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.

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?

‍Competitors

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?

‍Conclusion

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.

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:

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• 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.

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.

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Tactics for sharing win-loss insight effectively include:

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• 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.

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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.

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:

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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.

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

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• 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.

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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.

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.

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).

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.

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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