The Build
Phase 1: AI Email Triage System
We built a custom AI-powered email assistant that monitors the senior leader's Outlook inbox 24/7, automatically categorizes every incoming email, and delivers actionable briefings three times per day plus real-time urgent alerts.
How It Works
Every new email is analyzed by Claude AI via a Zapier automation workflow. The system:
Categorize the Email
Labels the email using pre-set categories like Senior Leadership, Board Communication, Parent Concern, etc.
Assigns Priority
Groups the email into Urgent, High, Medium, or Low priority based on sender, content, and context.
Generates AI Summary
Provides an AI summary of the email's content and what's being asked and the required next steps.
Writes Draft Reply
AI drafts a reply in the senior leader's voice based on extensive training, ready to approve and send.
Recommends Action
AI provides a suggested action or next step for the email, like "Handle directly" or "Forward to IT."
AI Training & Customization
Before the system went live, we trained the AI to understand three critical dimensions of the senior leader's communications:
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Organizational Context
The AI learned the school's structure: who reports to whom, what issues go to which stakeholders, and how different sender types (board vs. parents vs. vendors) require different handling. This allows the system to make intelligent delegation recommendations based on organizational hierarchy, not just generic "forward to someone" suggestions.
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Communication Patterns
We analyzed the leader's existing email patterns to identify what signals "urgent" vs. "routine" in this specific context. For senior leadership at an independent school, an email from a board officer about budget approval is urgent. An email from a parent about carpool procedures is not. The AI learns these nuances through custom prompts that encode institutional knowledge. The senior leader also provided a list of VIP senders who should always trigger an "Urgent" alert, helping him gain visibility on the communications that matter most.
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Writing Style & Voice
Draft replies aren't generic AI-generated text—they're written in the senior leader's actual voice. We provided the AI with examples of his email style (tone, sentence structure, typical sign-offs, level of formality) and built custom prompts that replicate his communication style. This makes the AI's draft replies sound like they came from him, not a robot.
This training happens during the first 1-2 weeks of Phase 1 implementation, with ongoing refinement as the system processes real emails and learns from feedback.
Three Daily Briefings
Instead of checking email constantly, the senior leader receives structured briefings at:
Review overnight emails before the day starts
Catch up on morning activity and plan for the afternoon
Clear afternoon emails before heading home
Each briefing shows a prioritized list of emails with summaries, suggested actions, and pre-written draft replies with one-click action buttons that allow him to send the draft reply, edit the message, dismiss the email, or mark it as handled.
Example morning briefing showing prioritized emails with AI summaries and one-click action buttons
Real-Time Urgent Alerts
Emails from a custom list of VIP senders (board officers, senior leadership, direct reports) trigger immediate notifications so there is no waiting for the next scheduled briefing. Critical issues surface instantly through a real-time urgent email alert.
Real-time urgent alert triggered by email from board member
One-Click Actions
Every email includes four action buttons:
✅ Approve & Send
Sends the AI-generated draft reply (with an added confirmation step to prevent accidental replies)
✏️ Edit Draft
Opens the draft in Outlook for manual editing before sending
❌ Dismiss
Removes the email from the queue and marks it as read in his inbox (no action needed)
🔧 Mark as Handled
Flags the email as handled and marks it as read if already replied to manually
Confirmation screen ensures no accidental replies from Outlook preview
All four action buttons pop a confirmation screen for users to click before the AI takes any action. This helps prevent premature replies from clicks and prevents accidental replies from Outlook's preview function.
Human-in-the-Loop Design: No emails are ever sent automatically. Every reply requires explicit approval. The AI handles triage and drafting; the human makes the final call.
Phase 1 streamlined email management. The senior leader went from manually triaging 42+ emails/day to reviewing structured briefings with pre-written replies. Hours reclaimed, urgent issues surfaced automatically, and high-priority items now visible at a glance.
