This AI prompt helps you get someone to say yes without pushing them. It asks you 2 questions about the person first, then builds your ask around a question they answer, names their objection before they can & gives them 2 ways to say yes.

The prompt that wins a yes without pushing

It’s Friday. You want out by 3 & the only person who can cover the desk is Sam.

So you do the lazy thing. You open the chat & type “Come up with something good to convince Sam to cover for me.”

It writes, “3 reasons Sam should say yes.” A closer so sure of itself you almost laugh.

You’d never say a word of it out loud. It sounds like a telemarketer selling you life insurance.

And people agree more when the whole thing feels like their idea.

That’s why this prompt skips the pitch.

It builds the ask around a question Sam answers, names the objection before they can & gives them 2 ways to say yes that work for everyone.

I need to get [person, like my manager or my partner] to [do the thing]. They haven't said yes yet.

First, ask me 2 things, then wait for my answer:
1. How big is the ask, and have we disagreed about it before?
2. Who is this person to me, a partner, a coworker, a friend? The same words land differently depending on that.

Then build the approach on how people actually agree to things:
- Open with a calibrated question, one that starts with "how" or "what" and makes them help solve my problem ("how am I supposed to get this done by Friday and still cover the desk?"). Never one they can answer with a flat "no."
- Name their likely objection before they raise it, so it loses its charge.
- Give them 2 options that both work for me instead of one demand. People move faster when the choice feels like theirs.

Give me 3 things I could actually say, shortest to longest, matched to who this person is to me. Tell me which to open with. Then a fallback if they still balk, the smallest yes that keeps things moving, not the whole ask at once.

Why it works: It asks 2 questions before writing anything, so the ask fits the actual person instead of a stranger. The calibrated question gives them your problem to solve instead of something to push back on. Naming the objection first takes the air out of it.

One gap: That same move backfires if you guess the objection wrong. Tell Sam “you probably think this is too much to ask” & you’ve just given them a reason they hadn’t thought of.

Simple fix: Tell it to open with the question & hold the objection line until you’ve heard their real one.

When the ask is harder than a favor

If the ask could turn into an argument, the hard conversation prompt gets you ready for it. If you’re asking in writing, the email reply prompt writes back with one goal in mind. For a sit-down, the meeting prep prompt helps you think through their side first.

This prompt first ran in issue 9.