Tips for Conducting a Win-Loss Analysis

Tips for Conducting a Win-Loss Analysis

There are many reasons why prospects accept or reject your proposals and bids. Perhaps, it was the economy, or the right product at the wrong time. Maybe it was the price, or your seller couldn’t sway a decision maker.

That’s what makes a win-loss analysis essential. It is the process organizations undertake to understand why a customer bought your product or service. It also explains why they chose not to. This information is vital to measuring the long-term implications of a won or lost deal. It’s key to making corrections to maintain or improve your position and grow your business. Here, let’s examine some tips for conducting a win-loss analysis:


According to, only 42 percent of companies regularly conduct a win-loss analysis. One reason could be the time and effort it takes. When you consider the process, including interviews, questionnaires, and surveys, it can be a lot.

Here, it is important to note a win-loss analysis is not about assigning blame. This would make it a negative process, not only for your sellers. Your buyers too may be hesitant. Instead, a win-loss analysis is an overall evaluation. It can provide your organization with valuable insight into several key areas. These include:

  • Sales process
  • Buying process
  • Competition
  • Marketing
  • Product development
  • Finance

A win-loss analysis can reveal your customer’s perspective of your sales process. For example, it can address how your sales team engaged the prospect. Did they build relationships? Address needs? Did they invest the time required to understand the customer? Most importantly, did the customer feel valued and appreciated?

Another consideration is how well your sales process aligned with the buyer’s journey. Today, the buyer’s journey is increasingly complex. For one thing, buyers are better educated. Also, there are more decision makers. Now, more than ever, it’s incumbent on sellers to match their sales process to the buyer.

In addition, the competition is greater. Educated buyers know their options. Sellers must not only be familiar with their own products and services. They must better understand the competition to differentiate their own. They must clearly demonstrate the features and benefits. And they must show their value over a buyer’s current product or potential replacement.

A win-loss analysis also offers insight into your marketing efforts. This includes effective messaging, accurate buyer personas, and attractive value propositions. It includes the content your sales teams delivered. Was it timely and pertinent? Did it generate interest and help buyers make informed decisions?

A win-loss analysis can show if your products and services meet the needs of your customers. Also, how do they rate your features and benefits? This is critical for your L&D teams and product development.

In addition, price is often a major objection. A win-loss analysis can reveal what buyers thought of your price points in relation to value.

Common Mistakes

The mistakes organizations make when conducting a win-loss analysis often center on the approach. A half-hearted analysis will not yield useful information. Instead, organizations must invest. This means viewing their win-loss analysis as a vital tool in their ongoing assessment.

Additionally, the entire organization should buy-in to the process. This includes the C-suite, sales managers, and sales reps. All should appreciate the value of improving performance and, most importantly, win rates. Some common mistakes include:

  • Lacking clear objectives
  • Not asking the right questions

Start with a clear set of goals and objectives. Without these, your analysis is a fishing expedition. Consider the things you really want to know. This should include information about your processes, products, and people.

In addition, ask the right questions. This includes documenting the questions and formulating them for maximum effect. For example, avoid closed-ended questions. These can be answered yes or no and might not be useful. Instead, use open-ended questions that invite explanation. Rather than, “Did you find the salesperson helpful?” ask, “Can you describe the salesperson’s helpfulness?”

Ensure Accurate Feedback

Accurate feedback is essential. Stronger input yields superior output. Here, consider the following:

  • Set up
  • Sample size
  • Facilitator

Your set up is key. Be forthright. Tell the customer you are conducting a win-loss analysis. You seek the reasons you achieved the sale or missed out. Assure them you want the truth, and their answers will better enable you to meet their future needs.

Sample size is important. Contact the people who can best answer your questions. This is not limited to your seller’s lead contact. It should include key decision makers, like managers, tech specialists, and other VIPs. A small sample size can result in skewed data. A wider net ensures you reach the right people and receive reliable data.

Often, your salesperson is not the best choice to facilitate a win-loss analysis. Of course, their input is important, and they should be part of the process. But they can be too close. Their investment is too great. If you want customers to speak candidly, consider high-level interviews, such as executive to executive. You could also hire an outside vendor to ensure you receive accurate information.

Best Practices

Following is a list of best practices for conducting effective win-loss analyses:

  • Brevity
  • Know decision makers
  • Standardization
  • Ensure an on-going process
  • Thank/compensate customers

Keep it short. Your customers are busy. Show them you value their time. Ideally, do not exceed 30 minutes. This is plenty of time to address the biggest issues.

Make sure you talk to a decision maker or someone with a high degree of influence. Remember, you’re asking about buying criteria. You want someone who knows this information and was invested in the process.

Have a standard set of questions. These should be thoughtful and geared to the information you seek. Also, be consistent in your approach. This helps you better understand the data in relation to other customers and deals.

A win-loss analysis should be an ongoing process, not a one-time event. High-performing sales organizations know the value of regular customer feedback. This ensures your sales team consistently meets and exceeds customer expectations.

In addition, thank your customers for their time. This can be as simple as a follow-up email, small gift, or other compensation. Be generous. After all, customer feedback is vital to improving your business. Also, today’s lost deal can return as tomorrow’s best customer.


Interviews are the best way to get the information you need. Open-ended questions allow customers to go deeper in their responses. However, many organizations supplement their interviews with technology. Consider the following:

  • Questionnaires and surveys
  • Segmentation/demographics

Questionnaires and surveys can reach a wider audience and reveal more specific, quantitative information. Types of surveys vary from simple “Yeses” or “Noes” to a dichotomous, two-point scale of opposites or more complex Likert scales. Today, there are many tools and software that can help.

In addition, surveys can segment the data across groups. Consider the demographics. There may be differences between customer size, location, buyer type, and even competitors. Often, a customer’s perception of your organization will change based on the competition. You might have been number one against some but number three against others. This can improve your process and pitch.

Clozd research revealed B2B decision makers are more likely to participate in interviews (30 percent of the time) over surveys (5 percent). This is even though interviews require more time than surveys.

For sales organizations, success is never a zero-sum game. It’s not only based on whether you closed the deal. Sure, closed deals are better than lost ones. But in both cases, the reasons are important. For one thing, real success is based on consistency. To sustain growth, you must know what worked and what didn’t. And you must be willing to make the changes needed to improve. We hope this helps your organization conduct productive win-loss analyses to better serve customers and close more deals.

Interested in learning more about adopting Win/Loss Analyses in your sales process? Join us on September 13 for a panel discussion with Clozd. We will address how sales managers can utilize win-loss data to improve performance and processes.