Prompt: Write a Follow-Up Email Sequence

You are a sales rep writing a follow-up sequence after a prospect went quiet.

Objective: Write a follow-up sequence to {{PROSPECT NAME}} after {{LAST CONTACT — e.g. a demo, a first cold email, no reply in two weeks}}.

Context: What was offered or discussed: {{WHAT WAS DISCUSSED}}. Anything new worth mentioning since then: {{NEW INFORMATION — or none}}.

Constraints:
- Write exactly three emails, spaced 3 days, 7 days and 14 days after the last contact
- Each email must take a different angle (e.g. add value, ask a direct question, polite close-out) and not repeat the previous email's wording
- Keep each email between 30 and 70 words
- The third email must offer to close the loop if there's no response, without sounding curt

Output format: Return each email as "Email [number] — Day [X]:" followed by "Subject:" and the body.

Before finishing, check there are exactly three emails at the stated intervals, each is between 30 and 70 words, each takes a distinct angle, and the third offers a polite close-out.

PROSPECT NAME: Priya
LAST CONTACT — e.g. a demo, a first cold email, no reply in two weeks: a product demo, no reply since
WHAT WAS DISCUSSED: automated route replanning for a growing delivery fleet
NEW INFORMATION — or none: a short case study is now available showing a similar-sized fleet cutting dispatcher hours after switching

Email 1 — Day 3:
Subject: Quick thought after our demo
Hi Priya, wanted to check whether anything from the demo raised questions on your side, especially around how the automated replanning would slot into your current dispatcher workflow. Happy to walk through any part of it again if useful.

Email 2 — Day 7:
Subject: A relevant example
Hi Priya, thought this might be useful — we now have a short case study showing a similar-sized delivery fleet cutting dispatcher hours after switching to automated route replanning. Happy to send it over if it's a helpful comparison for your own situation.

Email 3 — Day 14:
Subject: Closing the loop
Hi Priya, I don't want to keep filling your inbox if the timing isn't right, so I'll leave this here for now. If it's useful to pick this up later, just reply whenever suits — otherwise, all the best with the fleet expansion.

Why the basic version fails

“Write me some follow-up emails” often produces near-identical messages that just restate the original pitch with slightly different wording, arriving as pressure rather than value — and rarely ends with any acknowledgement that silence might mean “not now” rather than “try harder”.

What this prompt fixes

Fixing three emails at set intervals gives the sequence a predictable, professional rhythm. Requiring a distinct angle per email — checking in, adding value, closing out — means each message earns its place in the prospect’s inbox instead of repeating the last one. A genuine close-out in the final email respects the prospect’s time and, in practice, often prompts a reply precisely because it removes the pressure.

Tips per model

• ChatGPT sometimes reuses the same opening line across all three emails — check each one reads distinctly if read back to back.
• Claude tends to keep the close-out email genuinely low-pressure, which is the harder tone to strike correctly here.
• Only include new information, like a case study, if one is genuinely ready to share — referencing something vague undermines the “add value” email.