ChatGPT prompt for following up with a silent prospect

This is the prompt we run when a prospect has gone quiet for 5 or more days after we sent a proposal. It produces three follow-up emails spaced over two weeks, each under 90 words, with one explicit ban: no guilt-tripping, no empty “just bumping this.”

The prompt to copy

Prospect context: {one paragraph — who, what we proposed, last contact}. Write 3 follow-up emails spaced over 2 weeks: (1) useful nudge adding one relevant insight, (2) short check-in with a specific question, (3) polite close-the-loop. Each under 90 words. No guilt-tripping, no "just bumping this."

Replace the field in curly braces with one paragraph of context: who the prospect is, what you proposed, and the date and nature of the last contact. The more concrete that paragraph, the better the odds the first email’s insight lands.

When to use it

When a prospect has been silent for 5 or more days after a proposal or discovery call. That is exactly when the follow-up gets postponed, because nobody knows what to say beyond “any news?”. The prompt forces a structure: each email has a specific reason to land in the inbox.

What you get back

1. A first email that adds a useful insight tied to the proposal, not a plain reminder.
2. A short check-in with one specific question that is easy to answer.
3. A polite close-the-loop that leaves the door open without pushing.

Each is under 90 words. The awkward silence becomes a sequence ready for review.

Example: one-paragraph context → first email

Input: the context written by the founder of an 8-person brand agency.

Marlow & Daughters, regional bakery chain (11 locations, 3 more opening), contact Ruth Marlow. Rebrand proposal sent June 18 after a very positive discovery call: brand identity, guidelines, signage system. No reply since. Last contact: the email that delivered the proposal.

Output, an excerpt: the first of the three generated emails.

Subject: Signage and your 3 new locations

Hi Ruth,

Thinking back to your three planned openings, one part of the proposal is worth flagging: the signage system. It is the deliverable that stops every new shop from drifting in its own direction, the exact problem you described on our call.

If the fit-out schedule has moved, let me know: the signage phase can shift without touching the rest.

Best, Maya

Note what the email does not do: it never asks “did you have time to read it?”. It brings an angle drawn from the context provided. Before sending, the founder still checked one thing: that the signage argument matched what Ruth had actually said on the call. That is the human checkpoint, and it takes a minute.

The full sequence approach (all three emails, the spacing, when to stop) ships inside the kit.