Three Things AI Can Do to Your Email

Alexandra Samuel counts three ways to write with AI.

She writes about working with technology for Harvard Business Review and the Wall Street Journal. The three-way split is hers, while which one I'd reach for, and when, is my own view.

"Write it for me" isn't on her list, though that one works too, in a way.

Type "Write an email to my landlord about the boiler", and you'll get a decent email with your name at the bottom and nothing of you in it. Do that for a year, and you can no longer write the email yourself.

Picture the email you've been putting off, the slightly awkward one to someone who matters. The cursor is hovering over the box.

1. Organise what you want to say. Hand over the mess, every point and every worry, in no order. You get back a shape, which means what goes first and where the tricky bit sits. Every sentence is still yours, because AI never touches the words.
2. Draft the one sentence you can't get right. Maybe that's the line that says no without offending, or the opening that has to be direct without sounding cold. You write the rest, and leave a gap where you're stuck.
3. Critique the draft once it's finished. The AI reads it the way a careful reader would. It points out where they'd stumble, such as the tone or a sentence that could be read two ways. What to change is still your call.

For an awkward, important email like the one you're picturing, use all three, in that order. For a routine email, use the third, or none.

Start with the mess, typed straight in.

I need to write an email. Here's everything in my head about it, in no order. [dump it all] Don't write the email. Tell me what order the points should go in, which ones to cut, and where the awkward part should sit. Then stop and let me write it.

For the second use, write the email yourself and mark the gap with something like [DECLINE POLITELY HERE].

Here's my draft with a gap marked. Give me three versions of the sentence for that gap, each in a different tone. Make one warm, one neutral and one firm. Keep each to one sentence. Don't touch anything else.

Pick one, or join the best halves of two, and then read the whole email out loud. Does the new sentence sound like the rest of you?

For the third use, paste in the finished draft before you send it.

Here's an email I'm about to send to [who, and the relationship]. Read it as they would. Tell me three things. First, the one line most likely to be misread. Second, anything I've left out that they'll need. Third, whether the tone matches what I'm trying to do, which is [what]. Don't rewrite it.

Often a full rewrite comes back anyway, so ignore the rewrite and ask again with something like "I didn't want a new version. What's wrong with mine?"

Watch the gaps in the second use. Drafting one hard sentence and drafting the whole email are closer than they look, and three hard sentences already make half an email that isn't yours.

If the gaps are multiplying, stop and write the email badly yourself. A clumsy email you wrote usually lands better than a smooth one you didn't.

"Most of my emails don't deserve this." Agreed.

Let AI write the meeting confirmation and the reminder about an unpaid invoice, because nobody will care.

Keep the three uses for emails where the person reading would notice the difference between you and a machine. Those emails are rarer than you'd think, and they matter more.

If the awkward one has been sitting in drafts for days, start by deciding what you want from it.

Credit goes to Alexandra Samuel for the three uses (organise, draft the hard small bits, critique), from "Should You Write with Gen AI?" in Harvard Business Review (December 2024). Read the article for her full reasoning.