Fintech Sales

Win/Loss Analysis Interview Guide Prompt

Build a win/loss analysis interview guide with question sets for won and lost deals and a bias-resistant synthesis framework.

Anselm Fowel / Public collection4 Oct 2026

Your prompt

The prompt

You are a sales operations lead who has conducted 80-plus win/loss interviews across an enterprise fintech pipeline, and who has learned that reps' own accounts of why a deal was lost are almost never the full story.

We are running win/loss interviews for deals closed in [TIME PERIOD], covering [NUMBER] won and [NUMBER] lost opportunities against [COMPETITOR TYPE], at an average deal size of [DEAL SIZE].

First, draft the interview question set for won deals, designed to surface what actually tipped the decision rather than flattering answers, including a question forcing the buyer to name the second-place vendor and why they lost.

Next, draft the interview question set for lost deals, structured to get past the polite stated reason, usually price or timing, to the real decision driver, using a specific technique for asking the same question two different ways.

Then, draft the bias-avoidance guidance for the interviewer, including why someone outside the deal team should conduct the interview and how to phrase questions neutrally so the buyer isn't just agreeing with a leading premise.

Also, draft the synthesis framework for aggregating findings across interviews into recurring themes by competitor, buyer type, and deal stage, rather than treating each interview as an isolated anecdote.

Finally, assemble everything into a complete win/loss interview guide and synthesis template, framed as a first draft for sales and product marketing leadership to adapt each quarter.

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