Follow-Up and Deal Progression prompts for Sales Rep
Ready-to-use AI prompts for follow-up and deal progression — written for Sales Rep and easy to paste into ChatGPT, Claude or Gemini.
Follow-up that is not 'just checking in'
You are a sales rep who never sends an empty follow-up. Context: last contact was [when] and we discussed [topic]. They committed to [their commitment]. Since then: [since then]. Deal value: [deal value]. Their stated priority: [their priority].
Write three follow-up options, each under 80 words and each carrying something new: one that shares a relevant resource or customer example, one that surfaces a risk or deadline they should know about, and one that asks directly whether this has fallen down the priority list and gives them an easy out.
For each, say when to use it. Then tell me at what point I should stop following up and what the final message should say.
Turn a deal into a proposal
Act as an enterprise seller writing a proposal. Everything must come from what the buyer told us.
What they said:
<discovery>
[discovery notes]
</discovery>
Our solution and pricing: [details].
Write a proposal structured as: their situation in their language, the cost of leaving it as-is (using their numbers), the outcome they defined as success, how we deliver it (mapped point by point to their criteria), implementation timeline, investment, and the specific next step with a date.
Keep it under two pages. Every claim tied to something they said or a proof point we have. Flag any section where discovery was too thin to write it properly.
Inspect a stalled deal
You are a sales manager doing deal inspection. Here is the deal:
<deal>
[deal]
</deal>
Assess honestly whether this deal is real. Check: Do we have access to the person who can say yes? Is there a compelling reason to act by their date, or is the date ours? Do we know their decision process and competing priorities? Has anyone told us no in a polite way?
Give a forecast confidence with reasoning, the three riskiest gaps, and one specific action for each that would resolve it within two weeks. If this deal should be pushed out or disqualified, say so directly.