Win-Loss Program Workshop: Learn the 7 Key Building Blocks to Success

Win-loss research has always been an important component of an organization’s success, but it is especially critical in today’s marketplace. Across industries, budgets are dropping or being eliminated, buyers are moving between organizations, and pipelines are dwindling as marketing qualified leads dry up. 

These challenges create scarcity, which drives exponentially fiercer competition. Organizations are adopting a no-holds-barred approach to business, so we’re seeing more consolidation, partnerships, incentives, and some downright desperate acts from vendors trying to steal deals from competitors. 

In this environment, accurate, in-depth competitive and buyer intelligence provides a crucial advantage. But most organizations don’t have the in-house resources to consistently monitor the pulse of the marketplace. And those that do make an effort, often rely too heavily on their sales organizations for win-loss insights. 

The truth is that buyers are the ones who really understand what happened, and — importantly — why. 

To help companies explore win-loss research opportunities, I joined Klue founder, Jason Smith, to present an in-depth masterclass on how to structure a successful win-loss program. In my role as VP of Win-loss at Klue and founder of DoubleCheck Research, I have helped develop many win-loss programs. This workshop covers the seven key steps to establishing and launching a successful win-loss program, including helpful tips, templates, and real-world guidance. 

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Step 1: Identify your stakeholders

Knowing your stakeholders allows you to reverse engineer success. Typical stakeholders are the functional leaders within your organization who can benefit from buyer intelligence: product marketing, product management, competitive intelligence, sales enablement, customer success, and senior leadership. 

Step 2: Determine your stakeholders’ learning objectives

What do your stakeholders care about? Interview each of them about what they hope to learn, and what they plan to do with those learnings. From there, you can develop organization-wide questions and use cases to inform your conversation guide.

Step 3: Identify ideal interview candidates

You need to talk to the right people. It’s about quality vs. quantity. Filtering buyers appropriately — by company size, deal size, product, outcome, region, etc. — can make or break your program. 

Step 4: Align your conversation guide with your learning objectives

Since you’ll only have time to ask about twelve to fifteen open-ended questions, you must choose carefully. We review ten question areas with sample questions. 

Step 5: Design your interview recruitment strategy

Recruitment is best when it’s done early and proactively through strong sales relationships. But incentives and quid pro quo strategies also have their place. 

Step 6: Prepare for interviews

It all comes down to the interview. There are four elements to a successful conversation: building rapport, expressing gratitude, easing the candidate’s mind, and confirming the incentive. We also cover the 5 Whys strategy for getting to the real story behind a buyer’s decision.

Step 7: Analyze and share your findings

The end goal is actionable insights for your stakeholders. We cover how we process interviews, create executive summaries, set up a tagging taxonomy, draft learning objective slides, and more.

In this kind of market, there’s no time like the present.

The value of win-loss research is irrefutable, and – as we’ve seen here – the steps to building a successful win-loss program are easy to define. The challenge is that not every organization can support an ongoing program. 

To help, we’ve created a mini program called the QuickStart Program, which is designed to deliver meaningful win-loss insights on an accelerated timeline for a fraction of the cost: 30 days from start to finish. Organizations are using this program to support business case development, test hypotheses and go-to-market messaging, understand strategic churn, and more. 

If you’ve been thinking about how to harness win-loss research to give your organization an edge over the competition, we’re here to help. The masterclass replay is a great place to start, and there are a lot of great case studies, insider stories, and ask-me-anything sessions on the DoubleCheck Research blog

And if you’re ready to learn more about the QuickStart Program, reach out to me at

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