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Learn Your Email Style, Auto-Draft Replies

Read past sent emails, learn tone & structure, save as a reusable style guide, then draft replies in your voice.

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Email Operations
Underwriters, account managers, sales — anyone with a high-volume inbox
Outlookemail draftingstyle guideplaybooks

The problem

  • Generic AI-drafted emails read like AI. Underwriters don't send them.
  • Each underwriter has personal phrasing, salutations, sign-offs, and risk-of-the-week language.
  • Brokers expect a specific cadence — too short feels rude, too verbose buries the answer.

How InsightWorker handles it

1
email-style-learn skill samples your last 50 sent emails from Outlook. email-style-learn skill · search_emails
2
Extract tone, salutations, sign-offs, sentence rhythm, vocabulary, structure preferences. agent reasoning
3
Save findings to .insightworker/playbooks/email-style.md — reusable across drafts. edit_file
4
When a new email arrives, email-draft-reply loads your style + the source + context, drafts the reply. email-draft-reply skill
5
Draft is saved as markdown for you to review — never auto-sent. send_email always permission-prompts. send_email (permission-gated)

Sample prompt

"Learn my style from my last 50 sent items, then draft a reply to the latest from broker@acme."
Deliverables: .insightworker/playbooks/email-style.md · drafts/email/<date>-<slug>.md
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