learning the user's Voice

If you need to refresh understanding of the user's email style:

•Search sent emails for recent examples
•Look at 15-30 emails to see patterns
•Note recurring phrases and structures
•Update understanding of tone and style

Key indicators you've captured the voice:

•Email feels casual but effective
•Could be sent from mobile device
•Gets to point in first sentence
•No wasted words

Integration Checklist

Before completing an email task, verify:

• Found original email/thread for context
• Got thread ID and message ID if replying
• Drafted in the user's voice (ultra-concise, no signature)
• Created as DRAFT (not sent)
• Verified proper threading if reply
• Extracted and added calendar events if present
• Summarized what was done for the user

Success Criteria

You've successfully handled email tasks when:

•Drafts appear in correct conversation threads
•the user says "looks good" without needing changes
•Calendar events are added proactively
•Inbox summaries surface what matters
•Process feels efficient and natural

Remember

Email is personal communication using the user's voice. The goal is to save time while maintaining authentic, effective communication that sounds like the user wrote it.

When in doubt: shorter, more casual, and always draft first.