13 Must Have Win Loss Analysis Interview Questions

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Looking to run some win loss analysis interviews but you’re not sure what to ask. Keep reading – here are the only questions you need.

See our guide on how to run a great win loss analysis interview for the bigger picture on the process but remember your pre-prepared win loss analysis questionnaire is just a starting point. You’ll need to ask impromptu questions based on the responses you hear. 

However, in this post I cover what you should put in your win loss analysis questionnaire and what you should definitely not put in it.

Questions To Include In Your Win Loss Analysis Questionnaire

Questions About the Sales Experience

These are less confrontational questions and are great to use at the start of the process to help build some rapport with the interviewee. They look at how your sales team worked with the customer’s buying team.

  • What did you think of the overall sales experience?
  • What is your perspective on our proposal and documentation?
  • How well did we customise our presentation and/or deliverables to your business needs?

Understanding Product / Service / Software Competitiveness

Of course you should learn if what you’re selling doesn’t meet what the market wants.

Here are a couple of broad questions that will get the customer thinking about what they liked or didn’t like about your solution.

  • What did you like most about our product/service/software/offering?
  • What did you like least about our product/service/software/offering?

Win Loss Analysis Competitor Questions

This is always a tricky area and, depending on the governance that surrounds the buying process, the customer may or may not be able or willing to share details of your competitors.

You should ask these questions though – the customer will quickly let you know if they will not answer them:

  • How many other companies did you investigate in the buying process?
  • Who else did you consider in the buying process? (i.e who where your competitors)
  • What were our strengths vs the other companies in the process?
  • What were our weaknesses vs the other companies in the process?

The Critical Win Loss Analysis Questions

Towards the end of the interview, when you have hopefully established some rapport with the prospect, it’s time to ask the more confronting, but ultimately, most critical questions: why did we win/lose the order.

Here are four good win loss analysis questions to ask:

  • What do you think is the biggest difference between us and the competition?
  • What were the main reasons we were not successful in this sale?
  • What would be the most important areas for us to focus on to win your business in the future?
  • Do you have any other feedback for us?

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

So, if you hear “price”, you need to ask more questions to understand the real causes for the loss.

Ask some off the cuff questions to explore areas around functionality, trust, experience, etc. to see if you can find the real reason your competitor walked away with the order.

Questions to Avoid in your Win Loss Analysis Questionnaire

There are also some questions you should not have in your win loss analysis questionnaire because they don’t add value to the win loss analysis process and can annoy or even anger the customer.

Questions about the Buying Process

Understanding the customer’s buying process is critical to success but by the time you’re running a win loss analysis questionnaire it’s too late to discover that information.

To be of any use that data should already have been uncovered by the sales team. Finding out what it was now is too late for this client and probably not useful for other clients.

So don’t ask win loss analysis questions like that cover topics such as:

  • When did you first go to market to investigate options?
  • What caused you to start looking for a solution?
  • What functionality do you consider must-have vs nice to have?
  • Who in the your (client) organization managed the discovery process?
  • What was the sales timeline?

Questions that Might Annoy the Customer

Remember, people move jobs often and the person you are interviewing might be at another company and back in the market looking for solutions sooner than you think.

Asking them to question or reconsider or validate their decision to you will often put them offside and lower your chances next time around.

So avoid questions such as:

  • Do you feel satisfied by the decision you made?
  • If you had to make the decision all over again, would you have made the same one?
  • What has the post-decision service been like?
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