Avoiding False Starts in Your Win-Loss Project

Posted on: October 25, 2022
By: Matthew Reeves

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  • An underwhelming first win-loss presentation can kill the project before it’s had a chance to take off.
  • The most common reason is that leaders don’t know how to action the results they are seeing.
  • We cover how to avoid this trap and maximize the impact the first time.

Everyone is silent and staring back at you with blank expressions. 

Zoom is a sea of cameras-off, muted tiles.

“Any questions?” You ask.


It’s like you’ve asked your dog to order you some nigiri from Uber eats. Vacant stares. Someone is distracted by a leaf.

It’s the telltale sign that your presentation hasn’t landed. If it’s a win-loss project. It’s a good bet it’s about to be shut down. 

Let’s avoid that.

Win-Loss Projects Fail at the first Results Meeting.

The first results session is a make-or-break moment. If leaders get a major “ah ha” moment, it drives interest and action quickly. 

It can feel like a switch has been flipped.

Entire teams can go from rarely speaking to customers to begging for more customer interviews. They want to build their strategy based on customer-feedback (which is what being customer-centric really is). 

But when the results fall flat, delivering the results feels like pushing ideas onto your team.

We’re going to cover how to make sure results don’t flounder. 

The Root Cause is No Clear Path

Here’s something research-based: it’s common for flamingos to stand in water, and the water freezes around their spindly leg and locks them in place. 

It’s totally factual, but very little we can do with it. It’s unusable research. A poor results meeting feels like you’ve just told people that fact. They sit and think to themselves. 

“ok, so what?”

Ensure Leaders See a Path

When leaders can clearly link the results you show them to the action they need to take: you have a killer win-loss research presentation, one that drives changes across the organization quickly.

Let’s see how you can build that. 

The Secret is to Involve Leaders Early

Product Marketers sometimes have the urge to use win-loss to prove that some other teams’ idea is wrong. 

It’s very tempting – I’m pretty sure I’ve done it myself (let’s move on) – but doing so leads to poor results meeting, and that kills the project. 

Great Product Marketers take on a Servant Leadership approach. 

They see the role of win-loss as part of how they provide sales, marketing, and product teams with the information the teams need to excel in their roles.

They don’t:

  • Tell sales how to sell. Instead, they help sales understand what positioning will make more sales.
  • Tell the product team what to build. Instead, they dive deep into the root cause of customer problems so the product team can figure it out. 

Instead, they find out what burning questions teams have and earn their trust by validating their answers with real buyers. It’s the best way to begin win-loss.

Here’s how to do it, step by step. 

Steps to Building Win-Loss Questions Collaboratively

1. Hold a short “Project Goals” meeting.

As early as possible, gather the teams who’ll use win-loss data and explain the goals. Make it clear that win-loss isn’t to prove somebody right or wrong, it’s to take the pulse of real customers and test all of our ideas.

2. Then, Meet the teams 1-on-1, or in Team-Based Groups

It’s common that sales think the product is falling behind, or a product manager thinks sales might not be highlighting the right benefits. If you have alignment issues in your organization, I’d definitely consider meeting separately.

The goal is to get make sure every team is bought into the project.

3. Ask These Questions to Generate Illuminating Questions

First, ask each team member: 

  1. If you could mind-read our customers: what top 5 questions would you ask them? 
  2. What do you predict the answers will be?
  3. What hypotheses do you have for why customers choose not to buy from us? 

Sometimes I set this as homework, and when we meet, I move on to the following set. Sometimes you can cover it all in one session.

Then, once you have a list, ask these: 

  • What would you do or change if you knew the answer? 
  • What would you do if the answer was the opposite of what you predicted?

You can see where I’m going. I want to include at least one question from every team, and the ideal questions are the ones where there is a clear action, whatever the outcome might be. 

Key tip: make sure they know that some questions will be cut. We may have generated 10, but we need the top 1 or 2 for now. We can ask the rest in the future. 

Repeat this for each team.

4. Create the Master Question List

You’ll now have a list of questions each team wants to hear, and you’ll probably have a list of core win-loss questions to ask, too.

With limited time, you’ll likely have a long list and need to prune your complete question list.

When you get into presenting results, it’s much better to present findings of 10 questions people actively wanted to know versus 65 questions they had little interest in.

Be ruthless in your question-culling.

5. Reset Expectations

You’ve taken time with each team but probably culled some of their questions. Now is the time to make sure they are aware of that. 

The way I frame the challenge to people is: We only have 30 minutes with an interviewee. We want to have a conversation with them on a few topics. We want to give them time to really explore a topic. That usually means 8-10 deep-diving questions.  

I’ll show which one I’ve chosen if I’ve had to cut some.

A Great Results Meeting

Fast forward to results time. 

You are delivering a super-focused presentation that hits on the findings of each team’s questions. 

What you’ll find, when you get it right, is instead of muted mics, you’ll be inundated with questions.

  • “Did the customers say anything about our reporting?” 
  • “Did the speed of reply come up?”
  • “Did you get a sense that discounting was an issue”?

Their clarifying questions will stimulate more ideas, questions, and critically: more decisions that result in action. 

But as a facilitator, make sure to ask at the end:

“Does anybody see any changes or actions we should take as a result of this.” 

You’ll probably get some lively ideas. 


Simple in concept, the steps I’ve outlined add time to your setup — one of the reasons it’s so commonly skipped over. 

But, if you want to create a culture where each team listens to what real customers have to say and takes action on the findings, the extra week or so is well worth it. 


  • Research projects underwhelm when leaders can’t see how the research can lead to changes. 
  • Involve your team early. 
  • Prioritizing the questions they have self-identified could drive decisions.
  • Be ruthless and cut questions that don’t drive decisions.
  • Be inundated with the team’s follow-up ideas.
  • Repeat. 

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