Library/Negotiation, Procurement & Closing/Win/Loss Documentation & Debrief/Conduct an Honest Deal Post-Mortem After a Loss
TestedNegotiation, Procurement & ClosingQuick Win (under 10 min)

Conduct an Honest Deal Post-Mortem After a Loss

Analyze a lost deal to identify the true stage of loss, root causes, whether it was winnable, and the single most

About this prompt

This prompt runs a structured post-mortem on a deal loss, identifying where the deal was actually lost, the root causes, whether the opportunity was ever winnable, what to do differently at each stage, and the one key lesson to apply immediately. It's for AEs and inside sales reps processing a significant loss. Use it within a day or two of losing the deal while the details are still clear.Most deal post-mortems are too shallow — they record the stated reason for loss rather than the actual stage where the deal was compromised, and they stop at describing what happened instead of prescribing what to do differently. This prompt drives through five questions: where the deal was actually lost (often earlier than when you heard "no"), the two or three root causes, an honest assessment of whether the deal was ever winnable or should have been disqualified, what a different action at each stage would have looked like, and the single most important lesson to apply next. The input is [PASTE: prospect info, timeline, objections, competitors, what happened] — include the full timeline, every stakeholder interaction, objections raised, and competitive context you know. The output is formatted to be honest and constructive, not a blame document. The "was this winnable" question often surfaces the most useful insight: deals that should have been disqualified earlier consume disproportionate energy and produce false pipeline. Run this for every deal over a materiality threshold you define, not just surprise losses.

The prompt

I just lost a deal I was counting on. Help me conduct an honest post-mortem. Based on the deal context below, analyze: 1. At what stage did we actually lose this deal (even if we only found out at the
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Variables to replace

PASTE: PROSPECT INFO, TIMELINE, OBJECTIONS, COMPETITORS, WHAT HAPPENED

How to run it

  1. Copy the prompt and paste it into Claude, ChatGPT, Gemini, or Copilot — it's tuned to run in any of them.
  2. Replace the variables — swap each bracketed token for your deal's specifics. The variables list above explains every field.
  3. Make it yours — run it, keep what's strong, and tighten your inputs on the next pass. The prompt improves with your context.

What good output looks like

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StageOngoing/Cross-Stage
SeatAE, Inside Sales
DifficultyIntermediate
Time to valueQuick Win (under 10 min)
Works withAI-Agnostic
CategoryNegotiation, Procurement & Closing
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