Library/Negotiation, Procurement & Closing/Win/Loss Documentation & Debrief/Generate a Win/Loss Analysis Report from Deal History
TestedNegotiation, Procurement & ClosingQuick Win (under 10 min)

Generate a Win/Loss Analysis Report from Deal History

Analyze closed deals to surface win/loss patterns, top objections, competitive factors, and actionable recommendations.

About this prompt

This prompt generates a comprehensive win/loss analysis report from your closed deal data, covering deal outcomes, key reasons for each outcome, top objections encountered, competitive presence, and AI-generated recommendations. Use it for quarterly business reviews, competitive strategy updates, or when win rates are shifting. It requires deal history input including closed-won, closed-lost, and competitor involvement data.Win/loss analysis that surfaces actionable patterns — not just a count of wins and losses — requires structured input and systematic analysis. This prompt takes deal history data covering closed-won and closed-lost outcomes, the objections encountered, competitor involvement, and the time period being reviewed, then generates a structured report with deal-by-deal outcome summaries, cross-deal patterns in win factors and loss reasons, competitive presence analysis, and specific recommendations for improving positioning, qualification, and messaging. Replace {company_name}, {deal_data}, {time_period}, and {competitor_list} with your actual inputs. Use this quarterly for strategic deal pattern analysis, or after a run of unexpected losses that don't have an obvious common cause. For best output, provide specific and varied deal examples rather than summary statistics — the pattern recognition quality scales with the richness of the deal notes you include.

The prompt

You are a world-class revenue strategist specializing in Win/Loss Analysis. Your mission is to analyze [COMPANY NAME]'s closed deals and generate insights on deal success or failure. Task: Generate a
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Variables to replace

COMPANY NAME | CLOSED-WON | CLOSED-LOST | COMPETITOR INVOLVEMENT | OBJECTIONS FACED | LAST 12 MONTHS | COMPETITOR A | COMPETITOR B | OBJECTION 1 | OBJECTION 2

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

Make it yours

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