Library/Negotiation, Procurement & Closing/Win/Loss Documentation & Debrief/Generate a Monthly Win/Loss Pattern Report
TestedNegotiation, Procurement & ClosingQuick Win (under 10 min)

Generate a Monthly Win/Loss Pattern Report

Analyze 30 win/loss summaries to surface the top three win patterns, top three loss patterns, and the single

About this prompt

This prompt helps sales managers and RevOps teams extract structured insight from a month's worth of win/loss summaries, producing a concise one-page report with clear patterns and a prioritized action item. It also flags whether patterns are shifting versus prior months, which is the signal most manual reviews miss. Use it at the end of each month before pipeline and forecast reviews.Win/loss patterns that live in individual deal notes never aggregate into actionable insight — managers read the summaries, form impressions, but rarely surface statistically reliable patterns or spot when those patterns are changing. This prompt takes up to 30 win/loss summaries pasted into [ALL WIN/LOSS SUMMARIES], analyzes them for recurring win conditions and loss triggers, and formats the output as a one-page monthly insights report suitable for a leadership review. The prompt specifically asks the AI to flag trend changes versus prior months, which requires you to either include context about prior period patterns or paste both months' summaries for comparison. Use this prompt at the end of each month for a standard operating cadence — not as a one-time diagnostic, since the pattern identification improves when the AI can compare across time periods. For best results, include loss notes even when the rep's explanation is 'price' or 'lost to competitor' without detail: the AI can often identify secondary patterns in how those deals were described that reveal a more specific root cause than the stated reason.

The prompt

Analyze these 30 win/loss summaries from last month. Identify: top 3 win patterns, top 3 loss patterns, whether those patterns are changing vs. prior months, and the single highest-leverage improveme
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Variables to replace

PASTE ALL WIN/LOSS SUMMARIES

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

StagePipeline Management
SeatSales Manager, Sales Director, RevOps / Sales Ops
DifficultyAdvanced
Time to valueQuick Win (under 10 min)
Works withAI-Agnostic
CategoryNegotiation, Procurement & Closing
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