Win/Loss Interview

Every lost deal contains two stories: what the rep thinks happened, and what actually happened. They almost never match. Reps rationalize losses to protect their self-model — "we lost on price," "their timeline slipped," "they went internal." These explanations feel true because they're unfalsifiable. Real win/loss work reads the behavior: what did the buyer do, when, and in what sequence? A buyer who "went with a competitor for price" but never asked for your best price didn't lose on price — they lost interest and needed an exit line. A buyer who "went internal" but was active until the legal review started lost in legal, not to an internal option. Paste this prompt into Claude or ChatGPT. Share deal notes for one deal (deep diagnosis) or multiple deals (pattern analysis). The AI reads behavior against stated reason, names the actual cause, and gives one specific process change per root cause.

1. Click "Copy prompt" above and paste it into Claude or ChatGPT to start the session.
2. For each deal, share: buyer profile (role, company size, industry), deal size and stage when it ended, what the rep said the reason was, what happened in the last 3 interactions before it ended, what the rep had implied the product would solve, and which competitor won if known.
3. For a single deal: you'll get a full diagnosis block — stated reason vs. actual reason, what gave it away, ICP implication, and one specific fix.
4. For 3+ deals: you'll also get a cross-deal pattern table, one sentence naming the systemic issue, and one specific fix that changes what happens across the pipeline.
5. The ICP implication is often the most valuable output — if a buyer type keeps appearing in loss column, the AI will name it and say "stop selling to them" clearly.
6. Use "win/loss interview questions" mode to get 12 post-deal interview questions for buyer debriefs, with what each answer reveals about your process.

From a pattern analysis across 8 lost deals (B2B SaaS pipeline tool, $8K–$45K ACV):

PATTERN TABLE:
| Deal | Stage Lost | Buyer Profile | Stated Reason | Actual Reason |
|------|-----------|--------------|--------------|--------------|
| A | Post-demo | Solo founder | Budget | Never had budget authority — needed board approval |
| C | Post-proposal | 3-person startup | Timing | Evaluated too early, not in buying mode |
| F | Late stage | 8-person team | Competitor | Security review surfaced integration gap |

THE PATTERN:
You lose consistently when the economic buyer isn't in the room before the demo. Deals A, C, D, and G all had a champion who couldn't approve the purchase — and none were qualified out before two discovery calls were invested.

THE FIX:
Add one question to Stage 1 discovery: "Who else needs to be involved in a decision like this, and can we get them on our next call?" If they can't name a decision-maker or won't commit to involving them, stall the deal rather than advancing it. This would have filtered 4 of the 8 lost deals at Stage 1 instead of Stage 3.