The Best Way to Do Your Win/Loss Customer Interviews in 2025

Regardless of whether you are working through your first sales or already gained traction on the market, you need a continuous improvement process that helps you improve your sales strategy. This is one of the critical factors behind successful businesses - increasing their learning rate. Thriving companies embrace every opportunity to complement their understanding of their customers’ problems and needs.

Conducting a win/loss analysis is an excellent opportunity to increase your learning rate by identifying trends and blind spots in your sales process. By the end of this article, you know what is the best way to improve your sales cycles by gathering win/loss data.

What are Win/Loss Interviews?

A win-loss interview happens after your interaction with a potential customer is completed, regardless of whether it was successful (win) or not (loss). The goal of the interview is to capture key moments from the sales process and extract insights about improving the win rate.

This type of interview is a powerful way to understand your customer's complete experience with your brand and, most importantly, what influenced their buying decision.

Why are Win/Loss Interviews Important?

This question has two sides - why are the interviews with lost customers important, and why are the interviews with won customers important?

Based on the feedback from lost deals, your goal is to improve your sales tactic so you can increase your win rate. Potential insights that such interviews can uncover are:

• Mismatches between initial product positioning and what was discovered during the interview
• Deal breakers
• Important stakeholders in the decision-making process who can veto your deal and their interests
• Existing alternatives to your product and how

The interviews with customers who decided to continue with your product can inform you of:

• Stakeholders that champion your product
• Your unfair advantages and unique value proposition or, in other words - where your product excels ahead of the competition
• How to retain your customers through understanding what value they expect from it

Interview Preparation

When executed correctly, interviews can yield invaluable insights. However, an interview is much more than a “casual conversation” with your prospect. Professional researchers follow a well-developed methodology that ensures interviews are conducted confidently. Here are the key steps for effective win/loss research in a nutshell.

1. Define Clear Objectives

The objective is the purpose of your research. For a meaningful objective, it needs to lead to improvement in your sales, marketing, or product management strategy.

2. Select the Right Participants

The power of the Win/Loss interviews is that they include a diverse range of customers and provide a holistic overview of your brand experience. Make sure you include representatives of all customer segments that you target with a wide range of demographics.

Timeliness is an essential factor for efficient interviews - make sure to talk with people who interacted with your company no later than the last three months, ideally up to a month. Beyond this period, it will be harder to extract and capture important nuances and emotions from the interviewee's situation.

3. Prepare interview script

The difference between a casual conversation and a well-conducted interview is having an interview script to follow. An interview script ensures that the conversation covers all topics of interest and is conducted in relatively the same context. This ensures that responses can be aggregated and compared across different interviews.

Having a prepared set of questions also ensures that the questions you ask are well-defined and will not mislead or guide respondents to specific answers. Preparing a well-thought-out interview script is a separate topic on its own. If you are interested in that, skip to the last paragraph of this article.

4. Set Up the Scene

The interviewee is dedicating part of their precious time to share their experience with you. Make sure they know you appreciate that and their opinion is valued.

Create a scheduling process that works for your respondents. Giving them the option to pick the time and place (including online) to have the conversation will significantly improve your response rate.

5. During the Interview

Remain neutral, record (after taking permission), and take notes. Your goal during the interview is to extract as much information as possible - you are not here to revert their decision if they decide not to buy your product. Also, make sure you are not starting a debate and trying to prove them wrong for anything. Their point of view is theirs, and your job is to understand it as deeply as possible.

In other words, try to stick to your interview script as much as possible.

6. Analyze and Synthesize Insights

Once you have conducted several interviews, you will start seeing patterns. These are the insights you are looking for from your research that needs to be aggregated and summarized.

The Icanpreneur Way for Win/Loss Interviews

From everything above, conducting customer interviews according to the best practices may feel overwhelming. There are A LOT of things to consider, and many of these steps require experience and practice to be mastered.

That’s why Icanpreneur is on a mission to ease this process for you and handle the most complex or mundane tasks. Here is how Icanpreneur can help you do a Win/Loss analysis

1. Prepare a custom-tailored Win/Loss Script Interview for Your Business

The Icanpreneur Virtual Assistant (IVA) will prepare a customized list of win-loss interview questions based on everything she knows about your product and the customer segment you will be interviewing. Needless to say, the script is generated according to the industry standards for product research and minimizes misleading or biased questions.

The questions are divided into sections that cover all the insights you need to extract. Each section has guidelines for the time you should spend on that part of the conversation so you don’t miss anything.

You can expand or change the script in collaboration with your teammates if necessary. (Yes, Icanpreneur is a multiplayer game!).

When ready, you can print the document on paper and bring it with you or export it as a PDF and read it from your screen.

2. Analyze and Extract Insights

Analyzing tens or even hundreds of conversations can be a tedious task. IVA can do that in minutes for you, giving you repeating themes across the whole set of interviews. You can deep dive into each specific insight and the interviews that contributed to it, get quotes from the interviewee that support the insights, and so on. If you have some ad-hoc questions - you can always ask IVA about them, and she will respond with the knowledge she gathered from the interviews.

3. Continuous Improvement

IVA can also give you insights into what you can do better in your next interview to maximize what you learn from each conversation. Think of it as your personal coach who is always with you during the interviews and gives you actionable insights after them.