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Hopes, Hypotheses, Humility: The 3 H’s of a Successful Win Loss Project

Canada is south of Detroit.

There’s nothing you can do with this information, but it’s pretty cool, right?

Sometimes, learning for the sake of learning is perfectly appropriate. But when it comes to the reasons why your sales team is winning some deals and losing others, simply knowing is not enough.

Unless that knowledge is translated into action—i.e., meaningful adjustments to your product and go-to-market strategies—you may as well not acquire it in the first place.

You may be thinking: Cute intro, Conor, but what’s the big deal? As long as I share that knowledge with the people to whom it’s relevant, the necessary changes will follow. Right?

Right—assuming that, prior to the acquisition of that knowledge, you spent time with the people to whom it’s relevant, uncovered their specific goals and perspectives, and secured their commitment to creating a culture of continuous learning.

See, the unpleasant truth is that most win loss projects fail—not because they produce bad insights, but because they lack focus and neglect emotion.

This is why our newest ebook, The 3 H’s of a Successful Win Loss Project, is all about the work you need to do before you conduct interviews. At the core of this pre-interview work are our three H’s:

  • Hopes
  • Hypotheses
  • Humility

In this blog post, we’re going to briefly discuss each of the H’s. But if you’re serious about making your next win loss project a smashing success, you’ll need to download the ebook—which features insights from two seasoned CI leaders as well as your new favorite win loss project brief template.


In order to be actionable, your findings need to be specific.

How do you get specific? You ask your stakeholders what they’re hoping to get out of this exercise.

By the time you’re finished doing discovery with your sales, marketing, and product leaders, your objective will have gone from “Find out why we win some deals and lose others” to “Find out why we struggle to win the business of [insert customer segment] when [insert competitors] are involved.”


Your stakeholders don’t know why you win or why you lose—but their guesses are probably pretty good. And those guesses will prove useful when you’re staring down the barrel of 8-10 hours of dense interview recordings.

In the absence of hypotheses, the qualitative data contained in those recordings will continuously pull you in new directions, tanking the productivity of your analysis.

But when you’ve got specific hypotheses that you can try to either confirm or reject, you’re well-equipped to identify actionable insights in an efficient fashion.


B2B sales reps don’t like losing—and they certainly don’t like admitting that they lost as a result of their own shortcomings.

This is reasonable, but it’s also problematic, as it makes life difficult for you: A loss-averse seller may withhold information as they’re closing a Salesforce opportunity record, and they may also resist the tactical adjustments that your findings justify.

Here’s the good news: When you do all that up-front discovery work with your senior stakeholders, you’ll secure their buy-in—you’ll get them to commit to making this project a success. And in order to carry out that commitment, they’ll need to work with you to create an environment in which everyone feels eager to learn and improve.

You're about to drive lasting change across your company

A successful win loss project is a beautiful thing; it gives everyone—from sellers and marketers to product managers and UX designers—the insights they need to do their jobs more effectively.

To get a complete understanding of the 3 H’s and the role they play in win loss analysis—and, again, a template that you can use to create an ironclad project brief—download your copy of our brand new ebook today.

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Conor Bond
Conor Bond is on the marketing team at Crayon. If, for whatever reason, you were to rip his headphones off his head and put them on yourself, you’d probably hear Weakened Friends or Charli XCX.