The 31 Best Win-Loss Questions You Should Be Asking

What are the best questions to ask during a sales win-loss analysis interview?

An honest starting point for anyone looking to bone up on B2B win-loss analysis.

At the same time, this is the completely wrong way to go about it. 

There will never be a list of questions that perfectly suit every win-loss interview. 

That said, there are absolutely several best practices for win-loss analysis that, when followed, will set you and your program up for success.

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Ask Win-Loss analysis questions covering the entire buyer journey

No matter what, make sure you’re asking questions that acknowledge every step in the buying process. 

Generally, there are 10 steps in the buyer journey you need to consider when conducting a win-loss analysis interview.

best b2b win-loss analysis questions

The Role: 3 Win-Loss Analysis Questions

  1. How did you play a role in the evaluation process?
  2. What are your responsibilities above and beyond evaluations like these?
  3. Tell me about your previous experience with vendors like us. 

Awareness: 3 Win-Loss Analysis Questions

  1. What made you realize you needed a vendor partner in this space?
  2. How many voices at your company were asking for a change that led you to evaluate your options?
  3. What were the main issues with your previous vendor partner (if applicable)

Evaluation Bias: 3 Win-Loss Analysis Questions

  1. What did you think of our company before the evaluation started?
  2. What did you think of [insert competitor] before the evaluation started?
  3. How have your thoughts about our company, our competitors and the space in general changed over time?

Requirements: 3 Win-Loss Analysis Questions

How did you go about requirements gathering?

How well did [company] align with your requirements?

What were your must-haves?

Consideration: 3 Win-Loss Analysis Questions

  1. Who else did you evaluate in your decision? 
  2. Explain the factors that helped narrow down your decision-making.
  3. What were the strengths and weaknesses you saw across all vendors?

Buying committee: 3 Win-Loss Analysis Questions

  1. Who was responsible for what in the buying process?
  2. Who were the most influential people in the decision-making process?
  3. How do you think the buying process would have been different had there been fewer voices at the table?

Product Demo: 3 Win-Loss Analysis Questions

  1. What was the most memorable part of the demo experience
  2. How did our demo compare with some of the other finalists?
  3. What would you have like to see more of?

Products and Services: 3 Win-Loss Analysis Questions

  1. How would you describe our company’s product strengths and weaknesses?
  2. How much was customer service emphasized during the evaluation process?
  3. What would make our product better?

Price: 3 Win-Loss Analysis Questions

  1. How did our pricing model compare to our competitors?
  2. How important was price to you and your team in the first place?
  3. To what extent did you feel like our pricing matched the value we offered?

Sales Process: 3 Win-Loss Analysis Questions

  1. What was missing from the sales process and what did you like about it?
  2. How did our sales process differ from others?
  3. How can we make our sales process more effective?

That’s only 30 win-loss analysis questions…

Guilty! There is indeed a 31st question. It’s one that comes at the end of your interview — and happens to be the most fun of the bunch. 

If you want to check that question out, as well as 50 others, download our Win-Loss Interview Toolkit & Checklist.

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