How to conduct a win/loss analysis
Once you’ve decided who will conduct the win/loss interviews (the product manager or another objective third party), now it’s time to get started conducting your win/loss analysis.

Before the win/loss analysis interview
First, we have to identify evaluators. Who are evaluators, and how do we find them? Evaluators are the people in your market who have recognized they have a problem to solve and are actively looking for solutions to their problem. They are looking at your solution and at your competitors’ solutions. This is the part of the market that your sales channel is most familiar with; they are active leads in the sales funnel.
Finding evaluators depends on the type of sales channel you use. The more anonymous people are during the sales cycle, the more difficult it is to find them. Use this guide for finding evaluators based on different sales channels.
Next, sit down with the sales team involved in the win or loss. Be sure to include the highest-ranking salesperson in the discussion. Ask for background on the evaluator, including how the company got involved in the proposal, the type of relationship they had/have with them, the sales processes involved, products or solutions used to close the sale, the result and whether they anticipated this result.
Don’t forget to coordinate efforts with other product managers who may also be conducting interviews with the same evaluator. The last thing you want is multiple people reaching out for the same reason. Not only will it annoy the evaluator, but it will also make your company appear disorganized and unprofessional and could jeopardize future sales.
Now you’re ready to schedule an interview with the evaluator. If the evaluator you’re contacting decided not to buy from you, reach out and say something like, “I understand you recently made a decision, and you’re going in another direction. I respect your decision. I wonder if I could get 30 minutes of your time to understand how we could have helped you better for the next time.” This introduction would be even simpler if the evaluator did choose your product. Either way, let the person know in advance the topics you plan to discuss.
During the win/loss analysis interview
When you call the evaluator, start by thanking them for their time and explaining the purpose of the interview (to learn as much as possible about his or her perceptions and experience during the recent sales process so your organization can continually improve). State that you wish to use the evaluator’s feedback within your organization, but he or she should feel comfortable speaking freely because you’ll handle sensitive aspects of your conversation appropriately.
Next, ask the questions you have prepared. These will be specific to your organization, products, sales channels and market, but here are some to get you started:
- Could you please explain your decision-making process?
- Why did you decide to buy/not buy from our company?
- What other companies/products did you consider?
- How did we stack up?
- Which capabilities were most important in your decision to buy?
- What were your thoughts on our proposal/sales process?
- What were your thoughts on the value and pricing of every product you considered?
- What was your perception of our organization prior to entering the buying cycle? Did it change throughout?
- Did you contact our references? If so, were they helpful?
- What advice would you give us for working together in the future?
- What additional comments would you like to share?
Once you ask a question, listen to the evaluator’s answer intently and remain neutral upon hearing their responses. This is a fact-finding mission, not an opportunity to cast doubt on their decision or persuade them to reconsider. Be sure not to challenge or threaten the evaluator’s opinions or perceptions. Do not ask them to justify their decision or correct misinformation.
Remember, perception is reality in sales. If they chose not to buy from you because they thought your product didn’t have the same capabilities as a competitor’s, it doesn’t matter if your product does have the same or even better capabilities. The fact is, they perceived that it didn’t, and that’s the issue that needs to be addressed for future deals.
After the win/loss analysis interview
Once you’ve concluded your interview, send a personal thank-you note to the evaluator. Then, summarize in writing the notes from your interview and distribute them to the appropriate internal team members. Conduct a debriefing meeting and list any action items that need to be immediately addressed. However, unless something egregious comes from an interview, you’ll want to refrain from making any large-scale changes based on one, two or even a handful of interviews.
Repeat
You’ll need a large-enough sample of win/loss interviews to begin to identify patterns. And it’s a numbers game. You must do win/loss consistently to get a sample set that’s large enough. At Pragmatic Institute, we generally recommend doing no fewer than 10 interviews before starting to react to trends.
Once you establish a pattern in your data, it’s important to cast a much wider net. Do something more quantitative, perhaps a third-party survey. You want to validate what you think you have learned in your interviews.