Win-loss interview
Sales reps explain losses with 'price' and wins with 'great demo'. Buyers tell a different story. This template asks won and lost prospects about what actually happened — the trigger, the shortlist, the real deciding factor.
Best for: Founders, sales, and PMMs running win-loss analysis on recent deals.
Use this template free1 of 8
What was going on that made you start looking for a solution in the first place?
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The questions
- 1What was going on that made you start looking for a solution in the first place?Long textThe trigger event — reveals the job-to-be-done that opened the budget.
- 2Who else did you seriously evaluate before deciding?Long textNames your real competitive set, which is rarely who sales assumes.
- 3Walk me through how you narrowed it down — what got cut, and why?Long textPast-behavior framing surfaces the disqualifiers that never show up in a CRM.
- 4What was the single factor that decided it in the end?Long textForces one answer instead of a tidy list — the real reason usually surprises you.
- 5How did you make the final call?Single selectChose us / Chose a competitor / Built it ourselves / Did nothing — segment every other answer by this.
- 6Where in the process did you feel most confident, and where most uncertain?Long textMaps the moments your sales motion either earns or loses trust.
- 7Knowing what you know now, would you make the same decision?Single selectDefinitely / Probably / Probably not — buyer's remorse on a win is an early churn signal.
- 8What's one thing we could have done that would have changed your decision?Long text
How to run it well
- Run the interview within two weeks of the decision — the reasoning is sharp before people rationalize it into a clean story.
- Interview lost deals too, and weight them heavily; wins flatter you, losses teach you.
- Have a neutral party (not the deal's rep) ask the questions — people soften feedback when the seller is listening.
- Always ask who else they evaluated; the named competitor is often nobody your team was tracking.
- Tag every response by outcome and deal size, then read the 'deciding factor' answers verbatim — patterns there reshape positioning faster than any internal debate.
FAQ
Why interview lost deals instead of just won ones?
Wins tend to confirm what you already believe, while losses expose the gaps — the missing feature, the trust wobble, the competitor you underestimated. A balanced win-loss program needs both, and the losses usually move the roadmap more.
How many win-loss interviews should I run?
The same reasons usually start repeating after 10–15 interviews per outcome — won and lost separately. Run them continuously rather than in one batch so you catch shifts in why deals turn before they become a trend.
Can win-loss work as an async form instead of a live call?
Yes — a written form removes interviewer bias and scales to more deals, and buyers are often more candid in writing than facing the rep. Enform's branching keeps it conversational so the answers stay specific instead of one-liners.
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