What If Everything You Know About Why You Win and Lose Is Wrong?

Your CRM may be lying, your AEs are likely guessing, and your lost deals hold the answers. Here's how to uncover the truth.

Imagine playing poker but only reviewing the hands you won. You’d feel pretty good—maybe even confident in your strategy. But without analyzing the losses, you’re missing half the picture. That’s exactly what happens when companies rely solely on their AEs' CRM inputs for win/loss data. The result? A false sense of confidence and a lot of revenue left on the table.

Win/loss analysis helps you understand the steps prospects and customers took during the buying process and why they ultimately made the purchase decision they did. And while every CRM I have worked in over the past 25+ years includes a required loss reason on the opportunity record, data from Anova Consulting estimates that a staggering 60% of sales reps are partially or completely wrong about why they lost a deal. Why? Bias, limited visibility, and lack of time. AEs often cobble together loss reasons from a demo, a few casual conversations, or a last-minute email from the buyer. They're sprinting to hit quota—and that's what you want them to do. But guessing why they won or lost? That requires nuanced conversations about messaging, competitors, product fit, timing, and internal politics—conversations your AEs don't have time for.

Win/Loss Analysis: The Missing Piece in Your Sales Strategy

Win/loss analysis is like GPS for B2B companies, especially those navigating long or complex sales cycles. Without it, you’re driving blind and hoping to stumble upon revenue growth. Here is why I believe win/loss analysis is the missing piece of your sales strategy:

1. Win/loss analysis uncovers the real reason why you win and lose deals. If you look at any CRM, you will likely see reasons like “not a good fit,” “pricing,” or “timing",” but a structured win/loss program often reveals the deeper reasons like missing functionality, competitive differentiation, or messaging misses. All of these insights help refine both the product and your pitch.

2. Win/loss analysis improves sales effectiveness. It’s not just about knowing why you lost, it’s also about why you won. Which value propositions resonated most with your buyers? What sales tactics worked? What objections consistently arise? Armed with these insights, your sales team can double down on what’s working and fix what isn’t, increasing close rates and shortening sales cycles.

3. Win/loss analysis strengthens competitive positioning. In B2B, competition is fierce. Win/loss analysis helps you see where you outperform competitors and where they are eating your lunch. This information allows you to refine your competitive messaging and build better battle cards.

4. Win/loss analysis enhances product development. If you’re consistently losing deals because a key feature is missing, that’s an important signal to your product team. Win/loss data can help guide product roadmaps, ensuring you’re building what the market actually needs, not just what you think it needs.

5. Win/loss analysis helps align your sales, marketing, and product teams. When these teams all operate in a silo, chaos reigns. Win/loss analysis acts as yet another way to bring your teams together a drive alignment (read my other GTM alignment article here). Marketing sees which messages and programs land or flop. Sales gets clarity on buyer objections and motivations. Product learns what features are deal-breakers. This alignment drives smarter GTM strategies.

6. And finally, win/loss analysis boosts revenue and lowers CAC. By continuously learning from every deal (won or lost), you’re optimizing the sales process, making every dollar spent on customer acquisition work harder. The result? Higher win rates, lower CAC, and faster growth. And that’s a combination we can all get behind.

With a clear view of why you win and lose, you understand what’s working, what’s not, and how to improve.

Who Owns Win/Loss Analysis?

Product marketing should own win/loss analysis. Sales-led analysis risks incomplete feedback due to bias or buyers fearing that having a conversation will restart the sales process. Product teams can manage it but need to ask beyond product-specific questions. Since product marketing acts as the connective tissue between sales, product, and marketing, this is the perfect program for them to own from top to bottom (strategy/execution/results/changes). No product marketer? Your CMO should own it as win/loss analysis is a critical input in the go-to-market strategy.

How to Build a Win/Loss Program That Works

Irrespective of who delivers your program (internal or outsourced), your program should cover the same basics:

• Define Clear Objectives: What do you want to learn from the program? Why are we winning and losing? What do customers value the most in our offering? How do we stack up against competitors? Where can we improve the sales process? Be specific. The more focused you are, the more actionable your insights will be.

• Identify Which Deals to Analyze: Not every deal needs analysis. Focus on high-value deals (both won and lost), competitive losses where you went head-to-head with your closest competitor, deals that stalled or dragged on for an unusually long time, and wins that “felt easy” to find patterns that you can replicate. Aim for a sample size of responses that will provide statistically significant results.

• Build the Interview Process: Remember, sales should be selling and not doing these interviews. Use product marketing or a neutral third party. Timing for interviews should be within 30 days of the deal’s close, and a 30-minute phone or Zoom interview works best. You want someone with enough knowledge about the company, product, and/or service that they can dive deeper as needed based on the feedback provided. And finally, a small incentive always helps. I always do a personalized thank-you card with a Starbucks gift card.

• Develop a Standardized questionnaire: Keep your questionnaire structured but flexible. “What problem were you trying to solve when you started looking for a solution?” “What factors influenced your decision?” “What did you like/dislike about our product/team/process?” “Which competitors did you consider/Why?” “What could have been done differently to win your business?” “What stood out positively during your interactions with us?” I recommend mixing open-ended and multiple-choice questions for depth and consistency.

• Capture & Analyze the Data: Collect all interviews and data in one centralized location. Look for recurring themes, common competitor mentions, patterns in buyer objections, and feedback on pricing, the product, and the sales process. You can use HubSpot, Salesforce, or even a spreadsheet to track this.

• Share Your Findings: No one benefits if your analysis gathers dust. Build a feedback loop that includes monthly dashboards for core audiences (leadership, sales, marketing, product, and customer success). Develop quarterly deep dives with those same teams. Hold sales enablement sessions with your sales teams to adjust messaging, rework and train for demos, and competitive positioning.

• Close the Loop with Action: Insights without action are just noise. Once you identify trends, refine your sales playbook and training. Update your competitive battle cards and adjust your pricing strategies as needed. Rework or accelerate campaigns or other marketing programs. And make sure the product development team has all of the feedback for their product priorities.

In-House or Outsourced? Getting the Most Honest Win/Loss Data

Timely feedback is crucial. Reaching out within 30 days of a lost deal yields better insights than waiting months. If you don’t have internal bandwidth, outsource. Vendors manage the process, conduct interviews, and provide insights through dashboards and reports. They often get more honest feedback than internal teams. When I look at internal vs external win/loss analysis it comes down to one thing: if we’re executing the program internally, is there one person on the team that can devote 100 percent of their time to this program? If not, outsourcing is the better option.

I’ve worked with different firms and they all provide roughly the same program. Some provide access to real-time dashboards, interview notes and recordings, and recommendations. Others batch. My preference is for real-time access and this is extremely important if your GTM motion is high-velocity. In a high-velocity motion, having this real-time feedback allows you to quickly pivot to adjust as needed or take advantage of opportunities.

I mentioned above that outsourced providers sometimes get better information from the buyer and this is something you should think about. The buyer has made a purchase decision that they are happy with. We want to ask questions simply to get feedback. If they are providing this information to an employee of the company they just declined, you might not get the whole story. Nobody wants to share bad feedback, nitpick the process or messaging, or talk about why a competitor’s AE was able to build a stronger relationship with the prospect with a person they didn’t select. But they will with a neutral third party.

Stop Guessing. Start Winning.

Win/loss analysis isn’t just a nice-to-have—it’s your unfair advantage. The companies that take a structured, data-driven approach to understanding why they win and lose don’t just improve sales; they sharpen their messaging, outmaneuver competitors, and accelerate growth.

If you’re still relying on gut feel and CRM inputs, it’s time to change that. Build a program, get the real insights, and put them to work. And if you want to assess or optimize your win/loss program, let’s talk—I can help.

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