10 Questions to Ask in a Win-Loss Analysis Interview

The Internal Review

You may believe a win-loss analysis, analyzing why one sales effort won the business and another did not, could be a powerful tool to help you build a stronger business, but how do you get started? First, talk with your salespeople to gather background information. For example, make sure you understand:

  • How your company became involved in the proposal;
  • The relationship the sales person has with the customer or prospect;
  • The sales processes they used;
  • The products or solutions they offered; and
  • The end result.

External Interviews

Once you’ve gathered the internal information, it’s time to craft a prospect/client interview that reveals details that may transform your business. Here are a couple of examples we’ve uncovered for clients:

  • One of our client’s competitors was offering big discounts that were knocking our client out of the game every time they competed for large company business in a specific industry. Our analysis revealed that the competition’s strategy was to corner the market for the largest companies in the industry. This called for them to take another look at their pricing strategy.
  • In another situation, the client’s competitor was claiming that their technology was as good as our client’s solution; tests proved it was not. We learned the messaging needed to better define their product’s differentiation and superiority.

10 Questions to Ask Prospects and Clients to Inform Your Win-Loss Analysis

What was the opportunity?

You want to understand clearly why the prospect or client came to you. What problem were they trying to solve?

How well did your company solve the problem?

Your company likely offered a solution to a problem. But was just adequate, or did it wow them and exceed their expectations?

Which companies were in the competitive mix?

Wouldn’t you like to know what you’re up against when you compete for business? Find out which companies were in the mix and why your company did or didn’t get the business.

How was the decision made?

If you understand the decision-making process, you can tailor your sales and marketing tactics better to meet prospect needs—providing the necessary information to the right people when they need it.

What were the selection criteria?

By asking this question you learn what was really important to your prospect. You may discover that there are areas where your product or solution is lacking, or other attributes that are over-engineered, forcing the price above the competition. Discover what’s really of value so you can provide it.

How did your customer or prospect perceive how your sales team managed the sales process?

If your sales team dropped the ball, they are likely to gloss this over in conversation with the management team. But the customer can give you their side of the story. You may discover issues in the sales department or, perhaps, problems with your internal team that supports your sales representatives.

How impressed was the prospect or client with your proposal and presentation?

Even if you can do the job well, if this doesn’t come across in your proposal or presentation, you likely won’t receive the contract. Probe to discover the plusses and minuses from the prospects’ viewpoint. Were they comfortable with your qualifications? What capabilities are most critical for them?


How did your pricing compare to your competition’s pricing? Did the prospect perceive that you offered good value or was your solution over priced? Also, were you priced so much below your competitors that they were concerned about quality?

Did they call your references?

Find out whether or not your prospect or client called your references and how that affected their decision.

Would they recommend your company?

This question is the true test. Someone will only recommend your company to others if they are really impressed. Whether the answer is “yes” or “no,” find out the “why” behind the response.

With the answers to these questions, a strong picture will emerge that from your win-loss analysis, enabling you to move forward more intelligently in the future. For more information about 3D2B, visit www.3D2B.com or call 1 718-709-0900 or +39 06 978 446 60 (EMEA).