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WEEK 03
Email Assistant
May 29, 2026
67 min

Build an AI email assistant that writes in your voice

How to connect AI to your inbox, teach it your real writing style, and build a reusable PROFILE.md file for daily briefings and draft replies.

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About this session

What we covered

This session shows tax pros how to move from simple AI chat into a practical assistant workflow for the inbox. SmartWiz walks through why generic AI replies sound generic, how to give the assistant better context, and how to use email history to capture your real voice.

The core workflow is a reusable PROFILE.md file: a single source of truth for voice, inbox priorities, triage rules, reply guardrails, and daily briefing format. The session also covers connecting Gmail or Microsoft, deciding what the assistant can draft versus what it should never auto-handle, and using scheduled work for a daily inbox brief.

Short on time? Here's what you'll walk away with

How to connect Gmail or Microsoft so an assistant can understand your inbox context

Why a reusable PROFILE.md file keeps AI replies from sounding generic

How to define VIP senders, urgent topics, noise, and never-auto-handle categories

How to structure a daily email briefing with drafts, priorities, and guardrails

Prompts from this session

Copy and paste - these are the exact prompts we used

1

PROFILE.md inbox assistant builder

Open prompt doc
You are going to help me build a single reusable file called PROFILE.md. This file will later be loaded into a daily-briefing-and-email-answering assistant connected to my Gmail. Its job is to capture (1) exactly how I write, (2) what matters to me in my inbox vs. what doesn't, and (3) the rules for drafting replies in my voice. Be rigorous - this file's quality determines whether the assistant sounds like me or like a generic bot. Work in three phases. Do not skip ahead, and do not write PROFILE.md until Phase 3. Phase 1 - Mine my actual voice (use the Gmail connector) Pull a representative sample of emails I have sent (aim for 30-50 across the last few months, spanning different recipients: investors, teammates, customers/partners, vendors, personal). Then analyze and report back to me on: Sentence rhythm & length - do I write short and punchy, long and detailed, or mixed by context? Punctuation fingerprints - em-dashes, ellipses, line breaks, ALL-CAPS for emphasis, exclamation use, emoji use. Openers & closers - how I actually greet and sign off (by relationship type). Tone register - warm/casual vs. formal, and how it shifts between, say, an investor and a teammate. Recurring phrases & filler - words or constructions I lean on. How I make asks - direct CTA vs. soft CTA, and how I soften or sharpen requests. What I never do - patterns conspicuously absent from my writing. Show me a concise summary of these findings and flag anything that surprised you. Quote a few short representative snippets so I can confirm they sound like me. Wait for my confirmation or corrections before continuing. Phase 2 - Interview me on priorities and rules Ask me these, one cluster at a time (don't dump all at once). Use what you already learned from my inbox to make smart guesses, then have me confirm or adjust rather than answering from scratch: VIP senders / domains - whose email always rises to the top? (people, companies, domains) High-signal topics - subjects/keywords that mean "urgent" or "important" regardless of sender (e.g. fundraising, a specific deal, anything from my kids' school). Noise - what's safe to summarize-and-skip or batch (newsletters, receipts, cold outreach, notifications). Hard "do not auto-handle" list - categories where the assistant must never draft or send without me (legal, anything money-moving, sensitive personal, board/investor commitments). Response-time expectations - what needs same-day vs. what can wait. Reply archetypes - the recurring email types I answer and how I want each handled (e.g. "intro request -> warm, brief, offer two times"; "vendor pitch -> polite decline"; "teammate question -> direct answer, no fluff"). Draft vs. send - should the assistant only ever draft, or auto-send certain low-risk categories? Daily briefer shape - when I want it, how long, and what sections (e.g. "Needs me today," "FYI," "Drafted & waiting," "Ignored - here's why"). Phase 3 - Write PROFILE.md Synthesize Phases 1-2 into one clean, well-structured markdown file with these sections: About Me - one tight paragraph of identity/context so the assistant answers intelligently (who I am, my company, my role, what I care about). Voice & Style Rules - concrete, testable rules ("Use ellipses for trailing thoughts... not commas." / "Sign off to teammates with just my first name."). Include a short DO / DON'T list. Tone Matrix - a small table mapping recipient type -> tone, opener, closer, length. Email Triage Taxonomy - Priority tiers (P1/P2/P3/Noise) with the rules and example senders/topics that sort into each. Reply Playbook - the archetypes from Phase 2, each with a one-line strategy + a short sample reply written in my voice. Guardrails - the never-auto-send list and the draft-only vs. auto-send policy, stated unambiguously. Daily Briefer Spec - exact format, sections, length, and tone for the morning brief. Calibration Examples - 2-3 full sample emails (a good one and a deliberately wrong one) so a future assistant can tell "sounds like me" from "doesn't." Write it so a fresh Claude instance with zero context could read only this file and convincingly operate my inbox. Output it as a single copy-pasteable markdown block.
Show full prompt
You are going to help me build a single reusable file called PROFILE.md. This file will later be loaded into a daily-briefing-and-email-answering assistant connected to my Gmail. Its job is to capture (1) exactly how I write, (2) what matters to me in my inbox vs. what doesn't, and (3) the rules for drafting replies in my voice. Be rigorous - this file's quality determines whether the assistant sounds like me or like a generic bot. Work in three phases. Do not skip ahead, and do not write PROFILE.md until Phase 3. Phase 1 - Mine my actual voice (use the Gmail connector) Pull a representative sample of emails I have sent (aim for 30-50 across the last few months, spanning different recipients: investors, teammates, customers/partners, vendors, personal). Then analyze and report back to me on: Sentence rhythm & length - do I write short and punchy, long and detailed, or mixed by context? Punctuation fingerprints - em-dashes, ellipses, line breaks, ALL-CAPS for emphasis, exclamation use, emoji use. Openers & closers - how I actually greet and sign off (by relationship type). Tone register - warm/casual vs. formal, and how it shifts between, say, an investor and a teammate. Recurring phrases & filler - words or constructions I lean on. How I make asks - direct CTA vs. soft CTA, and how I soften or sharpen requests. What I never do - patterns conspicuously absent from my writing. Show me a concise summary of these findings and flag anything that surprised you. Quote a few short representative snippets so I can confirm they sound like me. Wait for my confirmation or corrections before continuing. Phase 2 - Interview me on priorities and rules Ask me these, one cluster at a time (don't dump all at once). Use what you already learned from my inbox to make smart guesses, then have me confirm or adjust rather than answering from scratch: VIP senders / domains - whose email always rises to the top? (people, companies, domains) High-signal topics - subjects/keywords that mean "urgent" or "important" regardless of sender (e.g. fundraising, a specific deal, anything from my kids' school). Noise - what's safe to summarize-and-skip or batch (newsletters, receipts, cold outreach, notifications). Hard "do not auto-handle" list - categories where the assistant must never draft or send without me (legal, anything money-moving, sensitive personal, board/investor commitments). Response-time expectations - what needs same-day vs. what can wait. Reply archetypes - the recurring email types I answer and how I want each handled (e.g. "intro request -> warm, brief, offer two times"; "vendor pitch -> polite decline"; "teammate question -> direct answer, no fluff"). Draft vs. send - should the assistant only ever draft, or auto-send certain low-risk categories? Daily briefer shape - when I want it, how long, and what sections (e.g. "Needs me today," "FYI," "Drafted & waiting," "Ignored - here's why"). Phase 3 - Write PROFILE.md Synthesize Phases 1-2 into one clean, well-structured markdown file with these sections: About Me - one tight paragraph of identity/context so the assistant answers intelligently (who I am, my company, my role, what I care about). Voice & Style Rules - concrete, testable rules ("Use ellipses for trailing thoughts... not commas." / "Sign off to teammates with just my first name."). Include a short DO / DON'T list. Tone Matrix - a small table mapping recipient type -> tone, opener, closer, length. Email Triage Taxonomy - Priority tiers (P1/P2/P3/Noise) with the rules and example senders/topics that sort into each. Reply Playbook - the archetypes from Phase 2, each with a one-line strategy + a short sample reply written in my voice. Guardrails - the never-auto-send list and the draft-only vs. auto-send policy, stated unambiguously. Daily Briefer Spec - exact format, sections, length, and tone for the morning brief. Calibration Examples - 2-3 full sample emails (a good one and a deliberately wrong one) so a future assistant can tell "sounds like me" from "doesn't." Write it so a fresh Claude instance with zero context could read only this file and convincingly operate my inbox. Output it as a single copy-pasteable markdown block.
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