Your CRM data is broken.
According to Shannon Izquierdo, founder of The Prompt Insight Group, research from Pragmatic Institute reveals a startling truth: 85% of information in CRM systems isn't accurate. Even worse, 65% of the time, the competitors tagged in your system are wrong. If you're relying on this data to understand why you're winning or losing deals, you're building your strategy on quicksand.
But there's a solution. Shannon has developed a proven six-step framework for strategic win-loss analysis that transforms unreliable data into actionable insights. In this article, we'll break down her approach and show you how to implement a win-loss program that actually drives results.
Most companies think they're doing win-loss analysis when they review CRM notes after deals close. The reality? Your sellers aren't spending quality time on their notes because they're focused on the next deal. They're logging the bare minimum to satisfy management requirements, not capturing the nuanced reasons why prospects chose you or went with a competitor.
This creates a fundamental problem: you can't build an effective sales strategy on incomplete or inaccurate information. You need to understand where you failed to give prospects confidence that you could accomplish what they needed. And that requires a completely different approach to gathering and analyzing win-loss data.
Shannon is clear about this: start by securing commitment from senior leadership before launching any win-loss initiative. Without executive buy-in, your insights will sit in reports that nobody acts on, and your program will eventually fade away.
How to get buy-in:
Shannon emphasizes that this isn't just about getting permission to run interviews. It's about ensuring that when you identify critical issues, the organization has committed to addressing them. Executive sponsorship means someone with authority is championing the program and holding teams accountable for implementing changes.
Here's where Shannon's approach gets sophisticated. She calls it "triangulation," and it's based on a simple truth: prospects won't tell you the brutal truth directly. When you ask someone why they didn't choose you, they'll give you a polite, sanitized version of events. But when you combine multiple data sources, you start to see the real story.
Shannon's triangulation method includes:
Shannon points out that you'll get twice as accurate information when you use third parties for interviews. Prospects are more honest with an objective interviewer who isn't tied to your company. They'll share concerns about your sales rep's approach, doubts about your product capabilities, or frustrations with your pricing that they'd never mention directly to your team.
This multi-source approach also helps you validate findings. If call recordings show your reps struggling to articulate value in a certain area, and third-party interviews confirm prospects didn't understand your differentiation, you've identified a real problem that needs addressing.
Once you're gathering quality data, you need a system to organize it. Shannon recommends categorizing every piece of feedback into clear buckets so you can take action on what matters most:
Enablement - Sales team behavior and performance
Product - Features and functionality gaps
Marketing - Messaging and positioning issues
Pricing - Cost and value perception problems
Process - Legal and deal structure friction
This categorization is critical because it determines who needs to act on each insight. If prospects consistently mention they don't understand your value proposition compared to competitors, that's a marketing and enablement issue. If they love your product but your pricing structure is too complex, that's a process problem that finance and sales operations need to solve together.
The goal is to move beyond vague insights like "we need to communicate better" to specific, actionable feedback like "our sellers aren't positioning our automation capabilities effectively with CFO personas, and we need new battle cards and role-specific training."
Here's where many win-loss programs fail. You gather great insights, create reports, and then nothing changes. Shannon's framework prevents this by building cross-functional accountability into the process from day one.
To prevent insights from sitting in reports that nobody acts on:
Shannon stresses that this isn't just about sharing information. It's about creating a rhythm where teams expect to receive insights, commit to actions, and report back on results. When your VP of Sales knows they'll be asked about progress on enablement initiatives at next month's meeting, things get done.
Shannon has a philosophy that should be tattooed on every sales enablement leader's wall: "Less content, more context." She once turned off 1,500 pieces of content because nobody was using them. The problem wasn't that sellers didn't want resources; it's that they couldn't find the right resource at the right time.
Shannon's approach instead:
The key is making insights actionable. Instead of a 47-slide presentation on competitive positioning, give sellers a one-page battle card that addresses the three objections prospects raised most often in lost deals. Instead of generic discovery questions, provide role-specific questions that surfaced pain points in your winning deals.
And here's Shannon's critical insight: show sellers you didn't randomly update that battle card. Explain that you interviewed 15 prospects who chose competitors, and here's exactly what they said was missing from our conversations. When sellers understand the research behind the resource, they trust it and use it.
This final step is what separates good win-loss programs from great ones. Shannon emphasizes that you need to close the loop by reporting back to leadership and sellers about what changed as a result of the insights.
Report back on three things:
What insights we gathered from win-loss analysis
What actions we took based on those insights
What results we're seeing from the changes
For example: "We interviewed 20 prospects and identified that our demo was too technical for economic buyers. We created a new executive demo track focused on business outcomes. Win rate with VP-level buyers increased 15% over the next quarter."
This builds credibility with your sales team. When sellers see you're not just collecting data but actually improving their ability to win deals, they'll engage with your resources and trust your recommendations. They'll also be more willing to participate in the win-loss process because they see tangible value from it.
Shannon also recommends attending weekly sales meetings with enablement metrics. Show them that only 30% of the team looked at the latest sales play, that one team needs more product training, or that certain messages aren't landing with prospects. This ongoing presence keeps win-loss insights front and center, not something that's reviewed quarterly and forgotten.
Strategic win-loss analysis isn't a research project. It's a revenue growth engine. When you follow Shannon Izquierdo's six-step framework, you transform unreliable CRM data into accurate customer insights. You turn those insights into specific actions across sales, marketing, product, and enablement. And you create accountability that ensures changes actually get implemented and measured.
Start by securing executive sponsorship so your program has the authority to drive change. Use multiple data sources, especially third-party interviews, to get honest feedback. Categorize insights so everyone knows what actions they're responsible for. Build cross-functional review processes that create accountability. Focus on context over content volume when enabling your team. And track and communicate the changes you're making so everyone sees the value of the program.
Remember: 85% of your CRM data is wrong. But with the right win-loss framework, you can gather the accurate insights you need to increase win rates and drive revenue growth. That's the power of doing win-loss analysis right.
In this episode of SellMeThisPen Podcast, Michael and Shannon discuss why most CRM data is unreliable for win-loss analysis, the dangers of making strategic decisions based on inaccurate information, and Shannon's proven six-step framework for gathering actionable customer insights. They cover everything from securing executive sponsorship to using third-party interviews for honest feedback, and how to turn insights into measurable results across your organization.
Shannon Izquierdo is the founder and consultant at The Prompt Insight Group. She's held content, RFP management, and sales enablement roles at major companies like FedEx and Kinaxis. Shannon specializes in turning win-loss analysis and data insights into actionable strategies for sales teams, helping organizations understand why they win or lose deals and what to do about it.
