Win More Business With A Win/Loss Analysis Program

By understanding which steps in your sales process are working and which are not, you can make changes to improve its overall effectiveness.

Chad Perry, Principal
Chad Perry is a seasoned SaaS strategist with a background in marketing and an MBA. He has tripled revenues for companies, contributing to over $1 billion in SaaS revenue. Featured in Inc., TechCrunch, Bloomberg, and more, he blends marketing, sales, and product expertise to shape the future of SaaS marketing.

Key Takeaways

Win-loss analysis is a crucial tool to improve your sales process, identify product/service improvements, and understand customer choices.

A sustainable win-loss program involves regular reviews of wins and losses, using a CRM system for tracking, and incorporating third-party data for a complete picture.

The choice between in-sourcing and outsourcing a win-loss program depends on factors such as time, resources, objectivity, and specialized skills. Both options come with their own set of advantages and challenges.

Win-loss research is vital for understanding why your sales opportunities succeed or fail. Understanding the factors that lead to success or failure will improve your sales process and help you win more business.

With over 20 years of executive marketing, product, and sales leadership — and over $1+ billion in sales revenue credit to my name — I can help you get started (or conduct) a win-loss analysis program that meets your specific needs.

For now, a helpful toolkit is below to help you get started with your win-loss analysis today.

Section 1: Understanding Win-Loss Analysis

What is win-loss research, and what are its benefits?

Win-loss analysis is a systematic approach to understanding the factors influencing the customer buying process and purchasing decisions. Analysis is the process that will help businesses identify which products or services are most popular with customers and why; as well as understand what may need to be adjusted with pricing or product features; or what needs to be done to improve sales of unwanted products or services.

By understanding these factors, businesses can improve their chances of winning more business.

What is win-loss analysis?

Win-loss analysis is the process of reviewing past business wins and losses to identify areas of improvement for future sales pursuits. The goal is to better understand the buying process and why deals are won or lost, so your organization can adjust its selling strategy accordingly.

When done correctly, win-loss analysis can provide invaluable insights that help your sales team close more deals and grow your business.

Why is win-loss analysis important?

There are a number of reasons why win-loss analysis is important for businesses.

  • Better Understand Buying Decisions It can help you better understand your customers and how they make buying decisions. This insight can be used to improve your sales strategy and messaging.
  • Identify Sales Process Areas of Improvement Win-loss analysis can help you identify areas of your sales process that need improvement. By understanding what is working well and what needs to be fixed, you can make changes that will help your team close more deals.
  • Benchmark Against Competitors Win-loss analysis can help you benchmark your performance against your competitors. By understanding how you stack up, you can adjust your sales strategy to win more business.
  • Improve Employee Engagement Win-loss analysis can help improve employee engagement by providing objective feedback on their performance. By understanding what is working well and what needs to be improved, sales reps can be more engaged in their work and feel more motivated to improve their performance.

Who needs win-loss analysis?

Any business that sells products or services can benefit from a win-loss analysis program. That's because understanding why you won or lost a particular deal can help you adjust your sales strategy, improve performance, and close more business in the future.

Win-loss analysis can also be helpful for businesses that are struggling to find new customers. By understanding what your competition is doing right (and wrong), you can adapt your sales strategy and improve your chances of winning future business.

Why are win-loss interviews important?

Win-loss interviews are important because they give you an inside look at what your competitors are doing to win business, and what you can do to improve your own performance. When done correctly, win-loss analysis can help you fine-tune your sales processes, product offerings, and go-to-market strategies.

What are the benefits of win-loss analysis?

Win-loss analysis provides you with insights into your sales process so that you can improve your chances of winning new business. By understanding why you win and lose deals, you can make changes to your sales process that increase your win rate.

Additionally, win-loss analysis can help you identify areas where you need to make improvements in order to be more successful in the future.

Perhaps most importantly, it can help businesses avoid making the same mistakes that led to lost sales in the past.

How can we estimate the ROI of win-loss analysis?

It's important to understand that a win-loss analysis program is an investment, not a cost. The goal of any program is to generate more wins (and revenue) than it costs to implement and maintain. With that said, there are several ways to estimate the ROI of a win-loss analysis program:

  • Compare the cost of the program to the value of a single win. This is the most direct way to compare the two. For example, if your program costs $10,000 per year and you estimate that it helped you win just one additional deal worth $100,000, then your ROI would be 10X.
  • Compare the cost of the program to the increase in win rate. This method is helpful if you don't have a good estimate of the value of a single win. For example, if your program costs $10,000 per year and you estimate that it helped you increase your win rate by 10%, then your ROI would be 10%.
  • Compare the cost of the program to the decrease in loss rate. This method is helpful if you don't have a good estimate of the value of a single win. For example, if your program costs $10,000 per year and you estimate that it helped you decrease your loss rate by 10%, then your ROI would be 10%.

How can we measure the success of our win-loss program?

One way to measure the success of your win-loss program is to track key metrics such as the number of wins, losses, and opportunities.

Additionally, you can track the win rate (the percentage of deals won), loss rate (the percentage of deals lost), and the average deal size.

By tracking these metrics, you can identify trends and patterns over time that can help you improve your win-loss program.

Additionally, you can use surveys and interviews to collect feedback from customers, salespeople, and other stakeholders about the program. This feedback can be used to make improvements to the product and/or program.

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Section 2: Implementing Win/Loss Analysis

How to get started with win-loss analysis

There are many different ways to get started with win-loss analysis. The most important thing is to start collecting data. This can be done through customer feedback, customer surveys, interviews, focus groups, marketing data, or other methods. Once you have data, you can begin to analyze it and identify patterns.

From there, you can start to develop strategies for improving your win rate. This may involve making changes to your sales process, product, pricing, or marketing approach.

How is win-loss analysis conducted?

Win-loss analysis typically involves conducting interviews with customers, prospects, and sales reps.

  • Customer interviews can provide insights into pain points and why they chose your company over others.
  • Prospect interviews can help you understand why you lost a deal to a competitor. They can also help you understand perceived threats, unmet needs, and what the competition is doing that you're not.
  • Sales rep interviews can help you identify strengths and weaknesses in your sales process. It will give you a better understanding of the sales process, what's working and what isn't. It can also help identify any training or positioning needs.

What are the basic steps of win-loss analysis?

There are four basic steps to win-loss analysis:

  1. Collect data. This step involves surveying your customers and conducting interviews with your sales team.
  2. Analyze the data. Once you have collected the data, it's time to analyze it. This step involves looking for trends and patterns in the data.
  3. Identify areas for improvement. After you have analyzed the data, you can identify areas for improvement. This step involves determining what changes you can make to improve your win rate.
  4. Implement changes. The final step is to implement the changes you have identified. This step involves making changes to your sales process and training your sales team on the new process.

What factors to consider when conducting a win-loss analysis

When you're looking to implement a win/loss analysis program, there are a few key factors to keep in mind:

  • First, focus on the quality of your data, not the quantity. A few well-chosen questions can give you more insights than a long survey.
  • Second, don't forget to segment your data. The way customers interact with your product or service will vary depending on their needs and wants.
  • Third, be sure to ask questions that get at the root of why customers chose (or didn't choose) your product or service. This will help you identify areas where you can improve.

How to use win-loss analysis data

You can use win-loss analysis data in a number of ways, but the most common are to improve your:

  • Product strategies
  • Marketing strategies
  • Sales strategies
  • Pipeline management
  • Improve your product strategies

You can use win-loss analysis data to improve your product strategies in a number of ways. For example, you can:

  • Identify customer needs and wants
  • Improve your product positioning
  • Develop new product features
  • Improve your pricing strategy
  • Improve your marketing strategies

You can use win/loss analysis data to improve your marketing strategies in a number of ways. For example, you can:

  • Develop targeted marketing campaigns
  • Improve your website and other sales collateral
  • Create more effective lead-generation programs
  • Improve your sales strategies

You can use win-loss analysis to improve your sales strategies in a number of ways. For example, you can:

  • Analyze your sales process to identify strengths and weaknesses
  • Analyze past wins and lost opportunities to identify success factors
  • Optimize your sales process
  • Benchmark your performance against the competitive landscape
  • Develop targeted messages and positioning for your products and services
  • Identify new market opportunities
  • Improve your buying process

Use win-loss analysis to improve the buying process, by:

  • Examining all the steps in your sales process and customer journey
  • Identifying which steps are working well and which could be improved
  • Making changes to the customer journey based on what you learn
  • Improve your pipeline management

Use win-loss analysis to improve your pipeline management in a number of ways. For example, you can:

  • Identify opportunities earlier in the sales cycle
  • Shorten the sales cycle
  • Increase the accuracy of your sales forecast

The bottom line is that win-loss analysis data can be extremely valuable in helping you improve your sales strategies, win more business, and better manage your sales pipeline. But to get the most out of it, you need to have a clear understanding of what you want to achieve and how you plan to use the data.

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Section 3: Common Challenges and Solutions

Common issues with win-loss analysis and how to avoid them

When setting up a win-loss program, what are some common mistakes that organizations make?

  • Not having a clear understanding of what they want to achieve with win-loss analysis. This is probably the most common mistake organizations make. Without a clear understanding of your objectives, it will be difficult to set up an effective program and to measure its success.
  • Failing to develop targeted messages and positioning for the sales team. One of the key benefits of win-loss analysis is that it can help you develop targeted messages and positioning for your sales force. If you don't have a clear understanding of your target market, it will be difficult to create messaging that resonates with buyers.
  • Not involving the right people in the process. Win-loss analysis should not be done in a vacuum. It's important to involve key stakeholders from different functions within your organization, such as sales, marketing, product management, and customer success. This will help ensure that you have a complete picture of the buyer's journey and can identify areas of improvement.
  • Failing to act on the data. Even the best win-loss analysis program will be of little use if you don't take action on the data. Be sure to establish a process for reviewing the data and taking action based on what you learn.

When to conduct a win-loss analysis

A win/loss analysis should be conducted whenever your company is needing to grow or retain its customer base, or experiencing an influx of lost opportunities. By understanding why you won or lost a particular deal, you can improve your chances of success in future deals and current customers.

How often to conduct a win-loss analysis

Ideally, you should be conducting win-loss interviews on a quarterly basis. This will give you enough data to identify patterns and trends, but not so much data that it becomes overwhelming to manage.

How should we calculate and analyze our win rate?

There's no single answer to this question - it depends on your organization and what you're looking to learn from your win/loss data. However, it is generally recommended to calculate win rates based on both the total number of opportunities (deals) and the total value of those opportunities. This will give you a good sense of not only how often you're winning, but also how much business you're winning.

Once you've calculated your win rates, you can start to look for patterns and trends. Are there certain types of sales opportunities that you're losing more often than others? Are there certain types of customers — or cohorts of customers — that you are winning more often than others? Are there certain salespeople who are consistently losing or winning? By identifying these patterns, you can start to make changes to your sales process and strategies that can help you win more business.

How many sales opportunities do we need to analyze?

Use an appropriate sample size that will be statistically relevant when conducting win-loss analysis. This number will vary, and sample size calculators are prevalent on the Internet.

What are some common pitfalls of win-loss analysis?

Win-loss analysis can be a valuable tool for sales organizations, but there are some common pitfalls that you should avoid. These pitfalls include:

  • Not having a clear purpose for the analysis
  • Not having enough data
  • Not asking the right questions
  • Not taking action on the results of the analysis

If you can avoid these pitfalls, you will be well on your way to using win-loss analysis to improve your sales results.

How do we conduct win-loss interviews?

First, you'll need to decide whether to outsource your win-loss program or handle it in-house. If you choose to go the in-house route, you should have a minimum of two people on your team dedicated to conducting interviews and analyzing results.

Conducting the interviews is often the most time-consuming part of the process, so it's important to have a team in place that can dedicate the necessary time. If you outsource your program to an agency, they will handle all aspects of the interview process for you.

Once you've decided how you'll be conducting the interviews, the next step is to develop a list of questions to ask. There are a few different ways to approach this. You can either develop your own questions or use a pre-existing questionnaire.

If you choose to develop your own questions, it is recommended to start out with a general question about the decision-making process and then branching out from there. Asking specific questions about your product or service is also a good idea.

You'll also want to make sure to ask questions that will help you understand why the prospect chose you or your competitor. Was it due to price? Better product features? A more personal relationship with the sales rep?

Asking these types of questions will help you to identify any areas where you may be falling short.

Once you've developed your questions, the next step is to actually conduct the interviews.

In-person or video interviews are generally considered to be the most effective, but they're also the most time-consuming. Phone interviews are the next best option, followed by email.

The format you choose will ultimately depend on your budget and the availability of your prospects.

Once the interviews have been conducted, it's time to start analyzing the results. This is where things can get a bit tricky. There are a few different ways to approach this, but the most important thing is to be as objective as possible.

Try to look at the results from both a quantitative and qualitative perspective. This means looking at both the numbers (how many people chose each option) and the reasons behind those choices.

Qualitative data can be harder to analyze, but it's often more revealing. Once you've analyzed the results, you'll want to start brainstorming ways to improve your chances of winning in the future.

This is where your team will really need to get creative. If you can identify the root cause of your problem, you'll be much better equipped to fix it.

What questions should we ask in a win-loss interview?

First, yThe questions you ask during win-loss interviews will be based on the objectives of your win-loss analysis. However, there are some common questions that are often asked during win-loss interviews, including:

  • Why did the customer choose our product/service?
  • Why did the customer not choose our product/service?
  • What were the key factors that influenced the decision?
  • Was there anything about our product/service that was a deciding factor?
  • How does our product/service compare to the competition?
  • How satisfied is the customer with our product/service?

How to use win-loss analysis results to improve your sales process?

Sales leaders are always looking for an edge to help them close more business and win-loss analysis is great way to get it.

By understanding why you won opportunities or lost opportunities, you can replicate the winning behavior and avoid the losing behavior in future deals.

By understanding which steps in your process are working and which are not, you can make changes to improve the overall effectiveness of your sales process.

How to create a sustainable win-loss program

When you’re first getting started with win-loss analysis, it’s important to create a sustainable program. Here are some tips:

  • Set aside time each month to review wins and losses. This will help ensure that your program is always up-to-date.
  • Assign someone to be in charge of your program. This will help ensure that someone is always accountable for its success.
  • Use a CRM system to track your wins and losses. This will help you collect and organize your data in one place.
  • Make sure to debrief your entire team after each win or loss. This will help ensure that everyone is on the same page and can learn from each experience.
  • Use a third-party vendor to supplement your own data. This will help you get a complete picture of your wins and losses.

With these tips, you can create a sustainable win-loss program that will help your business succeed.

In-Source vs. Outsource a win-loss program?

When you outsource a win-loss program to an agency, you are essentially paying for someone else to do the work for you. This can be beneficial if you do not have the time or resources to dedicate to conducting a win-loss analysis on your own. However, it is important to note that when you outsource a win-loss program you also lose some control over the process and the results.

What are the pros and cons of working with an internal team?

When it comes to conducting a win-loss analysis, working with an internal team has its pros and cons.

On the one hand, you’re already familiar with your company’s sales process, products, and services. This can make it easier to identify potential areas of improvement.

On the other hand, your team may be too close to the situation to provide an objective analysis. They may also lack the specialized skills and knowledge needed to conduct a thorough analysis.

If you decide to work with an internal team, be sure to choose members who are objective and have the necessary skills and knowledge. You should also put together a plan that outlines what you hope to achieve with the analysis and how you will go about conducting it.

What are the pros and cons of working with a third party?

Hiring an external team to conduct a win/loss analysis comes with its own set of pros and cons.

On the plus side, an external team can provide an objective perspective. They also bring with them a wealth of knowledge and experience that can be extremely valuable.

On the downside, working with a third party can be more expensive than working with an internal team. You may also have to spend some time getting the external team up to speed on your company’s products, services, and sales process.  

If you decide to work with a third party, be sure to do your research and choose a reputable company with experience conducting win/loss analyses. You should also have a clear idea of what you hope to achieve with the analysis and what budget you have to work with.

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Leveraging a win/loss analysis program is pivotal for businesses aiming to refine their sales strategies and better understand customer decisions. Chad D. Perry Consulting, a boutique firm specializing in win/loss analysis, can offer personalized, in-depth insights to navigate complex market dynamics and enhance competitive advantage. The firm's expertise in crafting tailored win/loss analysis programs stands as a valuable asset for companies seeking to improve their win rates and understand loss causes more effectively.

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