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Every quarter, leadership teams worldwide pore over CRM data and sales notes looking to glean insights about why they’re winning and losing sales deals.
What they’re doing is searching for patterns. Patterns that could improve sales strategy, inform product decisions, and boost win rates. Yet the explanations they encounter always feel frustratingly familiar:
Here’s the reality: understanding why you really win and lose deals requires more than CRM data and sales team hunches.
You need unfiltered feedback straight from your buyers and a system to capture and analyze that feedback.
The solution? Win-loss analysis.
In this guide, we’ll share everything you need to know about building a win-loss program from the ground up.
Plus, here’s a win-loss analysis template you can download and use alongside this guide.
Win-loss analysis is a process that leverages buyer interviews and surveys to help companies understand the reasons behind their successes (wins) and failures (losses) in sales deals.
By looking at both won and lost opportunities – and hearing directly from buyers about the reasons behind these outcomes – win-loss analysis gives you unbiased insights into:
With these insights, you can work to improve your product, refine your messaging, coach your sales team, improve your compete program and ultimately improve your overall win rate.
We interviewed 5 win-loss experts in one month – these were the 6 top insights 👇
It’s not uncommon for companies to think they’re doing win-loss analysis.
But there’s a big difference between tracking basic deal outcomes in a CRM and running a cross-functional program that actually drives change.
To help companies assess their win-loss efforts and chart a path forward, Ryan Sorely, founder of Klue Win-Loss, developed the “Four Stages of Win-Loss Progam Maturity.”
If you’re just getting started, this framework will help you understand where your program stands today and what it takes to reach the next level.
Let’s look at each stage:
If your program is in Stage 1 or 2 of Ryan’s Win-Loss Program Maturity Model (see previous section), you’re probably thinking: “We’re already collecting feedback and using it to make decisions. Isn’t that enough?”
Here’s why those early stages aren’t enough:
1. Your Sales Team Shouldn’t Run Win-Loss
According to Anova Consulting, 60% of sellers are partially or completely wrong about why they lost a deal. And it’s not their fault – a seller’s job is to sell, not conduct win-loss analysis. Every minute they spend on analysis is a minute not spent chasing leads and closing deals. Most reps will (and should) focus on the latter.
2. Your CRM Data Is Probably Misleading
Bad CRM data could be skewing your win-loss analysis. Just look at the numbers:
Most win-loss data gets recorded through dropdown codes that sellers rush to fill out with vague options like “budget”, “no decision”, or “bad timing.” The result? Strategic decisions get based on outdated, half-baked information.
Want to learn more? Check out our deep dive on why CRM data might be leaving you in the dark when it comes to understanding deal dynamics.
3. Buyers Won’t Tell Sales The Truth
Think about it: when was the last time you told a salesperson the real reason you didn’t buy? Buyers often:
Pro Tip: If you want fast-track your program from “Sales-Sourced” to “Action-Oriented,” Klue’s 360° Win-Loss can help:
The result? Skip months of manual work and build a mature program faster.
Now that we’re clear on the fundamentals, let’s get tactical. Here are the seven steps you need to take to stand up a win-loss program at your org.
A win-loss program is only as strong as the organization behind it. Before you start collecting data, you’ll need to secure buy-in with the right people.
To do this, map out what departments at your org interact with your customers and then consider what insights those stakeholders might need most. Chances are:
Your job? Make sure your program addresses these needs from day one. When stakeholders see their priorities reflected in your strategy, they become advocates instead of obstacles.
Let’s discuss how to go about securing buy-in with a few key stakeholders…
Naturally, this is your most important stakeholder to win over. The good news? It’s typically a straightforward pitch.
Think about it – how often does your C-suite get an unfiltered view of why deals are won or lost? Their “single source of truth” is typically whatever makes it up from sanitized CRM data and second-hand sales reports
Our recommendation, start with one simple question: “Do you feel you truly know why we’re winning and losing deals?” The answer is usually no. That’s your opening.
Watch: Hunter breaks down how he presents win-loss insights to Klue’s exec team 👇
Product, Marketing, Sales, and Customer Success leaders need to see direct value. And that means results, results, and more results.
The key to getting their buy-in? Show how win-loss insights will directly impact their metrics and help them hit their goals faster.
Then bake their needs into your program’s design by asking three quick questions:
Your sales team can either be your biggest champion or your main roadblock. Most hear “win-loss” and think “deal inspection.” Here’s how to flip that perception:
The key? Show them it’s not just about sales. The less it feels like a performance review, the more they’ll champion your program.
Your program needs intentionality right from the get-go. To help with this, we recommend defining clear learning objectives for your program and doing so with your stakeholders.
Learning objectives are the specific insights you want to uncover with your program
They should:
For example, let’s say your leadership team is considering a major pricing change.
Your learning objective could be: “understand how pricing impacts buyer decisions across segments”
Here, you’ll want to focus on uncovering:
The key is making your objectives specific and actionable.
While win-loss analysis drives many benefits across your organization, there’s one clear measurable outcome: increasing your win rate.
But to show improvement, you need a baseline. Here are the two metrics that matter most, in our opinion, and how to calculate them.
You can think of this as the fundamental performance metric for your win-loss program. A win rate is a sales metric that measures the percentage of deals closed (won) out of the total number of deals engaged.
For example: If you closed 100 deals last quarter and won 40 of them, your win rate is 40%.
Here’s how you calculate it:
Win Rate = (Number of Won Deals ÷ Total Number of Closed Deals) × 100
Your win-loss ratio gives you a clearer picture of your overall competitive performance. It’s a metric that compares the number of deals won to the number of deals lost, expressed as a ratio.
For example: If you won 40 deals and lost 60, your win-loss ratio is 2:3.
Here’s how you calculate it:
Win-Loss Ratio = Number of Won Deals : Number of Lost Deals
A common question teams ask: “should we do win-loss surveys or interviews?”
The answer? Both. And develop them in tandem.
Here’s why:
While interviews undoubtedly provide the richest feedback, you can’t (and shouldn’t) interview everyone. This is why a dual approach works best.
Let’s break down how you should approach each…
These are online questionnaires that help you collect data at scale. While they don’t provide the same depth as interviews, they let you spot patterns across your entire buyer base and validate insights from your interviews.
Here are some quick tips for getting the most out of your surveys:
1. Add Segmentation Questions: Include questions in your survey that’ll help you segment response data later:
2. Keep It Brief: Seven minutes is your magic number. Any longer and completion rates drop significantly.
3. Automate The Process: Use Klue’s Buyer Pulse to automatically survey buyers and analyze feedback with the help of AI. It will:
To see a full demo of Buyer Pulse, watch the video below👇
These are one-on-one conversations with your buyers that provide rich, unfiltered insights into their decision-making process. While more time-intensive, they give you the deepest understanding of your wins and losses.
Here’s some quick tips on how to run them effectively:
1. Tie Questions to Objectives: Every question should connect back to your learning objectives from Step 2. If a question doesn’t help achieve your goals, skip it.
2. Prepare More Questions Than You Need: Write 20-30 questions, expect to use 10-15. This gives you flexibility to explore valuable threads and ensures you’re prepared for any direction.
3. Time It Right: Schedule 30-minute calls but block an hour for your calendar. Let good conversations run longer.
4. Follow The Energy: When you hit on something insightful, don’t be afraid to go off-script with follow-up questions. Often the best insights come from these deeper explorations.
5. Keep Questions Clear: Focus on one concept per question. Avoid complex, multi-part queries that lead to surface-level answers.
6. Skip What You Know: Don’t waste time asking about the information you already have from your CRM or deal records. Focus on getting new insights.
Pro Tip: If you’ve already been recording your own win-loss interviews, make sure you’re getting the most out of them. Tools like Klue’s Bring Your Own Interviews (BYOI) feature let you upload your recordings directly into the platform. From there, the software automatically transcribes, analyzes, and tags key themes, making it easier than ever to extract actionable insights from your interviews.
To see a full demo of Klue’s BYOI feature, watch the video below👇
Before you dive straight into interviews, we recommend creating a thorough interview guide.
You can think of this as your blueprint for buyer conversations. It’s not a rigid script, but rather a structured framework that ensures you’re gathering insights that map back to your program learning objectives.
Instead of compiling a random list of questions, focus on mapping key topics to your learning goals.
Topics/learning objectives could include:
By the end of this process, you should have a document organized by key topics (all tied to your learning objectives) with 2-5 action-oriented questions under each.
If you’re stuck on what specific questions to ask, we’ve put together a list of 31 best win-loss interview questions for you to check out.
Now that you’re all set-up, it’s time to actually conduct your win-loss interviews.
Most teams start by asking: “How many interviews should we do?”
Here’s the truth – what matters isn’t quantity, but running focused interviews with the right people.
Let’s break down how to do this right:
Getting awe-inspiring insights starts with interviewing the right people. Here’s how to be strategic about your candidate selection:
No matter how well you’ve prepared up to this point, the interviews themselves will be the single biggest factor in determining the success or failure of your win-loss program.
If you want to dive deep into this topic, we interviewed Ryan Sorely (CEO of Klue Win-Loss) about how to nail your first win-loss interview.
In the meantime, here are some key tips to get you started:
You’ve done the interviews. You’ve gathered the feedback. Now comes the make-or-break moment of your win-loss program – turning raw data into usable insights.
This is where many programs stumble. Teams either get overwhelmed by the mountain of data they’ve collected or rush to share disconnected findings that don’t tell a clear story.
Here’s how to analyze your data effectively:
1. Align Data With Your Program’s Learning Objectives
Go through your transcripts and sort feedback based on your original learning objectives.
For example, if your objective was “Understand why enterprise deals choose competitors,” collect all feedback about:
The beauty of a well-structured interview guide? Most answers will already align with your learning objectives and be neatly sorted on key topics.
2. Text Tagging
Even after aligning with objectives, you’ll have lots of unstructured data. Here’s how to organize it for easier analysis.
3. Automate Your Win-Loss Data Analysis
If manually tagging feels overwhelming, tools like Klue’s 360° Win-Loss can do the heavy lifting. Its AI-powered tagging automatically organizes interview data into actionable themes, helping you uncover patterns like win-loss reasons, competitive gaps, and sales performance trends.
You’ve done the hard work of collecting and analyzing your win-loss data. Now you get to share these insights across your organization.
Here are the key ways we recommend presenting your findings:
After each win-loss interview, create a detailed report about the specific deal discussed.
These reports help teams understand exactly what happened in specific deals. They should include:
Pro tip: Always attach the interview recording and transcript to deal reports. Some stakeholders will want to dig deeper.
Let’s face it – executives love their summaries. And for good reason. These presentations help leadership spot patterns across deals and make strategic decisions.
With a win-loss executive summary, you’ll want focus on delivering the most value possible for senior leadership team. So, make sure your presentation emphasizes:
These presentations are perfect for quarterly business reviews and board meetings where you need to tell a clear story about what’s happening in your deals.
Your sales team needs actionable competitive intelligence that they can use in the field. These presentations will be goldmines for this. They also double as perfect for sales kickoffs and coaching sessions.
Start with the wins – show your team what’s working:
Then tackle the challenges:
Pro Tip: take your top insights and build them into your sales battlecards. Turn common objections into proven responses, competitor mentions into comparison points, and buyer pain points into targeted talk tracks. In our experience, win-loss insights offer some of the best primary competitive intel available.
In this highly tactical Compete Week keynote, Hunter breaks down the five different ways he distributes win-loss intelligence at Klue👇
Building a win-loss program takes work. But now you have everything you need to start gathering the insights that will transform your business:
Remember – getting a complete view of your wins and losses isn’t about any single data point. It’s about seeing the full 360-degree picture of why buyers choose you (or don’t).
Good luck!
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