Win/Loss Interview Guide

A sales leader or PMM who needs to run win/loss interviews that actually surface why deals close or die — not the polite fiction buyers tell in surveys.

- Interviewer briefing: setup, framing, and the one rule that breaks or builds credibility

- 12–18 core questions organized by decision stage: trigger, criteria, competitive, decision, reflection

- Probe prompts: 2–3 follow-ups per section to push past surface answers

- Win vs. loss question variants so you're not asking losers why they picked you

- Quick-reference one-pager with six highest-leverage questions for short calls

- 5–7 tagging frameworks for coding responses across 20+ interviews

- Explicit callouts for interviewer mistakes that shut buyers down

- Conversational, neutral language — designed to sound human, not corporate

Paste the prompt into ChatGPT, Claude, or any AI model. Answer five questions about your sales motion, deal cycle, competitor landscape, current win/loss assumptions, and where you want findings to land. Get a 1,000–1,400 word interview guide ready to deploy.

Bundles or prompts related to customer research and competitive intelligence.