Five Simple Strategies to Get the Most from Your Win-Loss Interviews

As we’ve discussed in previous blog posts such as this one, information gathered by interviewing buyers is key to gaining the best possible understanding of why sales opportunities are won or lost.

At Clozd, we've found that a large number of buyers are willing to provide feedback about their buying experience; but, asking potential interviewees for 30 minutes of their time is significant. Thus, it's important that you make the very most of each interview to ensure that the time spent is valuable for both the buyer and the consultant. Interviewees don’t want to feel like they’ve wasted their time, and the researcher wants insightful and comprehensive feedback.

No two interviews are exactly alike; but, in our experience we’ve found several strategies that, when put into practice, will help you get the most out of each interview:

Strategy 1: Do Your Homework


For consultants who’ll be conducting interviews on behalf of clients, it is important that they spend time learning about their clients’ product offerings, sales organizations, pricing structures, etc. If you'll be conducting interviews on behalf of your own company, then much of this foundation may already be in place. A solid foundation of knowledge about the business enables the interviewer to probe more deeply, anticipate the types of responses they may frequently hear, and adjust conversations appropriately.

It is also helpful, to the extent possible, to do some homework about the interviewee before the interview begins. Taking time to learn about the interviewee’s company, industry, and role will help the conversation run more smoothly. Having a basic understanding of where the product in question might fit into their organization can help you select relevant questions and frame them in the right way.

Strategy 2: Develop an Interview Guide


Doing your homework also involves preparing an interview guide that will act as a reference throughout the interview. For the sports journalist who plans to interview the high school quarterback, an interview guide may take the form of a few bullet points on a sticky note. For a win-loss interview, you’ll want to be more thorough - particularly because most B2B buying scenarios are highly complex.

The interview guide should be thorough enough to ensure coverage of critical topics, but with the understanding that a good consultant will still adapt on the fly. At Clozd, we work with each client to develop a custom interview guide. They are designed to address all the critical topics, while still leaving room for the interviewee to tell their own story. Our interview guides contain high-level, essential questions with optional sub-questions that help the interviewer probe about sub-topics that may surface during the interview.

Strategy 3: Be organized.

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A consistent, organized approach to interviewing can provide a better experience for the interviewee and improve data quality. For example, a great interviewer is respectful of the interviewee’s time by setting the right expectation about the duration of the interview and then sticking to it. In our experience, planning 30 minutes for each interview is a good goal. It gives the interviewer adequate time to cover essential topics, while not being too demanding on the interviewee. And, although 30 minutes may sound like a long time, it passes surprisingly fast once the conversation gets going.

Being organized also encompasses the technology you use (make it easy for the interviewee to sign up and participate) and the follow-up process (like automating a thank you message and gift card reward, as applicable). Having a reliable process will help you to improve participation rates and to avoid wasting precious time on technical delays or difficulties.

Strategy 4: Be Flexible


Again, no two interviews are exactly alike. Even buyers of the same product will have unique perspectives, priorities, use cases, budget constraints, decision processes, and so on. More importantly, the goal of any qualitative interview is to let the interviewee tell his or her story, in their own words. For these reasons, each interview will be unique and a skilled interviewer will be prepared - and able - to adapt accordingly.

At Clozd, we encourage and train our consultants to pursue the answer to the ultimate question of, “Why did you make the decision that you made?” That often requires us to "go off script" or flex beyond the standard questions of the interview guide. When interviewees give short, unclear, or unexpected answers, a skilled interviewer will skillfully adapt and tactfully probe to get to the heart of that key question.

Strategy 5: Summarize & Analyze Immediately


Just as important as the quality of your interviews, is the effectiveness of your strategy for tracking themes and trends across interviews. Take time, immediately after you complete each interview, to summarize high-level takeaways and identify major themes. If you record and transcribe each interview, you will have additional opportunities later on to review and refine those takeaways.

Writing a summary and conducting the analysis immediately after the interview will improve the accuracy of your analysis. Ultimately, an accurate analysis of the question "Why did they make the decision that they made?" for each interview is fundamental to the success of the program. Then, over time you can track themes and takeaways across interviews, looking for patterns and trends that might be meaningful for your business. 

As our founder, Andrew Peterson, describes, “Interviews are the essential foundation of any meaningful win-loss program. That's the reason your web search for win-loss analysis almost exclusively returns results related to win-loss interviewing.”

Following these strategies will help you make each individual interview a success and ensure the overall success of your program.

For more information about Clozd's win-loss interviewing services, visit Or, check out some of the additional resources below to learn about other critical win-loss best practices:

Win-Loss Analysis: Sample Size Considerations

Best Practice: Widespread Sharing of Win-Loss Data

Four Pillars of Effective Win-Loss Analysis