Win-loss interviews are one of the most powerful tools for understanding what really drives your customers' decisions—and let’s be honest, it’s rarely as straightforward as we’d like to think.
Was your product lacking critical features? Was it really too expensive for the buyer? It takes a real conversation to know for sure.
When you regularly interview your buyers, including those who went with a competitor, you get a stream of extremely relevant insights for your Product, Sales, and Marketing teams.
The good news is that those interviews are easy to implement… if you can avoid some common traps!
In this guide, we’ll teach you how to get them right, and we’ll share the big secret to great Win-loss interviews. Let’s dive in!
20 to 30 minutes is the sweet spot you should aim for. Interviews shorter than that won´t give you the time to dive deep into the reasons for the buyer’s decision.
Indeed, B2B sales cycles are getting more and more complex. It’s almost always better to do in-depth interviews with few buyers, than surface interviews with 100% of them.
Moreover, the longer and more complex your product and your sales process, the longer should be the win-loss interviews. The decision process for a complex, 5-figures contract can’t be glossed over in 10 minutes.
The person running the interview plays a huge role in how comfortable and honest the buyer feels, which has a lot on influence on the quality of the feedbacks.
Here’s a breakdown of your options:
Don’t go into the interview armed with 50 questions. Instead, make a list of 5-8 data points you need to gather, and let the conversation flow naturally around them.
Your checklist might look like this:
Having these focus points ensures you don’t miss anything important and lets you know when the interview is complete.
Here’s the truth about win-loss interviews: they’re not about you. They’re not about your product, your sales process, or even your burning curiosity to know why you didn’t close that deal. They’re about your buyer. You must let them tell their story.
A common mistake in win-loss interviews is treating them like a checklist. If you’re rigidly working through a script, you’ll miss the chance to uncover deeper truths. And yet, that’s how many interviews are done today, even by experienced user researchers.
Here’s a scenario you want to avoid: You hop on the call, rush through a list of questions—“Who did you choose? Why? What didn’t you like about us?”—and before you know it, the call’s over. What did you learn? Not much.
Instead, think of yourself as a guide, not an investigator. Ask a thoughtful opening question, and then let them speak, ask them to clarify key points, and prompt them to share more. The best interviews happen when the buyer is doing 90% of the talking.
Sitting quietly while someone talks might feel like you’re not doing enough. But active listening is the ultimate skill for a win-loss interview. When you’re listening, you’re not just hearing words; you’re picking up on tone, hesitations, and underlying motivations. And when buyers feel heard, they open up even more.
Avoid the trap of asking the questions backwards from the present situation: “Why did you choose X? Ok. What other options did you consider? What was important?” .
This forces the buyer to retroactively justify their decision and puts them in a defensive mode.
Instead, invite them to narrate their journey from the beginning. This helps you follow the natural flow of the buyer's decision-making process—starting from the problem they faced and leading to the solution they chose.
Those open-ended questions will help you keep the conversation moving forward along your buyer's journey.
Help the buyer articulate the challenge they faced. These questions should focus on their specific situation and needs:
Encourage them to share how they approached finding solutions and what sources they trusted:
Find out what mattered most to them as they compared options and weighed the pros and cons:
Uncover what ultimately influenced their choice and how they perceived your product versus the competition:
Before you dive into your next meeting or check your email, take a moment to document the interview. Yes, even if you recorded it.
If you followed the advice and let the buyer tell their story, the hard part is already done. You’ve uncovered the “why” behind their decision, their priorities, and maybe even some frustrations.
Buyers often say things that are clearer than any slide deck ever could. While quantitative data should remain the basis of your analysis, adding quotes brings authenticity to your findings and will make people remember them.
Start by adding key data points directly into your CRM, product management software, or other tools your teams use daily.
Your tool should make it easy to capture the following structured data
Having structured data is important to compute metrics such as the number of deals lost by reason, and generate win-loss dashboards that track trends over time.
Win-loss interviews take effort—setting them up, preparing, conducting, and analyzing. But all that effort is wasted if you cut corners when it matters most.
Buyers don’t want to feel interrogated—they want to feel heard. When you actively listen, show genuine curiosity, and let their experience guide the conversation, you’ll unlock the kind of insights surveys simply can’t provide.
So go ahead, dive in, and make these interviews count—you’ll be glad you did !
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