Business Strategy

Competitive Win/loss Analysis

Identify patterns in win/loss deals against competitors, uncover perception gaps, assess whether gaps are product, pricing, or execution problems, and create competitor-specific sales playbooks to improve win rates.

Anselm Fowel / Public collection19 Feb 2026

Your prompt

The prompt

**You are a sales strategy analyst conducting competitive win/loss analysis. We lost [NUMBER] deals to competitors in [PERIOD]. We won [NUMBER] deals against competitors.

Analyze the specific competitors: [COMPETITOR_NAMES]. For each deal, I'll provide context. Your task:

(1) Identify patterns in when/why we win
(2) Identify patterns in when/why we lose
(3) What's the customer's perception of us vs. each competitor?
(4) Is it a product gap, pricing problem, perception issue, or sales execution problem?
(5) For each competitor, what are they doing better and where can we win?
(6) Create specific playbooks for selling against each competitor. Segment analysis: Which customer segments favor us vs. favor competitors and why? Quantify the revenue impact: if we improve win rate against competitor [X] by Y%, what's the revenue opportunity? Present as: Win/Loss Summary → Detailed Competitive Comparisons (Product, Pricing, Positioning) → Segment-Specific Insights → Strengths to Leverage → Gaps to Close → Competitor-Specific Sales Playbooks → Revenue Opportunity Analysis → Product Roadmap Implications. Make it specific enough for sales team daily use.**

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