How To Run Great Win Loss Interviews

How To Run Great Win Loss Interviews

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Adam Ramshaw
Adam Ramshaw has been helping companies to improve their Net Promoter® and Customer Feedback systems for more than 15 years. He is on a mission to stamp out ineffective processes and bad surveys.
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Losing a big B2B opportunity is more than disappointing – it’s also expensive. Typically the process has taken a long time to complete: maybe even a year or two. You will have invested substantial staff time, travel and other expenses.

To salvage something from all that investment you should run win loss interviews for key projects to help you continuously improve your sales process.

In this post I outline exactly how to conduct a win loss interview that will help you understand where you went right and wrong so you can fix it next time.

For a list of won loss analysis questions you should ask – chin the interview check out this post: 13 Must Have Win Loss Analysis Interview Questions.

What is a win loss interview?

A win loss interview is when you interview staff at organisations where you have recently won or lost an order. The goal is to learn what you did well and what you need to improve, so you can perform better in future sales opportunities.

When Should Win Loss interviews be Performed?

You should perform the win loss interview as soon as possible after being informed by the customer of the win or loss. Sometimes customers will delay the interview until after the contract with the winning vendor has been signed.

How to Conduct the Win Loss Interview

Do an Interview not a Survey

Email surveys are much lower cost than telephone or in-person interviews but they are not effective for win loss analysis. So even though they are low cost, they are a waste of money.

Customers responding to on-line surveys spend little time thinking about their answers and, in generally, are just trying to get them completed.  

Pre-formatted surveys also don’t allow you to drill into interesting responses with effective followup questions.

Win Loss Interviews are more expensive but they are also worth every cent.

Have a Third Party Do The Interview

Use an external firm to conduct your win loss interviews. This is important for several reasons:

  1. Customer honesty: Customers are more likely to be honest when they are not talking to someone directly involved in the sales process. 
  2. Staff defensiveness: Staff involved in the loss are also more likely to become defensive if they hear negative comments. Often they will try to rebut the interviewee’s points. The time for overcoming objections is gone – this is about correcting course for the next sale
  3. Fresh insights: A third person comes to the interview with fewer assumptions and preconceived ideas of why the sale was lost so will be more open to clearly hearing what the customer is saying.

If you can’t use an external company, the win loss interview should at least be done by someone not directly related to the project, e.g. marketing, a different sales person, manager, etc.

Don’t ask Too Many Questions

Don’t pepper the respondent with dozens of questions. Instead, ask a few broad questions and then drill into the responses by asking clarifying questions.

Ask Open Questions Not Yes/No questions

Asking Open questions encourages the respondent to provide additional, context around their answer: what were there considerations, how did they perceive the process, etc. This content is critical for the analysis phase of the process.

Conversely Closed (Yes/No) questions shut off the conversation and provide very little information about the context. You end up having to ask “why” to understand the context anyway.

Consider how these two questions shape the response:

(Closed): Did you find our proposal effective?

(Open): What did you think of our proposal?

Record and Transcribe the Interview

Collecting the exact wording of what is said in the win loss interview is very important during the analysis stage. 

Instead of trying to write notes, record the interview and have it transcribed later.

This allows you to concentrate on the answers and ask probing followup questions while also being certain of getting the exact terminology used.

Modern tools make this process simple and low cost.

Zoom, Google Meet and Microsoft Teams all allow you to record a video call. You can then upload it to a variety of AI and human based transcription services.

Make sure you get permission from the respondent to record the interview.

Offer to Make the Interview Confidential 

If the respondent knows their name will not appear beside their comments in the final win loss analysis they are more likely to be open and honest in their feedback.

Don’t Ask Questions Where You Already Know the Answers

Before the interview, collate everything you know about the customer so you can use it in the analysis. That way you don’t need to use the limited time a respondent gives you collecting data you already know.

For example you should collect data about: the industry the customer is in, their size, which “titles” were involved in the sales process on both the customer and company side, etc.

In the analysis phase compare and contrast the different customer responses with the other information you have.

Don’t Be Fooled By Price 

Very often customers will cite price as the reason that you lost or won a sale but it’s almost never the true underlying reason for losing business.

When they say “price” they are really saying:

The other parts of your offer were not good enough to justify your price in comparison to other vendors

If you hear “price”, you need to dig deeper to understand the real causes for the loss.

Explore areas around functionality, trust, experience, etc. to see if you can find the real reason your competitor walked away with the order.

Be Realistic in What They Will Tell You

If, for instance, you lose a government contract that was predicated on accepting the lowest price, the respondent will be required to respond “price” as the reason you lost.

There will also be a level of confidentiality in the information other suppliers provided in the sale process. Don’t expect customers to disclose this information to you.

Be prepared for this and select questions that can be answered effectively, so you don’t waste time and annoy the customer with unanswerable questions.

Build Rapport With Open Ended Questions.

Start your interview with a couple of easy, non confrontational, questions to build rapport. When the customer is more relaxed you can ask more probing questions.

For example don’t start with:

Can you tell me the main reasons we did not win this project


What did you think of our pre-sales process

Don’t Answer You Own Questions

Always ask questions in a neutral, non-accusatory way that does assume a particular answer. You don’t want to pre-dispose the respondent to answer any particular way.

For example, iinstead of

 Tell me why you didn’t like about our software interface


Tell me about our software interface

The first question almost requires the respondent to find faults even if they didn’t notice any. The second version gets their top of mind, most important, views on the subject .

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