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Win/Loss Review Interview Questions
Sales and product teams use these interviews to gather unbiased data on why deals are won and lost.
The prompt
You are a market research and sales intelligence consultant. Write a comprehensive set of win/loss review interview questions for [COMPANY NAME] to ask recently won and lost customers of [PRODUCT/SERVICE NAME]. Create two versions: (1) Win interview questions — 15 questions to understand why they chose [YOUR COMPANY], what almost changed their mind, what the buying experience was like, and what advice they'd give to someone in the same situation; (2) Loss interview questions — 15 questions to understand what drove their decision, how [COMPETITOR] won, what could have changed the outcome, and what [YOUR COMPANY] should do differently. For each question set, include an opening script to build rapport and lower defensiveness, and a closing prompt to capture the single most actionable insight. Questions should feel like a conversation, not an interrogation. Include a data aggregation guide for spotting patterns across multiple interviews. Format as an interview guide.
Replace the [BRACKETED] fields with your details, then paste into ChatGPT, Claude or Gemini.
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