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Train Claude Cowork to Write Emails in Your Personal Style

Use Claude Cowork connectors to analyze your sent Gmail messages and create a reusable skill that drafts emails in your unique voice, tone, and structure.

Train Claude Cowork to Write Emails in Your Personal Style

Source episode · 18:37

How I AI: JJ Englert's Guide to a 'Daily Operating System' with Claude Cowork

with Claire Vo

18:37 to 24:21: JJ uses connected sent mail to identify his recurring tone and structure, then saves those patterns as a reusable Cowork email skill.

Read the full episodeWatch on YouTubeListen on SpotifyListen on Apple

Before you start

What you need

  • A representative set of sent messages from the connected Gmail account
  • Examples across common audiences and email types
  • Boundaries for phrases, tone, length, and details the skill must not invent

What you’ll make

A reusable Cowork skill that drafts new email from a brief while matching the owner's tone, structure, and level of directness.

Tools used

Step by step

The workflow

Follow the sequence once, then adapt the prompts, checks, and handoffs to your own setup.

3 steps

Step01

Enable Connectors

In Claude Cowork, open the Connectors settings and add an integration for Gmail. During setup, configure permissions to allow Cowork to read your sent emails for analysis. You can set other permissions, like requiring approval before sending, for safety.

Example prompt
In Claude Cowork, open the Connectors settings and add an integration for Gmail. During setup, configure permissions to allow Cowork to read your sent emails for analysis. You can set other permissions, like requiring approval before sending, for safety.

My actual values:
[insert the files, settings, accounts, or constraints for this step]

Give me the exact commands, settings, or output to use. Finish with a pass or fail check for enable connectors.
Step02

Prompt the Skill Creation

With the Gmail connector active, prompt Cowork to analyze your sent emails from a specific time period, like the last 30 days. Instruct it to create a reusable writing skill that captures your unique tone, vocabulary, and structure for future email drafting.

Example prompt
Hey, analyze my Gmail specifically the emails that I have sent in the last 30 days, and use this to create a writing skill specifically for emails that I write using, uh, my emails as an example of my writing structure. So whenever I want you to write an email in the future, you know exactly how I write my emails, and you'll use this skill.
Step03

Review and Refine the Outcome

Cowork will analyze your emails and generate a detailed style guide, saving it as a reusable skill in your project's memory. Review the generated skill to see if it accurately captures your voice. For safety, add a global instruction to your project telling Cowork to only write drafts and never send emails on your behalf.

Example prompt
Global Instruction: Never send emails or messages on my behalf. Always create a draft for me to review and approve first. This rule overrides any other instruction. [Add any other global project rules here]

What good looks like

  • Drafts resemble the owner's real emails without copying old private content
  • The skill adapts tone to the recipient and purpose
  • Names, commitments, dates, and facts come only from the supplied brief or connected context

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After the steps

Runbook notes

How to recover when the loop fails and where human judgment helps.

Recover

If it goes sideways

The skill learns one narrow email type as the entire voice
Analyze several audiences and purposes, then separate stable voice traits from situational patterns.
A draft invents a commitment or personal detail
Require a missing-information marker for unsupported facts and review recipients, dates, and promises before sending.

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