---
title: What questions should you ask in a win/loss interview?
canonical: "https://winlossresearch.com/faq/what-questions-should-you-ask-in-a-win-loss-interview/"
description: "A win/loss interview should ask about the buying process, evaluation criteria, competitive comparisons, and specific objections."
---

# What questions should you ask in a win/loss interview?

A win/loss interview should ask about the buying process and internal decision discussions, the evaluation criteria the buyer used, competitive comparisons, pricing perceptions, whether messaging resonated, and the specific objections that shaped the outcome, opening broad before narrowing into specific topics like price or competitors.

## Start With the Buying Process, Not the Outcome

The most productive opening question in a win/loss interview is broad: something like "walk me through how the decision got made." Asking a buyer to narrate the process, rather than jumping straight to "why didn't you choose us," gives them room to volunteer the internal committee dynamic, the stakeholder who raised a late objection, or the moment a competitor made a stronger impression, details that a narrower opening question would never surface.

## The Core Topics an Interview Should Cover

Beyond the opening, a well-built [interview questionnaire](/glossary/interview-questionnaire/) moves through evaluation criteria (what the buyer actually used to judge the options, which often differs from what the vendor assumed mattered), competitive comparisons (which vendors were considered and how they stacked up), pricing perception (whether the pricing structure was clear and felt fair, independent of whether it was ultimately a dealbreaker), messaging resonance (whether the vendor's positioning actually landed as intended), and the specific objection or concern that proved decisive.

## Why Question Order Changes the Answer

Asking about price early in the conversation primes buyers to treat it as the central factor, even when the underlying decision had more to do with something else entirely. Sequencing broad, open-ended questions before narrow, specific ones is what keeps a questionnaire from accidentally confirming its own assumptions rather than surfacing what actually happened.

## What to Leave Room For

The strongest findings in a win/loss interview often come from a follow-up question that wasn't on the original list, asked because a buyer mentioned something unprompted worth exploring further. A fixed script, read verbatim without room to follow an unexpected thread, tends to produce interviews that are efficient but shallow. Building in that flexibility is part of what separates a useful [win/loss interview](/glossary/win-loss-interview/) from a rigid survey administered out loud.

## Adjusting Questions to the Specific Engagement

The exact questions worth prioritizing shift depending on what a program is trying to learn. An engagement scoped around understanding a recent drop in win rate against a specific competitor should weight competitive comparison questions more heavily than a generic template would. An engagement focused on testing whether a new pricing model is landing should spend disproportionate time on pricing perception, even if that means a shorter competitive section. Building the [interview questionnaire](/glossary/interview-questionnaire/) around the client's specific GTM questions, rather than treating every topic as equally important in every engagement, is what makes a thirty-to-forty-five-minute conversation actually productive.

## Related

- [Win/Loss Research Methodology](/topics/win-loss-research-methodology/)
- [How do you design a win/loss interview questionnaire?](/faq/how-do-you-design-a-win-loss-interview-questionnaire/)
- [What questions does win/loss research answer?](/faq/what-questions-win-loss-research-answers/)
- [Interview questionnaire](/glossary/interview-questionnaire/)