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Starting and Running a Win/Loss Program

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Win-Loss Program

Win-Loss Program


THE CONCEPT OF WIN/LOSS HAS BECOME MORE WELL-KNOWN and appreciated in the past few years. In a business culture enveloped in data and analytics, win/loss research stands as a formidable partner to executives looking to better their organizations.

Today, with increased adoption, the question is no longer, “Why do we need to do win/loss?” Instead, the question has become, “How do we do win/loss well?”

When conducted well, win/loss delivers long-term results and actionable next steps. However, setting your company up for success must start on day one. Unfortunately, many companies miss the mark. Every organization is different, but there are some common guidelines that should be considered from the onset to maximize the value of your win/loss program.


Do: Assign Clear, Realistic Goals for the Initial Program

Set yourself up for success. Keep the goals for your first win/loss program simple and clear. Instead of trying to accomplish everything at once, consider the following initial objectives:

  • Achieve operational efficiencies. Focus on operationalizing the program before paying attention to how your business metrics are improving. Have goals like “create an efficient, repeatable process for identifying deals to conduct a debrief” that includes things like extracting deal information from your CRM and verifying with the account team that the target contact is the correct respondent. If you’re partnering with a third party who will conduct the interviews, make it a goal to “establish a coordinated process with the partner organization so they know when they can begin reaching out.” Once you complete interviews and have transcripts, be sure to have a central repository where key stakeholders can access the completed interviews. Working out the bugs upfront will help your program in the long run as sample sizes increase.
  • Institutionalize the research. Getting buy-in throughout the organization won’t happen overnight. Share program goals upfront to establish realistic expectations. Be sure to note that short-term goals are to figure out how to run a program (see above operational goals), while long-term goals include using the aggregate data for strategic planning. Also, be sure to communicate to your organization that the program is meant to be a learning and coaching tool, and there’s no reason to be opposed to the feedback. Make it clear that the program isn’t meant to point out people’s mistakes. Be thoughtful about who accesses the initial interviews and encourage those people to read the transcripts with open minds. As more interviews are completed, people will become more accustomed to the research and begin to want more.


Don’t Expect Immediate Results

Expecting win/loss research to immediately deliver transformational insights is a simple way to put unnecessary pressure on the program. The early stages of a win/loss program are about gaining operational efficiencies and trusting that the value of the research will be revealed as time goes on and more feedback is captured. A significant part of win/loss value comes from seeing how results change and improve over time.


Do Begin with a Right-Sized Program, then Expand

Focus your initial program on a specific product, region, or other market segment. Make sure you’re capturing as much feedback as possible about that specific niche before expanding the research. Starting small should also map back to your initial goals. Keeping the size of the program narrow at first allows you to focus on improving processes and efficiencies.


Don’t Boil the Ocean

You likely will face pressure, both internal and external, to build a program that captures feedback across any and all swaths of your company. You will have dreams of seeing how scores for your product demonstration vary across regions, or what prospects who evaluated you against a certain competitor thought of your product’s ease of use. All those capabilities will come, but it will require a large, robust program. If you don’t first get a right-sized program to run successfully, you will never be able to build a large-enough data set to unlock those insights.


Do Find the Right Person to Run the Program

By definition, win/loss focuses on constructive feedback that helps individuals and organizations improve. For a win/loss program to succeed, the face of the program needs to be someone passionate about feedback and improvement. Appoint a person with a growth mindset who constantly asks what they could have done better or seeks reactions to their work—even if it’s unpleasant. This person’s passion and attitude will help the program be perceived as a vehicle for improvement, as opposed to a witch-hunt designed to highlight people’s mistakes.


Don’t Create a Single Point of Failure

Relying on one person to manage a win/loss program leaves an organization with a single point of failure. Even if he or she is a strong champion and has a growth mindset, priorities can shift and the program may be compromised. You don’t want your champion to be a lone wolf. Ensure he or she has people to rely on to support tasks, such as extracting deals from your CRM or coordinating internally with executive stakeholders.


Do Identify Cross-Departmental Stakeholders

Part of the tremendous value of win/loss is its relevance to many different areas throughout an organization. Sales, product, marketing, pricing, research, competitive intelligence, strategy, and finance all can be considered key stakeholders for a program. Ensure these areas have access to transcripts and aim for cross-departmental representation when it’s time to present the program’s findings. This also helps put everyone on the same page. Certain individuals may be more aware of what’s going on related to specific deals (e.g., the head of sales), but not everyone is privy to that information. Bringing together all departments for a read-out of what prospects think of your company is an extremely valuable exercise, as it allows for open discussion and sharing of different perspectives.


Don’t Ignore Sales

A successful win/loss program can’t happen without sales involved. It may work in the short term but is not sustainable. If the program is launched by a department other than sales, make it clear to the sales team that the program is designed to help sharpen their saw and raise their game, not rub their noses in constructive feedback. Otherwise, sales can make it difficult to run a program by blocking deals that should be considered as part of the debrief.


Do Leverage Technology

Win/loss programs have a lot of moving parts: interviews that have been completed, deals that are in the field, contacts who politely ask to do the interview another time, contacts who not-so-politely tell you they never want to be called again. There is a range of tools to help with this process.

In addition to managing the program, there also are demands for real-time analytics. Today’s business climate demands instant access to information, and having strong technology is essential for providing those data points. When starting a win/loss program, think of the role of technology as easing the program management and providing real-time analytical pulse checks. That said, be careful to not overestimate the role software will play in making the program a success.


Don’t Overlook the Human Touch

For all the benefits technology brings to our professional lives, when it comes to win/loss there is still something to be said for human involvement. Consider the process of extracting deals from your CRM to pursue for interviews. This truly is a garbage-in, garbage-out exercise. The companies that automate the entire process spend most of their time pursuing contacts or completing interviews on deals for which there isn’t truly meaningful feedback to be gathered. A better approach is to:

  • Automate the report
  • Filter out deals that don’t meet certain criteria (e.g., revenue size, did not reach a late stage in the sales cycle)
  • Have someone familiar with the remaining deals quickly vet the information to ensure the contact listed can provide meaningful feedback and that the contact information is accurate

Automating the entire process may save time on the front end, but ultimately it leaves you with data and results from which meaningful value can’t be extracted.


Do Deliver Data Back into Your Organization

When it’s time to review win/loss data, you may find yourself or others saying that the findings validate what you already knew. If you’ve been using a third party to run your win/loss program, this is a good thing! Win/loss conducted through a third party captures completely unbiased feedback. It’s data your organization can trust without worrying about internal agendas or respondents’ candor. Having independent validation leads to confident, clearer decision-making.

If you’re conducting win/loss without partnering with a third-party consulting firm, allow the data to speak for itself. Educating stakeholders about the process (i.e., that feedback and data are coming directly from prospects and clients) reinforces the validity of themes pondered or debated before the win/loss program. At this stage, the data and analytics tell the story. Encourage your stakeholders to listen to it.


Don’t Rely on an Online Dashboard to Tell the Whole Story

Just as you shouldn’t rely solely on technology to run the operations of your program, you also shouldn’t think that an online dashboard can replace the value of custom reporting. Having someone with an analytical mind and knowledge of your business read through the interviews and pull trends and insights into an executive report provides more value than any automated report or dashboard. When it’s time to present those findings, make sure your broad group of stakeholders is present and allow time for discussion of their different perspectives. That data-fueled cross-departmental conversation is when the true value of win/loss is unlocked.


Know Your Program Is a Success

As with any business exercise, the spotlight will be on the value the win/loss program returns. Yes, it should help business metrics improve, but don’t restrict the definition of success only to whether your win rates improve.

By following the guidelines outlined here for building a successful win/loss program, your organization will become better at sharing information internally. And as more information is shared, you will see clearer and more confident decision-making. Eventually, you will find that win/loss is part of your company’s DNA as business leaders will crave seeing how aggregate results are trending and individual salespeople or product marketers will ask for transcripts of situations in which they were involved.

When you have built a program that facilitates a culture of learning and improvement at your organization, you will know that your program is a success. From there, the sky’s the limit.



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