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Thursday, April 24, 2025

The Anatomy of an Effective Win/Loss Program

After over 20 years of working with companies to help them implement and build successful win / loss programs, we’ve heard every question under the sun. This series will explore the areas we often get asked about the most.

As with many things in life, “it depends” is a common answer we resort to. Rarely is there a one size that fits all or off-the-shelf blueprint for win / loss program success. However, there are frameworks and things to keep in mind to help you navigate these common areas of curiosity.

Part 1: Getting Executive Buy-In for Win/Loss Analysis

Getting Executive Buy-In is firmly entrenched in the curriculum of “Win / Loss 101”. And yet, it is a step that many organizations try to skip or treat as a check the box exercise. Even for the companies who really understand its importance, there is the question of how to effectively involve senior stakeholders with the program. This blog will explore both why executive buy-in is important, as well as how to get it.

Why Executive Buy-In is Important:

Think of a plane taking off on a cloudy day. Typically, there is some turbulence before the plane reaches its cruising altitude. Similarly, a win / loss program will run more smoothly if it reaches the clearer air space of the highest rungs of an organization.

A win / loss program is a great example of “you get what you put in”. Strong efforts will yield strong results. In a world of competing priorities, knowing that stakeholders are behind the program and are looking for results from it helps to ensure the required levels of attention are paid to the program to ensure success.

Said differently, executive buy-in can be a good carrot. It can also be a good stick to ensure program compliance from sellers to ensure they are not dodging the program or not providing accurate contact information to collect feedback. When an executive makes it known the program is not optional, and the results will not be used as a “witch hunt” but to help the entire organization improve and win more, the raw inputs (buyer contact information) are easier to access.

Executive buy-in also positively impacts the smoothness of other program operations:

• Interview guide design: When designing interview guides, areas of priority for stakeholders can be emphasized
• Analyzing results: When analyzing results, as opposed to boiling the ocean, stakeholder areas of focus can be highlighted
• Getting cross-functional alignment: Getting cross-functional alignment can be made easier through stakeholder involvement
• Increasing response rates: Increasing response rates as customers recognize the importance of providing feedback if asked by an executive

Getting Executive Buy-In

Now the part that has many organizations struggling: truly getting executives to buy-in.

In general, the best way to secure executive support is by aligning the program to their areas of interest. This can be in terms of who you talk to (executives tend to care about the biggest customers, or maybe your organization is rolling out a new product and they want initial feedback from those early adopters) as well as what you talk to them about (head of sales interested in how effective you were at differentiating against the competition? Make sure to ask about that specifically).

Be sure to also tailor your communication to the individual stakeholder you are interfacing with. When talking with sales leaders, emphasize how win / loss can positively impact win rates (Gartner says by up to 50%). When talking to the CMO, highlight how the research will help refine messaging and collect competitive insights. When working with the CEO or head of the business, be sure to note how the program will help ensure strong levels of customer centricity, as well as build strong internal cultures by accentuating values such as a growth mindset and commitment to feedback.