By Graham Goodwiler


Win/loss analysis is a critical component of competitive intelligence that helps businesses understand why they win or lose deals. This analysis can provide insights into the effectiveness of sales and marketing efforts, customer preferences, competitive strategies, and market trends. By conducting a thorough Win/Loss analysis, companies can identify areas for improvement and develop effective strategies to gain a competitive edge. In this blog post, we will discuss the benefits of Win/Loss analysis and some advanced methods to take it up a notch.

In this article we’ll cover:

  • What is Win/Loss Analysis?
  • Benefits of a Structured Win/Loss Analysis Approach
  • Advanced Methods and Tips for Success 
  • Outcome-oriented Questions for Win/Loss Analysis
  • Recommended Readings


What is Win/Loss Analysis?

Win/Loss is an easy, yet exceedingly effective methodology for understanding why you are winning and losing deals. Due to its simple purpose, anyone with a customer can, and should, apply it. Most commonly, it is a process that sales and marketing teams apply; however, just about everyone does some version of selling, meaning just about everyone has to influence others within their professional and personal lives. 

We think of Win/Loss analysis as a more structured form of feedback. It can be as simple as going to a customer or decision-maker and asking “What do you like/dislike?,” “What went well/poorly?,” or “What else would you like to see?” Many of us incorporate this sort of quick feedback naturally into conversations and we use them to help us and our work continue to improve.

Benefits of a Structured Win/Loss Analysis Approach

Making that simple feedback process more structured and less anecdotal is called Win/Loss analysis. With more rich data and a sample that can be extrapolated to the larger population (i.e., your serviceable obtainable market – SOM), you can: 

  1. Understand customer preferences and buying behavior –  Win/Loss analysis helps companies understand why customers choose their products or services over competitors’. It can provide insights into customer preferences, decision-making processes, and buying behavior, enabling companies to tailor their products, services, and marketing messages accordingly.
  2. Identify competitive strengths and weaknesses – Win/Loss analysis can help businesses identify their competitive strengths and weaknesses. By analyzing the reasons for winning or losing deals, companies can gain a better understanding of how they stack up against competitors and develop strategies to improve their competitive position.
  3. Improve sales and marketing effectiveness – Win/Loss analysis can help companies identify areas where their sales and marketing efforts are falling short. By understanding why deals are lost, businesses can develop more effective sales and marketing strategies that address customer needs and preferences.
  4. Enhance product development – Win/Loss analysis can also provide insights into product development. By analyzing customer feedback and preferences, companies can identify areas where their products can be improved or expanded to meet customer needs.

As you can expect with a methodology that has a general purpose and many potential outcomes, there is no “one size fits all” approach. It should be contextualized to your specific goals, customers, and products. 

Like with anything, the more purposeful you are with W/L, the more you’ll get out of it. Really focus on clarifying your end goals and what buy-in you’ll need to actually make change. It’s also important to have a little humility check: Are you really willing to accept whatever results come in? What will you do if the consensus is that your product is subpar and difficult to use? What will you do if you hear that your sales people are pushy and rude? If any one of those things come up, are you going to dismiss them and say that person didn’t know what they’re talking about, or will you actually listen to them, accept that things can be improved and work on it? 

Advanced Methods and Tips for Success

To conduct a successful Win/Loss analysis, businesses should consider the following advanced methods and tips:

  1. Focus on both wins and losses – To gain a comprehensive understanding of why deals are won or lost, businesses should analyze both successful and unsuccessful sales efforts. By analyzing successful sales, companies can identify their competitive strengths and best practices, while analyzing unsuccessful sales can highlight areas for improvement. 
    • If you want to take this up a notch, you can also survey people within your target market that have no idea who you are, or multi-wallet consumers who’ve tried out multiple products in your space.  
  2. Use multiple data sources – To ensure a thorough analysis, businesses should use multiple data sources, including customer interviews, sales team debriefs, and competitive research. By triangulating data from multiple sources, businesses can gain a more accurate and comprehensive understanding of why deals are won or lost.
    • Another way to build a more robust dataset is to use experienced, third-party interviewers with elicitation expertise. These highly-skilled individuals will be able to provide extremely rich insights, well beyond those that you’ll receive by just using a standard set of questions. 
  3. Develop a standardized process – To ensure consistency and accuracy, businesses should develop a standardized process for conducting Win/Loss analysis. This process should include clear guidelines for data collection, analysis, and reporting, as well as a defined timeline and team roles and responsibilities.
    • While the information should be consistent to be measured and compared over time, you also need to be agile with your approach and continue to iterate the process. As priorities change, your questions and process should reflect those changes. Maintaining a few consistent questions while rotating out questions reflecting current needs is one way to go about this tradeoff. 
  4. Focus on actionable insights – To derive the most value from Win/Loss analysis, businesses should focus on actionable insights. These insights should be specific, measurable, and directly tied to business goals and objectives. By focusing on actionable insights, businesses can develop effective strategies to improve their competitive position and win more deals.
    • To make Win/Loss insights actionable, it’s critical to build buy-in from those above, below, and lateral to you in the organization. Getting others involved in the process by asking them what they need to know, seeing what questions they’d like to get answered, and democratizing the anonymized results are great ways to build influence and ensure your Win/Loss program achieves its goals.

Outcome-oriented Questions for Win/Loss Analysis

The trick to Win/Loss analysis is to be as purposeful and outcome-oriented as possible with your questions. People only have so much time they’re willing to give you and survey fatigue is a real thing. For variety, it’s helpful to mix up quantitative (e.g., On a scale of 1-10, how likely are you to recommend our business to a friend or colleague?) and qualitative (e.g., What confused you when you were first learning about our product?) questions to get measurable, as well as rich results. To that end, below are a few questions that we at Aurora WDC have utilized to build actionable insights from a Win/Loss interview. 

  • “Where did __ fall short of your expectations?”
    • With this question, you can see what it was that disqualified you or others from their checklist. If you didn’t meet this criteria then you had no chance of getting a further look.
  • “What are one or two characteristics that ultimately drove your choice?”
    • Here you can see where your product was better or worse than the alternatives. These were their key decision factors – it’s typically a tradeoff between price and quality of service, but there are other factors as well that we consider when making our final decision. 
  • “What things from ___ surprised you that you found attractive?” or “What things surprised you that you found puzzling or confusing?”
    • This is helpful for messaging and may help with your product’s focus/roadmap going forward. It’s helpful to know, from a customer perspective, where your product is unique from the competition.
  • “What’s the one thing you would change about the product or your experience with us?”
    • This gets to their core opinion about your company and helps to make them feel heard and valued. If you see multiple people saying the same thing, then it’s definitely something to address immediately. 
  • “What do you wish we would have said (or said earlier) during the demo that would have made us the obvious choice?”
    • This question is another way of getting at what they were really looking for in your product or service. Sometimes you even have what they wanted, but your sales team didn’t know to emphasize that. Asking it this way also gives them a “magic wand,” giving them the opportunity to think more and potentially give you information that was in their head but not explicitly stated before. 

Recommended Readings


As you can see, Win/Loss analysis can be a highly effective program for competitive intelligence and applied research that provides businesses with valuable insights into why they win or lose deals. By conducting a thorough analysis, applying advanced methods, and utilizing outcome-oriented questions, you can create a Win/Loss program with asymmetric insights that can directly feed into many decisions, choices, actions, plans, and strategies within your organization.