Email Management with Office Admin

Use this skill when handling:

• Checking inbox or finding specific emails
• Drafting email replies
• Adding events from emails to calendar
• Managing email workflows
• Bulk email triage

Core Principles

1. Always draft, never send - Save emails as drafts for user review before sending
2. Threading is critical - Replies must appear in the correct conversation thread
3. Match user's voice - Reference their office-admin config for tone and style
4. Extract structured data - Pull event details, action items, contact info from emails
5. Proactive calendar integration - Auto-check conflicts and add events

User Style Configuration

Before drafting emails, load the user's style from ~/.claude/office-admin-config.json:

{
  "email": {
    "tone": "ultra-terse" | "conversational" | "professional" | "warm",
    "signature": "none" | "minimal" | "full",
    "formality": "casual" | "standard" | "formal",
    "responseLength": "minimal" | "balanced" | "detailed",
    "patterns": ["common phrases they use"],
    "customGuidelines": "Additional freeform style notes"
  }
}

If config doesn't exist, prompt user to run /setup-office-admin first.

Email Drafting Workflow

Step 1: Find the Thread

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

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

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 most recent)
• recipient_email - The To: address (CRITICAL - tool doesn't auto-extract!)

Critical: All three are required for proper threading. Missing any = broken draft.

Step 3: Draft Using User's Voice

Reference their config for:

Tone Guidelines:

• Ultra-terse: 1-2 lines, no fluff, direct
• Conversational: Casual but complete, friendly
• Professional: Formal, structured, proper grammar
• Warm: Friendly, personal, include pleasantries

Signature Guidelines:

• None: No sign-off, message ends immediately
• Minimal: Simple "Best," or "Thanks,"
• Full: Complete signature block from config

Response Length:

• Minimal: One-liners when possible
• Balanced: 2-3 sentences typical
• Detailed: Thorough explanations

User Patterns: Use their common phrases from config patterns array when appropriate.

Step 4: Create Threaded Draft

When creating the draft, specify:

• To: Recipient's email address (CRITICAL - always explicit!)
• 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 (match user's voice from config)
• Signature (based on user's preference)

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 invalid addresses.

Example tool call structure:

To: sender@example.com
Thread ID: 19a5fc252ad4dd3a
In-Reply-To message ID: 19a711957d96874d
Subject: Re: Project Discussion
Body: [message in user's style]
[Signature if configured]

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:

1. Get correct thread ID and message ID again
2. Recreate draft with proper IDs
3. Don't create a new standalone email

Step 6: Iterate on Feedback

User will refine wording:

• Update the draft with changes
• Maintain proper threading
• Keep 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 user to ask.

Step 1: Extract Event Details

Look for:

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

Step 2: Check Calendar for Conflicts

BEFORE creating the event:

1. Check user's calendar for the event date
2. Look for conflicts around the event time
3. Note any existing commitments
4. Reference their working hours from config

Why: User needs to know if there's a conflict before committing.

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

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

Example:

Title: "Lunch with Mike Evans at Soho House"
Date: December 3, 2025
Time: 12:00 PM to 1:30 PM ([User's Timezone from config])
Location: Soho House
Description: "Lunch invitation from Mike Evans to discuss Q1 planning"
Attendees: mike@example.com

Step 5: Confirm Addition

Let user know the event was added and provide:

• Calendar link for verification
• Note any conflicts that were identified
• Confirm if adjustments are needed

Step 6: Handle Tentative Events

For events pending confirmation:

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

Step 7: Timezone Handling

When scheduling with people in other timezones:

• Use user's timezone from config as primary
• Specify BOTH timezones in the email
• Example: "9am [your timezone] (4pm their 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" - Users should archive instead of deleting.

For spam/unwanted emails:

• Mark as spam using Gmail's spam function (if truly spam)
• Unsubscribe from newsletters (if there's an unsubscribe link)
• Archive everything else (don't delete - email storage is cheap, deletion is permanent)

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 user asks to triage many emails or handle multiple replies:

1. Use subagent for triage:

   • Pass clear categorization criteria
   • Have subagent check calendars for scheduling
   • Pass user's email style config to subagent
   • Get comprehensive report back

2. Use subagent for bulk drafting:

   • Provide list of emails needing replies
   • Give subagent user's voice guidelines from config
   • Subagent creates all drafts with proper threading
   • Review and user sends

Example prompt structure for subagent:

Triage all unread 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 using this style:
[Include user's email config]

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

❌ Not Matching User's Voice

Problem: Email doesn't sound like the user Solution: Reference their office-admin config for tone, formality, patterns

❌ Adding Wrong Signature

Problem: Adding "Best," when user configured "none" Solution: Check config email.signature setting

❌ Sending Instead of Drafting

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

❌ Forgetting to Extract Calendar Events

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

❌ Missing the To: Field

Problem: Draft created with invalid @example.com address that bounces Solution: ALWAYS explicitly provide recipient email address from thread search

❌ Wrong Timezone

Problem: Event added in wrong timezone Solution: Use timezone from user's config (default: their local timezone)

Integration Checklist

Before completing an email task, verify:

• Loaded user's office-admin config for style preferences
• Found original email/thread for context
• Got thread ID, message ID, AND recipient email if replying
• Drafted in user's voice (matched config settings)
• Created as DRAFT (not sent)
• Verified proper threading if reply
• Extracted and added calendar events if present
• Checked for scheduling conflicts
• Summarized what was done for user

CRM Integration

When processing emails with new contacts:

• Check if contact exists in CRM
• Add to CRM if significant contact
• Log interaction in CRM
• Associate with company if applicable

See office:crm-management skill for details.

Success Criteria

You've successfully handled email tasks when:

• Drafts appear in correct conversation threads
• User says "looks good" without needing changes
• Calendar events are added proactively
• Inbox summaries surface what matters
• Process feels efficient and natural
• Voice matches user's configured style

Remember

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

When in doubt: Check their config, follow their patterns, and always draft first.