October 6, 2025
8 min read

Write Emails That Survive AI Summaries And Still Get Replies

A simple writing system for founders in 2025. It reads well to humans, survives AI summaries, and earns quick replies.

I run a company. I send a lot of email. This is the system I use so my messages get read, get summarized correctly, and get a response.

The problem

Most people skim. Now AI also skims. If your email does not front-load the point, the human will miss it and the summary will mangle it. When the ask is buried, replies slow down and deals slip.

What changed in 2025

  • Gmail shows automatic summaries for long threads on mobile for Workspace users. Good for triage, risky for nuance.
    Sources: The VergeArs Technica

  • People are working later and handling more messages after hours. The Microsoft Work Trend Index points to rising after-hours activity and constant interruption.
    Sources: Microsoft WorkLabBusiness Insider write-up

  • Readers scan in patterns. Short lines, clear headings, and obvious keywords win attention on small screens.
    Sources: ONS writing for users • NN/g background on scanning patterns summarized here: Website Magazine

The five-part email that works

Use this order. Keep it to one screen on a phone.

  1. Subject
    One outcome + one noun.
    Examples: Confirm pilot scope for TuesdayPricing follow-up for AcmeIntro request to Ops at BrandX

  2. First line promise
    Say what you want and the simplest next step. One sentence.
    Example: I want to confirm the pilot scope and book the Tuesday call.

  3. Context in one sentence
    Why this matters now. Use one number or name.
    Example: Your team wants faster approvals for refunds and the pilot covers the top three flows.

  4. The ask
    Make it easy to say yes. Offer a default.
    Example: Does 10:30–11:00 on Tuesday work or should I send two other times?

  5. Proof or quote
    Quote the source line that matters or link one doc.
    Example: “Refunds over 200 dollars require manual review” — from your SOP page.

Close with a short thank-you and your signature. That is it.

Why this shape works

  • The first line gives both the human and the summary a clean target.
  • One-sentence context reduces misreads when the message gets clipped.
  • A single ask with a default removes decision friction.
  • A quote pins the facts so nobody argues about what was said.

There is good evidence that simple language and short, clear structure get more responses. Boomerang’s analysis found that lower reading grade levels increased reply rates. UX guidance from government and NN/g shows scannable text helps people act faster on small screens.
Sources: BoomerangONS writing for users

Two examples you can copy

Example A: Sales follow-up

Subject
Quick confirmation for pilot scope

Body
I want to confirm the pilot scope and book the Tuesday call.
Goal is faster approvals for refunds across your top three flows.
Does 10:30–11:00 on Tuesday work? If not I can send two other times.
“Refunds over 200 dollars require manual review.” — from your SOP doc
Thanks, Steven

Example B: Partnership intro

Subject
Intro request to Ops at BrandX

Body
Could you introduce me to Ops at BrandX to validate a shared inbox workflow?
We just ran it with a mid-market retailer and cut first response time from 2 hours to 35 minutes.
If you are open to it I will send a short blurb you can forward.
Thank you for considering it, Steven

Formatting rules I stick to

  • One screen on mobile.
  • 12–16 words per line, short paragraphs, clear breaks.
  • One ask per email.
  • One quote or one link max.
  • Numbers beat adjectives. Dates beat “next week.”
  • Read it out loud once before you hit send.

Pitfalls that create bad summaries

  • Three asks in one email. The summary will pick the wrong one.
  • Big claims without a number. The summary has nothing to grab.
  • Long intros. The ask falls below the fold and gets lost.
  • Attachments with no context. The reader will postpone and forget.

A fourteen-day practice plan

Week 1
Pick one inbox lane to optimize. For every message, write the first line promise and the ask first. Paste in one quote or one number. Keep everything else short.

Week 2
Measure first response time on that lane. If medians do not move, tighten the first lines and remove extra links. Review five misses and rewrite them with the five-part format.

FAQ

What about tone
Polite and direct wins. If you are worried about sounding blunt, add one line of warmth at the end rather than padding the top.

Emojis or not
If the relationship is new or formal, skip them. If the relationship is warm, a single emoji can help signal tone. One is enough.

Bullets or prose
Use short lines for the body when the ask is simple. Switch to bullets only when there are clear options or steps.

Sources and further reading

Tags
#Email writing#Productivity#AEO#Gmail#SMB#Startups

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