45 Powerful Win-Loss Questions to Ask Your Customers

Posted on: April 12, 2023
By: Matthew Reeves

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We — modern businesses — gather every analytic imaginable. Every software has a reporting section.

But, they miss one measure: customers’ actual perception – in their own voice.

That’s what win-loss does: its pure voice-of-the-customer research.

In this post, we’ve compiled a list of great questions to include in your win-loss survey. Use it for inspiration if you are lost about what to ask. 

How to use these questions

This list of questions is designed to be used in win-loss analysis interviews with both customers who’ve purchased your product and those who did not. Some quick tips: 

  • Choose and adapt which questions you feel are most relevant.
  • Keep interviews to 30 minutes or under. 
  • Talk to people who were in your most recent sales cycle so their memory is fresh
  • Record buyer interviews — it’s easy to parse the data into a win loss report. 
  • These questions are a guideline, not a script. Always ask follow-up questions like “could you tell me more about that” to dig into the details of your interviewee’s experience. 

Table of Contents

2 Questions understand why the buyer reached out to you

“When you got a [demo/signup/talked to] [product], what led to that?”

“Why was now the right time to reach out?”

2 Questions to understand how buyers think about the problem

“What does [product] do for you or your team?”

“Why was now the right time to look at [product]?

2 Questions to gather market intelligence

“If you were told you  couldn’t buy a new technology, how’d you solve this problem?”

  • This helps gather a picture of non-technology alternatives.

“If you couldn’t use [product] for whatever reason, what would you do?”

  • Whereas this question uncovers similar software tools.

3 Questions that uncover first impressions

“Think back to when you first [saw / tried] [product], what stood out to you?” 

“Was it as you expected it to be?”

“Is there a feature of [product name] that you think is underrated? If so, why?”

3 Questions to understand perception of your product

“How would you describe how [product] works to your coworker”

“How woud you describe [product] to [grandparent/CFO/friend outside of tech/somebody who knows nothing about it]”

11 Questions to gather competitive intelligence

“If you were describing the top three options for you: what are they, and what are the pros and cons of each.”

“If you couldn’t use [product], what would you do?”

“If you couldn’t use any of its competitors, what would you do?”

“Did you research multiple companies when looking for a solution to [customer’s pain point]?”

“How did you make your shortlist of companies?”

“Do you look for news and thought leadership on [industry] on any tool, platform, or outlet? 

“If you had to give me a 2-minute understanding of all the options and the pro’s and cons, what would you say?”

“What other options did you seriously consider? 

“What is the most similar to [product]?”

“What is the most different to [product]?”

“What led you to ultimately [choose/not choose] [product]?”

10 Questions to uncover buyer requirements

“At the beginning, what were you must-have requirements?”

“As you researched, did you discover things that became must haves?”

“Did any of the products have any neat functionality or traits that made them stand out?”

“If you had a magic wand, and you could tweak [product] to be perfect just for you – what would you change?”

“If [name], the CEO of [company] had a heart-to-heart with you and asked what should change, what would you say?”

“Before seeing a demo, did you have criteria that you were looking for?”

“And what was that criteria?”

“Did your criteria change over time? If so, what brought about that change?”

“Can you explain what led you to feel that [product] met your criteria?”

“I noticed that we didn’t meet [specific criteria mentioned by customer], how important was that in your decision to [choose us/not choose us].”

4 Questions that understand the buying experience

“What steps internally did you have to take to buy [product] from your side.”

“What steps did the vendor need you to go through.” 

“How was that process? What went well and what didn’t.”

“Were there any major differences in the sales process between different options” 

3 Questions that show what factors influence decision-makers

“Who was involved in researching solutions to resolve [customer’s pain].”

“Were there any other key stakeholders you or others needed to convince?” 

“Was there one particular person who had the final say? If so, what was your interaction with them.”

5 Questions to gather the win-loss reasons

3 for lost deals

“What were your primary reasons for choosing [competitor]?”

“When did you know that [product] wasn’t a good fit for you?”

“What would [product] have to change or do differently for you to have chosen them?”

2 for won deals

“What ultimately led you to [purchase/upgrade] [product]?”

“When did you and the team know that [product] was worth the investment?”

Additional information:

2 tips for asking better questions during customer research interviews

Asking someone a question and getting an answer is easy. You do it a million times a day. But interviews are different because they require active listening, empathy, open-ended questions, and the ability to probe deeper

You want interviewees to factually remember their actions’ reasons without putting a positive spin on them. Here’s how. 

Tip #1: Avoid the bias trap

Any question you ask can sway your customer into giving you a positive or negative response. Can you spot the bias in the two questions below?

How easy did you find using the software when you first signed up?”


“How did you find using the software when you first signed up?”

As you might have guessed, variation A will bias the interviewees’ answers. By assuming our customers found it “easy” to use the software, we’ve set off a chain of psychological responses. 

The subconscious mind thinks, “Ah, they want me to tell them what was easy,” and immediately scratches off all details that don’t fall into the ‘easy’ category. And suddenly, you’ve spent 30 minutes learning about one isolated aspect of your customer’s journey.

If your interview is to collect positive reviews, biased questions are great. But for a win-loss purpose, the answers are almost useless. 


You’re not holding these interviews to learn what’s right and wrong about your product. You’re holding them to learn what your customers think, feel, and do. 

Just being aware of biased questions reduces your chances of asking the wrong thing. 

Here are a few extra tricks you can use to reduce bias in your interviews to ensure you get the best quality feedback possible.

  • Write a question script so you can ask the right questions. 
  • Practice interviewing a colleague.
  • Have an “avoid bias” sticky note on your computer screen during interviews to remind yourself. 
  • Ask open-ended questions like “what led you to…” instead of “why did you…” 
  • Slow down when asking questions and formulate your answers methodically as you talk. 
  • Hire an external interview team to consult or train you and fellow interviewers

Most importantly, try to stay calm and collected — even experts find some interviews challenging. When you truly want to hear your customers’ opinions, the best and most impactful questions come naturally to you.

Tip #2: Remember, this conversation needs to uncover certain information.

When we talk to customers about interviews, we use phrases like “quick chat” and “honest opinion.” But the truth is that, as marketers, we always need a clear goal to validate our time spent.


Don’t know who the right people are to interview? If you have a large user base, consider running online surveys to pre-qualify people before you make a final decision and jump on a call with them. 

So think, why are you interviewing customers? What do you want to discover? 

Blocked on what new features to build? Guide conversations with high-value customers toward what’s currently blocking customers so you can ideate on solutions.

Notice acquisition is tapering off? Ask your best-fit customers about their pains, motivations, and desired outcomes so you can update your messaging. 

Stuck with a poor onboarding conversation rate? Ask brand new customers and trial users what it was like to get started so you know what works and what doesn’t. 

When you focus on the end goal of your interview, it’s easier to better understand what factors, thoughts, and impressions are pushing customers to buy or drop off. 

What is a win-loss analysis interview?

A win-loss interview is a quick 30-minute chat with a won customer or lost lead about their experience with your product. The conversation covers everything from their initial struggle and searches for a solution all the way through to why they did or didn’t purchase.

How can I use win-loss interviews to improve sales?

Win-loss interviews give you the data needed to make decisions for the following tasks or goals confidently:

  • Product development roadmap (What new features should we build?) 
  • Marketing messaging (How should we sell the features we have?) 
  • Positioning messaging (How can we memorably position ourselves against our competitors?) 
  • Sales messaging (What can sales teams say to convince customers to trust we can do what we say we do?) 
  • Demo messaging (What features should we prioritize during demos, and how can we simply describe them?) 
  • Support documentation (How can we better document our product to reduce misconceptions that lead to a high loss ratio?) 

So now you know what questions to ask

It’s time to jump on a conference call and listen to direct feedback from your customers. Do enough interviews, and you’ll know what factors influence your customer’s purchase decision. And that means you can make better, more relevant decisions. 

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