Beyond the checkbox
What to Really Look for in a
Win-Loss Analysis Service Provider
In the crowded arena of B2B tech, understanding why you win or lose deals isn’t just a “nice to have” anymore—it’s oxygen for your revenue engine. Yet most companies are still making critical strategic decisions based on incomplete, and often flat-out wrong, information.
After over a decade of conducting win-loss interviews for companies ranging from scrappy startups to Fortune 500 giants, I’ve seen firsthand how the right insights can transform a struggling sales operation into a market leader. I’ve also seen how the wrong approach can leave you with pretty dashboards full of useless data.
With Gartner recently releasing their 2025 Market Guide for Win-Loss Analysis Solutions, now’s the perfect time to cut through the noise and focus on what actually matters when choosing a partner to uncover your market blindspots.
The Hard Truth About Your CRM Data
Let’s start with a reality check: up to 75% of the win-loss data in your CRM is wrong.
I know that sounds like an exaggeration. It’s not.
When we dig into the actual reasons deals are won or lost through third-party interviews, we consistently find that the “official” reasons recorded in CRMs bear little resemblance to reality. One client discovered their losses to a supposed arch-rival were overstated by 100%, and their CRM was wrong about two-thirds of the time regarding both who won the deals and why they were lost.
Why such a disconnect? Simple human nature. Sales reps aren’t paid to look in the rearview mirror and assess what went wrong. They’re incentivized to move forward to the next opportunity. And when they do record loss reasons, they’re much more likely to point to external factors (price, features, competition) than their own approach.
This is precisely why third-party analysis is so valuable—and why choosing the right partner matters so much.
Five Essential Qualities in a Win-Loss Analysis Partner
If you’re evaluating win-loss analysis providers, here’s what should top your checklist:
They Get People to Open Up (Really Open Up)
The best insights come from genuine conversations, not formulaic surveys. Look for a partner with a proven track record of getting people on the phone and keeping them there. Our clients often describe this as our “superpower”—the ability to turn reluctant prospects into enthusiastic participants who provide candid feedback.
A good conversion rate from target list to completed conversation should be at least 30%, with top-performing firms hitting 80% or higher for some client types. Without this, you’re getting a skewed sample that tells you little about your actual market.
What’s even more telling: look at the depth of those conversations. Are they getting quick, surface-level answers, or are they uncovering the emotional and political factors that often drive B2B buying decisions?
Thirdside’s “superpower“—the ability to turn reluctant prospects into enthusiastic participants who provide candid feedback.
They Cover the Full Customer Lifecycle
Many win-loss providers focus exclusively on closed deals—won or lost. But that approach misses crucial parts of the story.
The most valuable insights often come from the “no decisions” and stalled opportunities that linger in your pipeline. These zombie deals can reveal messaging problems, qualification issues, or competitive blind spots that wouldn’t surface in standard win-loss interviews.
Furthermore, the best providers connect pre-sale insights (why you win or lose) with post-sale experiences (why customers stay, expand, or leave). This unified approach helps you see the entire revenue cycle in one framework, preventing the all-too-common scenario where you fix your sales problems only to create retention problems down the line.
The best providers connect pre-sale insights (why you win or lose) with post-sale experiences (why customers stay, expand, or leave).
They Focus on Actionable Insights, Not Just Data
Charts and graphs are nice, but they don’t close deals. The right partner should provide not just findings but clear action plans for each stakeholder group in your organization.
One approach I’ve found particularly effective is what we call the “WTF method”—What’s The Fix? At the end of every interview, we ask participants exactly what could have changed the outcome. This gives clients a precise roadmap of improvements, not vague generalizations.
Ask potential providers to show you sample reports and dashboards. Do they show you exactly what was said, by whom, and what to do about it? Or do they just give you aggregated statistics that mask the nuances of individual decisions?
“WTF Method”
(What’s The Fix?) At the end of every interview, we ask participants exactly what could have changed the outcome.
They Understand Business Context, Not Just Research Methods
The best win-loss insights come from interviewers who understand the business realities behind the questions they’re asking. Look for a team with actual experience in sales, marketing, and product roles—people who’ve carried quotas, launched products, and built messaging frameworks themselves.
Career researchers without business experience often miss crucial follow-up questions or fail to recognize industry-specific dynamics that influence buying decisions. They might collect data accurately but miss the story behind the numbers.
Career researchers without business experience often miss crucial follow-up questions or fail to recognize industry-specific dynamics that influence buying decisions.
They Elevate Your Brand, Not Just Collect Data
A surprising benefit of quality win-loss analysis: it can actually improve your brand perception, even among customers who didn’t buy from you.
We regularly hear feedback like: “I commend them for conducting market research. This approach isn’t something I’ve seen many companies do, but it’s impressive. What they have you doing demonstrates the type of company they aspire to be.”
When done right, the very act of seeking feedback shows customers and prospects that you care about their perspective and are committed to improvement. This can even resurrect opportunities you thought were dead.
A surprising benefit of quality win-loss analysis: it can actually improve your brand perception, even among customers who didn’t buy from you.
Red Flags to Watch For
Just as important as what to look for is what to avoid:
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- Unrealistic of Conversion Rate Promises: The rate at which targets will agree to an interview will be determined by many factors including the quality of your CRM data, company industry, contact department, contact seniority, seasonality and more. A provider simply cannot commit to a specific conversion rate, especially a high one. Thirdside consistently achieves a range of a high of 80% to a low of 30%.
- Over-reliance on surveys: Surveys have their place, but they rarely deliver the depth of insight that comes from actual conversations. If a provider leads with surveys rather than interviews, proceed with caution.
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- A focus on quantity over quality: Some providers boast about how many data points they collect, but quantity isn’t the same as quality. Ten in-depth conversations often yield more actionable insights than hundreds of survey responses.
- One-size-fits-all interview guides: Your business has unique challenges and opportunities. If a provider isn’t customizing their approach to your specific market and situation, you’re missing valuable insights.
- Failure to connect insights to action: Beautiful dashboards are worthless if they don’t drive meaningful change. Your provider should be obsessed with how you’ll actually use the insights they uncover.
The Real ROI of Getting This Right
The return on investment from quality win-loss analysis goes far beyond improving sales performance. When done right, it informs nearly every aspect of your go-to-market strategy:
Product teams
that learn which features actually matter to buyers (often different from what they assumed)
Marketing
who discovers messaging that genuinely resonates with target audiences
Sales enablement
that can identify specific training needs and competitive positioning
Customer success
gains early warning signs of potential churn
Executive teams
that can make more informed and strategic decisions
One client we worked with discovered that their complex pricing model—not their price point—was driving away prospects who couldn’t forecast costs beyond year one. With this insight, they transformed pricing from their biggest weakness to a key differentiator.
Another found that their sales teams were overwhelming prospects with too many experts in pitch meetings—what was intended to demonstrate depth of expertise came across as bureaucratic and inefficient.
These aren’t the kinds of insights you get from checking boxes. They come from deep, thoughtful exploration of the human factors driving complex B2B purchases.