12 Tips for Better DIY Win/Loss Interviews

An ongoing win/loss interview program reveals systematic trends and identifies opportunities to improve win rates. However, these outcomes are much more likely if the interviews are conducted and analyzed with a structured approach. This is a key benefit of using an external market research firm. But, if you are tasked to conduct win/loss interviews for your company, the following tips will help you get the most out of it.

These tips will help you ask the right questions, set up calls with those elusive lost deals, conduct a better interview, and produce an objective analysis.


Many factors influence the outcome of a deal. Using a framework of questions ensures that your interview captures the full story and you understand the context for the decision.  

Topics to Explore: There are six key dimensions that most firms (including Isurus) consider best practice to include in a win/loss interview.

  • Purchase motivation: What prompted the evaluation of vendors? What the prospect was hoping to accomplish?
  • Purchase process: How were vendors identified? What information sources were used?
  • Decision team: Who was involved in the process and what were their roles? Who was the initial champion? Who made the final decision?
  • Decision criteria: What were the primary they criteria used to compare vendors? Product attributes (features, ease of use, etc.)? Vendor attributes (expertise, size, brand reputation, etc.)? Cost (upfront, ongoing, etc.)?
  • Key differentiation: What did they see as your strengths? What did they see as competitor strengths?
  • Sales interactions: How did your firm compare to competitors on discovery process, clear proposal, responsiveness, knowledge of prospects company, etc.

The emphasis of each dimension can be adjusted to fit your product or market, or your hypotheses about potential problems.  For example, if your team thinks the sales process isn’t well aligned with the customer decision process, you may weight your questions to dig more deeply into the decision team and sales interactions.

As you build your questions in this framework, start with an existing template. There are useful win/loss question templates available from the Product Marketing Alliance and the Pragmatic Institute.

Knowing the right questions to ask is only half the equation. You still need to schedule the interviews, pull out as many insights as possible during the call, and then extract overall trends from all the interviews.


Before you can put your questionnaire and framework to use, you must schedule the interviews. Wins are always easier to schedule, for a range of reasons. Their contact information in your CRM is typically correct. They feel more vested in the success of your product and company. As a new customer they have more enthusiasm and willingness to participate in interviews. The challenge is connecting with losses.

Incentives: Losses chose another direction and have little motivation to spend more time with your company. In addition to emphasizing that you sincerely value their feedback, another lever is to offer a gift card or charitable donation for participation in the interview. The amount varies by segment and organizational level. An incentive of $100 may be enough, or it may require $300 if your target interviewee is more senior, or your working with a very small list of contacts.

Allocate Time: Plan on spending a few hours trying to connect with each loss on your contact list. And expect more than a few dead ends. You can expect about a 10% acceptance rate from losses: For every 10 people you contact, 1 will agree to the interview. Your emails get lost in their cluttered inbox. Voicemails and gatekeepers make it hard to connect. They have busy schedules. But persevere and you will schedule the interview!


After the interviews are scheduled, the next challenge is to squeeze as many useful insights as you can from the interview. The following are some techniques that can improve your interviewing.

Tell Me More: People often give short of vague answers. Simply following up their responses with variations of “Tell me more” leads people to give a more detailed answer. Be sure to pause to give people time to finish their thought.

Laddering: In win/loss interviews, people is first answer tends to be the “what” and not the “why”: Ontime delivery was an important factor in our decision. The technique of laddering helps uncover underlying needs/barriers through a series of probing follow-up questions: Why is on-time delivery important? Followed by “Why is that important?” “What happens if a shipment is delayed?” “Tell me more about that.”

What’s not said: Often what is not said provides as much insight as what is said. This is especially useful when evaluating existing hypotheses. For example, you may have assumptions about barriers that keep customer from selecting your product or service. But if those assumptions don’t arise spontaneously as a reason your product was not selected, they are likely less of a barrier than you expect.

Listen, Don’t Explain: The objective of the interview is to listen to the customer. It sounds simple, but it is easier said than done. You may find yourself wanting to address objections – to sell customers on the idea or defend your company’s actions. Resist this temptation. It does not help win a loss back and may inhibit candid feedback. Attentive listening will also help you uncover the personal or emotional drivers behind a decision.

Repeat the Big Idea Back: People may give long, convoluted answers to your questions and wander off on tangents. If this happens, summarize what you heard before moving on. “So, you are saying,” “Did I hear you right?” keeps the conversation focused and makes sure you understand the respondent’s main point. This technique also helps ensure your bias as an insider doesn’t lead to accidental misinterpretation.

Set Expectations Upfront: Setting upfront expectations for how much needs to be covered in the interview helps manage individuals that are prone to go off on tangents. Use this statement when you start the call to lay the groundwork for pulling an interviewee back to the topic when they go of the rails: “We have a lot to cover today and I want to be respectful of your time. If I move us along its only to ensure we cover everything in the time you shared with us. I’m happy to go longer if you can.”


Your interviewee isn’t the only one that needs managing. You need to manage yourself to ensure you conduct the interviews systematically, capture all the information, and set yourself up to analyze the trends across interviews. It’s easier than you might expect to become focused on the most articulate interview, or your most recent one, and forget the larger trends running throughout your interviews.  

Follow the Guide: You’ll use the framework to create a set of questions—called the interview guide—to conduct your interviews. The guide’s structure plays an important role in the analysis and should generally be followed in each interview. This may require coaxing an interviewee back to the topic at hand and telling them that some subjects will be discussed later in the conversation. It also provides a roadmap to keep you on track as well. While each deal and individual will have unique characteristics to explore, your goal is to identify systematic trends that impact the overall win rate. If you ask different questions in each interview, you end up with a collection of anecdotes rather than a cohesive data set.

Record the call: Each in-depth interview collects a significant amount of data – too much to realistically be captured by an interviewer taking notes. Recording the conversation addresses this problem and provides additional benefits. It allows the interviewer to focus on the conversation – rather than taking notes. The conversation can be transcribed and used for a robust analysis and quotes for reports. Remember to ask your interviewee permission to record the call, and explain how the recording will be used.

Keep a Spreadsheet Summary: Immediately logging highlights from each interview into a spreadsheet helps facilitate the data analysis process and can provide quick top-line findings when needed. The spreadsheet also helps address three common challenges.

  • Giving more attention in the analysis to the more articulate participants – They are easier to interview and they stand out more in your memory, but their data aren’t more valuable than other participants.
  • Recency bias – The feedback from the most recent interview overpowers your recall of the feedback from the first interviews.
  • Sporadic interviewing – Your interviews will be scattered across your calendar and sandwiched between other meetings and obligations. Quickly reviewing the spreadsheet before your next interview refreshes the topics and gets you in the right mind-set.


With the right question framework, effective interviewing techniques, and systematic data capture, your win/loss interviews can produce meaningful insights that positively impact your win rates. Many B2B marketers manage all these activities internally. Others find they need assistance and turn to outside research firms. If you’d like to explore how Isurus may be able you help you can reach us here.