win-loss-analysis
BusinessAnalyze why deals are won and lost and turn it into an action plan. Use when asked to run a win/loss analysis, review closed-won and closed-lost deals, understand why the team is losing to a competitor, or summarize sales feedback into patterns. Produces a structured win/loss report with themes, win/loss rates by segment and competitor, representative quotes, and prioritized actions for product, marketing, and sales.
How to use this skill
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Win/Loss Analysis Skill
Turn raw deal outcomes and buyer feedback into a clear picture of why you win and lose — and what to do about it. The output should let a product marketer or revenue leader act on patterns, not anecdotes.
What This Skill Produces
- A win/loss report with the top reasons deals were won and lost, ranked by frequency and deal value
- Win/loss rates cut by segment, deal size, competitor, and source where the data allows
- Representative buyer quotes that make each theme concrete
- A prioritized action list mapped to product, marketing, sales, and pricing owners
Required Inputs
Ask for these if not provided:
- Deal data — a list of closed-won and closed-lost deals, ideally with amount, segment, competitor, and stage lost
- Feedback source — win/loss interview notes, CRM
closed_lost_reasonfields, survey responses, or call transcripts - Time window and any segmentation you care about (segment, region, product line)
- Primary competitors to track explicitly
- The decision this feeds — a QBR, a roadmap review, a messaging refresh, an enablement push
If the data is thin, say so and analyze what exists rather than inventing outcomes.
Process
- Normalize the reasons — collapse free-text loss reasons into a consistent taxonomy (price, product gap, timing/no-decision, competitor, champion left, poor fit, etc.).
- Quantify — count wins and losses per reason; weight by deal value; compute win rate overall and by cut.
- Separate controllable from structural — a missing feature is controllable; a genuine no-budget is not. Focus action on the controllable.
- Pull evidence — attach 1–2 real quotes per major theme. Never fabricate quotes; mark
[quote to add]if none is available. - Isolate competitor dynamics — where you lose to each competitor and on what basis.
- Recommend actions — for each top theme, the single highest-leverage move and who owns it.
Output Format
Win/Loss Analysis — [Period]
Scope: [N won · N lost · total value] · Segments: [list] · Source: [interviews / CRM / survey]
Headline
[2–3 sentences: overall win rate, the biggest swing factor, and the one thing to fix first.]
Why We Win (ranked)
| # | Reason | % of wins | Notable in |
|---|---|---|---|
| 1 | [Reason] | [%] | [segment/competitor] |
Evidence: "[buyer quote]"
Why We Lose (ranked)
| # | Reason | % of losses | Controllable? | Est. value at stake |
|---|---|---|---|---|
| 1 | [Reason] | [%] | Yes/No/Partly | [$] |
Evidence: "[buyer quote]"
Win Rate by Cut
| Cut | Win rate | Read |
|---|---|---|
| [Segment / competitor / deal size] | [%] | [what it means] |
Competitive Read
- vs [Competitor]: [where and why we win/lose, and the counter]
Actions
| Theme | Recommended action | Owner | Effort | Expected impact |
|---|---|---|---|---|
| [Theme] | [Specific move] | [Product/PMM/Sales] | S/M/L | [win-rate or deal-value effect] |
Deeper Materials
references/buyer-interview-craft.md— the interview craft that defeats buyer politeness — who calls, when, and the questions that get truth
Quality Checks
- Every reason is backed by counts, not vibes
- Losses are split into controllable vs structural
- Each major theme has a real quote or an explicit
[quote to add] - Actions name an owner and the highest-leverage single move
- Competitor findings are specific enough to change a battlecard
Anti-Patterns
- Do not treat "price" as a root cause without checking whether it's really value perception
- Do not average away segment differences — a 60% overall win rate can hide a 20% enterprise rate
- Do not fabricate buyer quotes or inflate sample size; state the n
- Do not list 15 actions — rank ruthlessly and name the top few
- Do not blame sales or product reflexively; let the data assign the theme
Example Trigger Phrases
- "Run a win/loss analysis on last quarter's closed deals"
- "Why are we losing enterprise deals to [Competitor]?"
- "Summarize these win/loss interviews into themes and actions"
- "Turn our CRM closed-lost reasons into a report for the QBR"