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How to do win-loss analysis

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Looking to implement win-loss analysis for the first time? We can help. Here's a list of answers to common questions you may have about win-loss analysis. Further down, we provide links to helpful resources that can help you get off to a strong start.

What is win-loss analysis?

Win-loss analysis is the practice of systematically capturing and analyzing feedback about why you win and lose sales opportunities. Effective win-loss analysis helps you uncover the truth about why buyers do or do not purchase your products or services. Knowing and acting on this insight will improve sales performance, marketing effectiveness, product strategy, strategic alignment, and more.

Who needs win-loss analysis?

Win-loss analysis is a mission-critical practice for any organization that wants to improve its win rate. If your organization has a sales team and a CRM system then you should be conducting win-loss analysis on an ongoing basis. Win-loss analysis provides valuable insights and benefits for many teams and departments across a typical organization, including:

Win-loss analysis helps boards and executive teams make strategic decisions based on data instead of conjecture.

Sales Leaders 
Win-loss analysis helps sales leaders improve coaching, optimize sales processes, and defend the requests they make of other functions (i.e. content, pricing, new features).

Win-loss analysis helps marketers improve content and messaging by deepening their understanding of buyer needs, decision criteria, competitors, etc.

Product Managers 
Win-loss analysis helps product leaders hone product strategy and prioritize roadmap with more confidence by exposing the real strengths and weaknesses of their solution. 

Product Marketers 
Win-loss analysis equips product marketers with the data and insights they need to optimize product messaging, product strategy, and sales enablement. 

For a more comprehensive list of roles that benefit from win-loss analysis, explore the introductory section of The Definitive Guide to Win-Loss Analysis. Download a free copy here.

What are the basic steps of win-loss analysis?

The goal of win-loss analysis is to analyze why you are winning and losing sales opportunities.

To get started, follow these steps: 

1. Secure Executive & Cross-Functional Sponsorship

The first step of an effective win-loss program is to secure the support and buy-in of your executive team and any key functional leaders. Win-loss programs that are sponsored by the C-suite are more likely to receive the funding they need, drive change across multiple departments, and achieve a meaningful ROI for the business. 

2. Choose the Right Win-Loss Data Channels

The second step is to determine the right sources of win-loss data to analyze. For most organizations, there are 3 sources of useful win-loss insight: CRM data (quantitative), sales team feedback (qualitative), and buyer feedback (qualitative). The richest insight comes from buyer feedback, but ideal programs tap into all three sources. For more details on these win-loss data sources, and how to implement them, download The Definitive Guide to Win-Loss Analysis by clicking here

3. Determine the Right Questions to Ask

After choosing the right data channels, your next step is to determine the right questions to ask. Good question design enables better analysis, higher data quality, and higher participation rates. For sample win-loss interview questions, visit the Best Practices section of this learning center. 

4. Build an Operational, Ongoing Program

Once your data channels and question methodology are solidified, it’s time to start collecting the data. Successful win-loss programs are ongoing initiatives, not one-off analyses or projects. Build a process that enables continuous collection of win-loss data so that you can monitor why you win and lose over time. 

5. Prioritize Getting Started, Not Being Perfect

Not all organizations are ready to implement a comprehensive win-loss program right away. It’s better to start somewhere than never starting at all. So, if needed, focus on getting started. Consider focusing your efforts on a narrow business segment or product line. Then, expand your efforts over time.

6. Integrate & Interpret the Results

Once the data is flowing, you need to invest time and effort to extract meaningful insights. Implement a system for logging positive and negative decision drivers that influenced each opportunity outcome. Then, aggregate and analyze those decision drivers across many opportunities. Look for common themes and trends. Filter the results based on important business factors (i.e., segment, product line, geography, etc.). Monitor how the data changes over time.

7. Share the Findings Widely to Drive Action

To ensure that your win-loss insights drive action, you should embrace feedback sharing and transparency. Share the win-loss feedback with leaders across your business. Implement tools and processes that push relevant insights to these stakeholders in real-time. For more tips on turning win-loss insight into action, check out the Best Practices section below.

8. Measure Your Success

Monitoring the success of your program can be the most exciting and rewarding part. Monitor decision drivers to see if any evolve from weaknesses into strengths. Track your sales win rate to see if it improves over time. Ask for feedback from key stakeholders about the value they are getting from the program and how you could make it better. To better understand the potential ROI of an effective win-loss program, check out the ROI & Benefits section of this learning center. 

For in-depth guidance on each of the 8 steps listed above, download a free copy of The Definitive Guide to Win-Loss Analysis by clicking here.

What are the best sources (quantitative vs. qualitative) of win-loss insight?

For most organizations, there are 3 sources or channels of win-loss insight: 

  • CRM data.
  • Buyer feedback.
  • Sales team feedback.

Your CRM can provide quantitative data to answer basic questions like: 

  • What is our win rate? 
  • What types of opportunities are we most likely to win? 
  • What types of opportunities are we most likely to lose?
  • What is our average deal size?
  • How many opportunities do we win and lose each period? 
  • Are these figures changing over time?

But, to figure out why you win and lose sales opportunities you must capture qualitative feedback from the parties that were involved in the sales process - especially the buyers. Buyers are the richest and most accurate source of feedback about why you win and lose. Every effective win-loss program centers on feedback from the actual decision-makers at won and lost accounts. The sales team is a useful source of secondary feedback about why you win and lose. Their internal perspective can add additional context to the feedback you receive from buyers, but shouldn’t replace it.

To learn more about these data sources, and to get step-by-step guidance on using surveys vs. interviews to capture this feedback, download The Definitive Guide to Win-Loss Analysis by clicking here.

Why are win-loss interviews important?

A win-loss interview (with the buyer) is the best way to uncover what really drove the outcome of a specific sales opportunity. That’s because most B2B purchase decisions are complex, with several decision drivers playing a role in the eventual outcome. An interview helps you capture the buyer’s full story, including all the factors that influenced their final decision.

Win-loss interviews are important because:

  • They enable buyers to expound fully about their decision-making process.
  • They allow interviewers to ask probing follow-up questions on the fly.
  • They have higher average participation rates than surveys (30% vs. 5%).

Additionally, buyers usually spend much more time participating in a win-loss interview than a win-loss survey. In most cases buyers spend 30 minutes in an interview versus 3 minutes in a survey. For these reasons, some organizations build win-loss programs based entirely on win-loss interviews. But, depending on the volume of closed opportunities you have it may be cost-prohibitive to interview every closed opportunity. So, you might choose to deploy a combination of interviews and surveys. For additional guidance on win-loss interviews, check out the Best Practices section of this learning center.

How should we calculate and analyze our win rate?

For a simple metric like win rate you may be surprised to discover that there are various accepted definitions:

Win Rate by Count
# of Wins / # of Closed Opportunities

Win rate by count is the ratio of deals won to the number of total closed opportunities for a given period. Win rate by count answers the question, “how often do I win?” For example, if your sales team closed 8 deals last month and only 2 were wins, then your win rate by count would be 25% (i.e., 2/8 = 0.25).

Win Rate by Amount

$ of Wins / $ of Closed Opportunities

Win rate by amount accounts for the amount/value of each opportunity. In other words, divide the total amount of all wins by the total amount of all closed opportunities for the period. Using the same example above, assume the 2 wins totaled $80,000. Assume the sum total of all 8 closed deals was $140,000. Your win rate by amount would be 57.1% (i.e., 80,000 / 140,000 = 0.571). Notice that the win rate by amount is significantly higher than win rate by count because the two wins were relatively large deals. Thus, win rate by amount answers the question, “what percent of the dollars in our pipeline are we winning?”

Including Open Opportunities

The two methods above are complementary because they only include “closed deals” in the denominator. In a recent survey, this was the preferred approach for 80% of companies.

However, 20% of companies said that they include all opportunities (i.e., open and closed opportunities) in the denominator of their win rate calculation like this:

# of Won Opportunities / # of All Opportunities

$ of Won Opportunities / $ of All Opportunities

This alternative approach incorporates all opportunities, including those that are still open in the sales process. At Clozd we advise against this approach because it includes opportunities that may eventually become wins. Thus, it can substantially understate your true win rate.

Additional Analysis

On their own, win rates are a useful metric for benchmarking sales performance over time. To get even more value from your analysis, you should apply additional context to derive deeper insights.

  • Apply time to your analysis. If you monitor win rates over time (i.e. by quarter) you will begin to notice trends. You may observe that win rates are steadily improving.
  • Apply geography to your analysis. If you break win rates down by sales region or territory then you may notice trends, like certain regions outperforming others.
  • Apply customer segmentation to your analysis. If you break win rates down by customer segment then you may notice additional trends, like higher success rates selling into certain verticals or industries.
  • Add a competitor dimension to your analysis. If you track the competitors that are in play for each opportunity then you can analyze competitive trends. Compare win rates by competitor to determine which competitors are the hardest and easiest to beat.

If you need help calculating and monitoring your win rate, contact us for a demo of our innovative software tools for monitoring and analyzing win rates.

Best practices

Ready for the next step? This section explores best practices to help you improve the quality, scope, and impact of your win-loss program. We also provide resources (videos, content, etc.) that can help you take your program to the next level.

How many sales opportunities do we need to analyze?

One of the most important questions we get from our clients is, “how many win-loss interviews do we need to conduct to achieve statistical significance?” In other words, they want to know what minimum sample size is adequate to draw sweeping conclusions about why their business wins and loses.

If you are resource-constrained or finding it difficult to get started, some win-loss data is always better than none. Hearing from one customer is better than none. As you expose compelling insights, you will garner support and buy-in for a broader program. If you only have bandwidth or resources to conduct a limited number of win-loss interviews, try to focus your efforts on a small, well-defined segment of your sales pipeline. As you focus, you will likely uncover actionable insights for that segment within 15-30 interviews.

However, these targeted projects won’t achieve the broader goal of ongoing, executive-level visibility into why your company wins and loses. To achieve this, you’ll need to broaden your initiative to cover your entire sales pipeline. This is because every customer story is unique and there are many sub-segments of your business that have different win-loss themes based on factors like use case, geography, customer segment, product line, etc. You will only make these discoveries if you solicit feedback from every sales opportunity. Thus, the quality of your win-loss program is better measured by pipeline coverage than sample sizes.

To achieve substantial pipeline coverage, you may need to tap into several win-loss data channels including buyer interviews, buyer surveys, and sales team feedback. For a detailed guide to constructing a multichannel win-loss program, download a free copy of The Definitive Guide to Win-Loss Analysis here. You can also schedule a free consultation with a member of our team by clicking here.

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

A win-loss interviews allow you to dive deep and fully understand the decision drivers that dictated the outcome of a specific sales opportunity. An effective win-loss interview resembles a conversation, not a survey. Before conducting any interviews, develop an interview guide that outlines the key topics and questions you want to incorporate into each conversation. Consider questions like these:

Overview & Origination

What was your final decision? Why?

What prompted your evaluation?

How did you structure and run your evaluation?

Product or Solution

What specific requirements did the product/solution need to meet?

Which capabilities were most important to you?

What were your impressions of the overall product offering?

What were its strengths? Weaknesses?

Sales Experience

What was the overall buying experience like?

What did the sales team do well? What could they improve?

How did the sales experience influence your final decision?

Pricing & Packaging

How did you react to the initial pricing proposal?

How did you view the price relative to the overall value?

How did the price compare to that of other vendors?

Did the pricing model align with your needs and expectations?


What other vendors did you include in your evaluation?

Win: Which vendor was the strongest alternative?

Loss: Which vendor did you choose?

In what ways did <vendor> excel? Fall short?


If you were the CEO of <company>, what would you change?

Win: How satisfied are you with the experience so far?

Loss: What could <company> change to win your business in the future?

To ensure success, spend time preparing additional win-loss questions that will help you dig deeper in specific scenarios. For example, if your company sells marketing software, you have probably seen how vital the software’s ability to integrate with other platforms is to some buyers. You should develop targeted questions to ask whenever a buyer mentions integrations as a critical feature in their decision. Avoid asking a question like, “Are integrations important to you?” Instead, ask an open-ended question like, “What are the most important integrations to you and why?"

For a more robust guide to win-loss interview questions, check out this blog post or download a copy of The Definitive Guide to Win-Loss Analysis here. We also recommend this webinar about conducting effective win-loss interviews.

How can we automate and scale our win-loss program?

Successful win-loss programs are ongoing initiatives rather than one-off analyses or projects. A recent Gartner report emphasized the importance of continuous win-loss measurement by saying, “Managers implementing a strategic win/loss analysis program must make sure valuable and sustainable flows of objective feedback are created to support the process. Win/loss analysis programs often fail when trying to deliver a short-term fix … create a survey instrument and process that are oriented toward an extended time horizon.”

General tips for automating and scaling your win-loss program include:

  • Start with good CRM data hygiene. Make sure your sales team logs each closed opportunity. Encourage them to enter accurate information for the primary contact(s) at each account. This data is a crucial foundation for win-loss analysis.
  • Create CRM reports that monitor and analyze your win rate(s) in real-time.
  • Implement a CRM feedback mechanism for collecting sales feedback about each closed opportunity. This can be accomplished with CRM-integrated survey tools, custom CRM fields, or an app like Clozd.
  • Automate interview and/or survey invitations to the primary contacts at each closed opportunity. This can be accomplished with CRM-integrated survey tools, like GetFeedback, or an app like Clozd.
  • Record and transcribe win-loss interviews using tools like Zoom, Rev or Otter. 
  • Consolidate the internal and external feedback about each opportunity and share the summaries with stakeholders across the organization.
  • Roll up key insights on a weekly or monthly basis in a format that is easily accessible to key stakeholders across your organization.

Automating and scaling a win-loss program is possible, but not easy. That is why Clozd offers an innovative platform for capturing and consolidating win-loss data in a way that’s easy to access and share across your organization. For more information, request a demo of the Clozd platform here.

What strategies/tactics can help us turn win-loss insight into action?

To ensure that your win-loss insights drive meaningful action, you should give win-loss data access to a large number of stakeholders. Promoting a culture of transparency with win-loss data will promote valuable internal dialogue and can help you achieve the greatest possible outcomes.

Tactics for sharing win-loss insight effectively include:

  • Automatically alert leaders each time a win-loss summary for a key account is published.
  • Roll up key insights on a weekly or monthly basis into simple, easy-to-consume formats.
  • Publish sales team feedback to an internal messaging system (i.e., Slack) as it's received.
  • Embed buyer survey responses and/or interview transcripts directly into your CRM Opportunity objects, so they can be accessed easily by the sales team.
  • Alert the product team each time product-related keywords (i.e., a product feature) or decision drivers surface.
  • Compile data about specific competitors into robust battlecards for your sales team to use.
  • Notify sales leaders each time an opportunity receives feedback so they can coach their team.
  • Hold internal debriefs or post-mortems with relevant stakeholders about key lost opportunities.
  • Alert the marketing team about significant wins so that they can pursue more formal case studies.

In general, try to automate the delivery of insights to the stakeholders that helped design your program. Reflect on the challenges they’re facing and the insights they hope to glean from the program to develop strategies for effectively sharing the feedback with them.

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

Many organizations choose to outsource the day-to-day management of their win-loss program to an experienced third-party. Roger Alison of The Pragmatic Institute said:

The odds are stacked against most organizations that are trying to internally conduct [win-loss] interviews. Several tendencies contribute to this problem: difficulty in achieving objectivity; inaccuracy of self-diagnosis; lack of continuity metrics; discretionary priorities of conducting win-loss analysis … if the task is too daunting for an organization, then it must be outsourced.

The top 6 reasons organizations cite for outsourcing win-loss analysis include:

  • Expertise. Dedicated providers, like Clozd, offer skilled practitioners and interviewers who know how to scope and execute effective win-loss programs.
  • Bandwidth. Win-loss analysis can be a full-time job, and few organizations/teams have enough bandwidth to effectively manage their program on an ongoing basis, especially when it comes to conducting frequent win-loss interviews.
  • Internal Adoption. Non-sponsoring teams and individuals are more likely to embrace and implement feedback, especially critical feedback, when they know that the source is an objective and qualified third-party.
  • Confirmation Bias. No employee, regardless of role or experience, can be truly objective in conducting and interpreting win-loss interviews for their own organization due to confirmation bias.
  • Buyer Candor. Buyers are more candid and forthcoming when speaking with an objective third-party. If speaking with an employee, buyers often withhold critical feedback or overstate positive feedback.
  • Longevity & Scalability. Partnering with a dedicated provider ensures program scalability and longevity. Employee-led programs often fail due to lack of bandwidth, competing priorities, employee turnover, etc.

Additionally, providers like Clozd also offer unique software tools to integrate with your CRM and automate the win-loss process. To learn more, request a demo of the Clozd platform here.

ROI & Benefits

Building a business case for win-loss analysis? Companies that conduct effective win-loss analysis achieve meaningful business outcomes. This section explores the benefits and potential ROI of an investment in win-loss analysis.

What are the benefits of win-loss analysis?

The purpose of win-loss analysis is to help a company understand why they are winning or losing sales opportunities. These insights, when current and accurate, directly impact an organization's ability to increase win rates and sales revenue.

In a recent study on win-loss analysis, the 5 most common benefits experienced by companies that practice win-loss analysis included:

  • Improved sales performance (53%).
  • Captured market or competitive intelligence (51%).
  • Improved product strategy or development (51%).
  • Improved marketing content and/or messaging (42%).
  • Improved executive strategy or alignment (38%). 

It is also worth noting that 74% of respondents experienced two or more of the benefits listed above. To see the full study, download a free copy of The State of Win-Loss Analysis Report here.

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

Companies that invest in rigorous win-loss analysis always achieve a measurable return on their investment. Respected firms, including Gartner and Aberdeen Group, have studied and confirmed how win-loss analysis enables higher sales win rates. Todd Berkowitz, Research Vice President at Gartner reported:

A formal and rigorous win-loss analysis program enables better segmentation, product strategy, and sales enablement. Those that take a more comprehensive approach have seen a 15% to 30% increase in revenue and up to 50% improvement in win rates. 

Thus, the best method for estimating the ROI of win-loss analysis is to focus on the potential improvements to win rate. Consider, for example, a company with $10 million in quarterly sales bookings and a historical win rate of 20%. A small win rate improvement of just 10% (from 20% to 22%) would result in additional bookings of $200,000 per quarter. Thus, the annual ROI from their win-loss investment would be at least $800,000 minus the cost of the program. 

For a more comprehensive estimate, use customer lifetime value (LTV) in your calculation instead of just initial bookings. This approach considers all the revenue that will likely come from each client over the life of their relationship with your company. For example, assume the company above has an average deal size of $50,000, but that the average customer LTV is actually $200,000. That means the improvement from 20% to 22% in win rate will drive an ROI of at least $3,200,000.

Other ways that win-loss analysis drives a return on investment include:

  • Decreasing the average ramp time for new sales hires.
  • Limiting the frequency and scale of product development misses.
  • Decreasing time to market for crucial product enhancements or fixes.
  • Surfacing lost opportunities that are actually still in play.
  • Increasing client satisfaction and retention rates.
  • Surfacing win-back opportunities (lost prospects with buyer’s remorse).

How much money do companies typically spend on win-loss analysis?

In a recent study on win-loss analysis, companies reported the following figures regarding how much they spend annually on win-loss analysis:

  • Less than $10,000 per year: 53.6%
  • Between $10,000 and $49,999 per year: 25.2%
  • Between $50,000 and $99,999 per year: 12.6%
  • Between $100,000 and $499,999 per year: 6.6%
  • More than $500,000 per year: 1.98%

The vast majority of these companies (98.7%) intend to maintain or increase their investment.

It's also important to note that the majority of companies that reported a significant return on investment were spending at least $10,000 per year. In contrast, companies that reported no return on investment spend less than $10,000 per year 94.4% of the time. This shows that there is a minimal level of investment required to achieve a return on investment with win-loss analysis. Positive results are achieved once there has been an adequate level of investment. For more insights like these, download a free copy of The State of Win-Loss Analysis report here.

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

The value of rigorous win-loss analysis is tangible and measurable. Monitoring the success of the program can be the most exciting and rewarding part of the initiative. As you analyze win and loss reasons over time, watch for drivers that are trending in a positive direction. You’ll know you have achieved a major milestone if a driver that was once consistently negative evolves into a strength.

Pay special attention to drivers that are points of emphasis for executives and leaders. Watch to see if the programs and tactics they implement end up having a positive impact on the data over time. In this way, win-loss analysis will become a valuable feedback loop that validates successful initiatives.

To measure the ROI of your win-loss investment, you will need to apply one or both of the following methods:

  • Win Rate Method: Monitor your sales win rate over time for segments of your pipeline that are covered by your win-loss program. As your win rate improves, use pipeline data, such as average deal size, to estimate the impact of the win rate improvement. According to a study by CSO insights, companies that implement win-loss analysis achieve an average increase of 14.2% to their win rates.
  • Deal Attribution Method: For sales-led programs, it may be possible to track attribution of specific opportunities for which the outcome was heavily influenced by the win-loss program. For example, a company may learn through a win-loss review that a specific lost opportunity is actually still in play. Or, the sales team may learn that the contact at a lost opportunity is feeling buyer’s remorse and wants to reevaluate their decision. Winning these deals could be attributed to the program. For many companies with large average deal sizes, a single incremental win can recoup the entire cost of the win-loss program.

For a more robust explanation of the ROI and benefits of a win-loss program, and how to measure the success of your program, download a free copy of The Definitive Guide to Win-Loss Analysis here.

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