Article · 14 min read

How to Conduct Win-Loss Interviews: Step-By-Step Guide

Klue Free Beginner

The interviewing craft, not the theory: how to open so people feel safe being blunt, how to use five whys past the polite answer, and why you let the buyer talk ninety percent of the time.

  • Follow the 90/10 rule in a win-loss interview: the buyer should be speaking 90 percent of the time.
  • Plan for 30 minutes but block an hour, and prepare 20 to 30 questions knowing you will use 10 to 15.
  • Uses a D.E.P.T.H. structure (details, engaged, personal, trust, high impact) plus five-whys laddering to get past the first answer.
  • 41 percent of win-loss programs are now owned by product marketing (2025 Win-Loss Trend Report).
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It answers 2 questions

  1. Our CRM says we lose on price. I do not believe it. How do I find the real reason, and what does it say about who we should be selling to?
  2. Everyone has an opinion on our new messaging and nobody can settle the argument. How do I test it instead?

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