Sep 10, 2024

25 Win-Loss Analysis Interview Questions

Written by

Andrew Luo

What is win/loss analysis?

Win/loss analysis is a strategic process used by businesses to evaluate the outcomes of their sales efforts. It involves systematically examining both successful and unsuccessful sales opportunities to gain insights into the factors that influence customer decisions. This analysis helps companies understand their competitive position, refine their sales strategies, and improve their overall performance in the market.


Before the interview

Before conducting a win/loss analysis interview, it's crucial to prepare thoroughly. This preparation ensures that you gather meaningful insights and make the most of your time with the interviewee. Here are some key steps to consider:

  • Research the specific deal and customer to tailor your questions appropriately

  • Review any existing data or feedback related to the deal

  • Prepare a structured interview guide with open-ended questions


Incentives

Offering incentives to participants can significantly increase the response rate and quality of feedback in win/loss analysis interviews. Consider providing:

  • A gift card

  • Something that fits the buyer persona (i.e. set of golf balls, bottle of wine)

  • A discount on future purchases (if the deal was closed won)


Win-loss analysis questions

Here are 25 questions you can ask in your next interview, broken down by category. Be sure to adjust the questions to fit the persona and context of the deal.


Pricing:

  • How did our pricing compare to other options you considered?

  • Was our pricing structure clear and easy to understand?

  • Did you feel our product offered good value for the price?

  • Were there any specific pricing concerns that influenced your decision?


Product:

  • What were the key features you were looking for in a solution?

  • How well did our product meet your specific needs?

  • Were there any critical features missing from our product?

  • How did our product compare to competitors in terms of functionality?


Sales Process:

  • How would you rate your overall experience with our sales team?

  • Did you feel the sales representative understood your needs?

  • Was the information provided during the sales process clear and helpful?

  • How responsive was our team to your questions and concerns?


Implementation and Support:

  • What were your expectations regarding implementation time and complexity?

  • How important was the level of customer support in your decision-making process?

  • Did you have any concerns about potential integration issues?


Company Reputation and Reliability:

  • How familiar were you with our company before the sales process?

  • Did our company's reputation influence your decision?

  • How important was the long-term viability of the vendor in your decision?


Decision-Making Process:

  • Who were the key decision-makers involved in the selection process?

  • What were the primary factors that influenced your final decision?

  • At what point in the process did you make your decision?


Competitive Landscape:

  • Which other vendors or solutions did you consider?

  • What made you choose the winning solution over ours (in case of a loss)?

  • Were there any unique offerings from competitors that stood out to you?


Future Considerations:

  • Is there anything we could have done differently that might have changed your decision?


Your next interview

When preparing for your next win-loss analysis interview, keep these key points in mind:

  • Review the questions above and select those most relevant to your specific case

  • Tailor the questions to the interviewee's role and their involvement in the decision-making process

  • Be prepared to ask follow-up questions to dig deeper into interesting or unexpected responses

Check out our blog for more on win/loss!

Start learning from
closed deals with Hindsight

Improve your product roadmap, sales processes, and competitive positioning by collecting and aggregating feedback.

Start learning from
closed deals with Hindsight

Improve your product roadmap, sales processes, and competitive positioning by collecting and aggregating feedback.

Start learning from
closed deals with Hindsight

Improve your product roadmap, sales processes, and competitive positioning by collecting and aggregating feedback.

Start learning from
closed deals with Hindsight

Improve your product roadmap, sales processes, and competitive positioning by collecting and aggregating feedback.