The Ultimate 7-Step Guide to Win-Loss Analysis (2024)

Niko Pajkovic

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:

• “Our price was too high”
• “We were missing X features”
• “They went with competitor Y”

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.

What Is Win-Loss Analysis?

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:

• Your product – where it shines and where it falls short.
• Your sales experience – how buyers feel about interactions with your team.
• Your marketing – whether your messaging and campaigns resonate.
• Your buyer’s priorities – what matters most to your customers.
• Your competitive position – how you compare to your competitors. 

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 👇

The Four Stages of Win-Loss Maturity

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:

• Stage 1: Sales-Sourced: Your sales team gathers some buyer feedback, typically via dropdown codes in your CRM. But there’s no formal process, just sporadic insights based on what sales reps remember or choose to share. This leads to incomplete and often biased data.
  
• Stage 2: Siloed: One department runs win-loss analysis, but insights aren’t shared widely across your organization, limiting the potential impact on overall business strategy.
  
• Stage 3: Integrated: You have a dedicated program owner collecting data across all buyer touchpoints. However leadership buy-in may be lacking, and there’s no structured approach to turn those insights into action.
  
• Stage 4: Action-Oriented: A dedicated owner oversees the program, and there’s strong cross-functional alignment and leadership support. Insights are reviewed regularly by key stakeholders, data is collected systematically, and most importantly, specific, measurable actions are taken based on these insights.

Why You Need a Mature Win-Loss Program

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:

• 91% of CRM data is incomplete (Salesforce)
• 70% becomes inaccurate annually (Salesforce)

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:

• Give vague answers to avoid awkward conversations
• Hide their true decision criteria
• Sugarcoat negative feedback

Pro Tip: If you want fast-track your program from “Sales-Sourced” to “Action-Oriented,” Klue’s 360° Win-Loss can help:

• Centralize all buyer insights
• Automate data collection
• Spot patterns with AI
• Share findings instantly

The result? Skip months of manual work and build a mature program faster.

How to Conduct a Win-Loss Analysis in 7 Steps

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.

Step 1. Rally Your Win-Loss Stakeholders (Get Program Buy-In)

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:

• Product is dying to know what features make or break deals
• Marketing is eager for messaging validation data
• Sales leaders are interested in process and execution gaps
• Executives want deep buyer insights to guide big-picture decisions

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…

CEO/C-Suite

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 👇

Functional Leaders

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:

• What do you want to learn from win-loss?
• What would you ask buyers directly?
• How will you use these insights?

Sales Team

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:

• Make it clear this is about improving the whole go-to-market motion
• Show how win-loss insights help close more deals
• Turn win-loss data into competitive insights they can leverage
• Keep their involvement light (just warm buyer introductions)

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.

Step 2. Get Clear On Your Win-Loss Learning Objectives & Strategy

 

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:

• Align with company goals
• Address stakeholder needs
• Drive specific actions
• Be measurable

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:

• How buyers perceive your pricing vs competitors
• Which pricing discussions create friction in deals
• What objections sales struggles to overcome

The key is making your objectives specific and actionable.

Step 3: Calculate Your Win-Rates and Win-Loss Ratio

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. 

Calculating Your Win Rate

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

Calculating Your Win-Loss Ratio

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

Why these metrics matter:

• They provide a clear baseline to measure program success
• They help you set realistic improvement goals
• They make it easy to demonstrate program ROI to stakeholders

Step 4: Create Your Win-Loss Interviews & Surveys

A common question teams ask: “should we do win-loss surveys or interviews?”

The answer? Both. And develop them in tandem.

Here’s why:

• Surveys capture trends at scale
• Interviews give you deep insights

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…

Win-Loss Surveys

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:

• What’s your company size?
• Which region are you based in?
• What’s your estimated annual budget?
• Which product line interests you most?

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:

• Connect directly to your CRM
• Send surveys automatically when deals close
• Get higher response rates than basic survey tools like Google Forms
• Analyze feedback patterns with AI

To see a full demo of Buyer Pulse, watch the video below👇

Win-Loss Interviews

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👇

The Interview Guide

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:

• Business Drivers: What triggered their search? Which problems needed solving?
• Selection Process: How did they go about finding a solution? What was their evaluation process?
• Product Experience: What features mattered most? How well did the product meet their needs?
• Pricing and Packaging: How do they view the pricing structure?What’s their take on overall value?
• Sales Experience: How helpful was the sales team? What could have made the process better?
• Buying Process: Who made the final decision? What approvals were needed?
• Demo Experience: How effective was the demo? What stood out (good or bad)?

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.

Step 5. Conduct Your Interviews

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:

Recruit the Right Win-Loss Interview Candidates

Getting awe-inspiring insights starts with interviewing the right people. Here’s how to be strategic about your candidate selection:

• Align With Learning Objectives: Use your program objectives to qualify candidates in or out.
  
• Create Research Cohorts: Group your candidates by shared characteristics (product line, deal size, region). You need at least 10 similar deals to identify reliable patterns.
  
• Target Late-Stage Deals: Focus on buyers who went deep into your sales process. They’ve seen everything – from demos to pricing – and can provide comprehensive feedback.
  
• Focus on Competitive Deals: Prioritize opportunities where you went head-to-head with specific competitors you want to learn more about.
  
• Go Through Sales: Have your sales team make the intro. They know the right contacts and their warm relationship leads to higher acceptance rates.
  
• Time Your Outreach Right: Contact buyers within 90 days of their decision. Any longer and memories fade; any sooner and you might disrupt active deals.

Getting the Most Out of Your Interviews

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:

• Make It Clear That This Isn’t a Sales Call: Start by letting them know you’re not trying to revive the deal. You’re here to learn.
  
• Pick Your Interviewer Wisely: Get someone who’s impartial, matches your buyer’s seniority level, and keeps their cool under pressure.
  
• Train Those Interviewers: Show them the ropes – from deal research and warm-up chats to keeping the conversation flowing.
  
• Cameras On: You’ll get better insights when you can see each other’s faces.
  

• Master the “Five Whys”: When a buyer shares something important, start asking “why?” Take their answer and ask “why?” again. Keep going until you hit the root cause (usually 4-5 times deep).

Step 6: Analyze Your Win-Loss Data

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:

• Enterprise requirements
• Competitor selections
• Decision criteria
• Deal breakers
• Selection process

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. 

• Identify key quotes from your transcripts
• Assign each quote a main topic and sub-topic
  • Example: “Their product was easier to use than other vendors'”
    • Main tag: Product 
    • Sub tag: Ease of Use

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​.

Step 7: Present Your Findings

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:

Win-Loss Deal Reports 

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:

• A clear “Why We Won/Lost” summary upfront
• Key findings tied to learning objectives
• Direct quotes from the buyer
• Analysis of every deal stage (discovery through decision)

Pro tip: Always attach the interview recording and transcript to deal reports. Some stakeholders will want to dig deeper.

Win-Loss Executive Summaries 

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:

• The biggest, most urgent insights that need attention
• Clear trends emerging across multiple interviews
• Data tied directly to your program’s most important learning objectives

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.

Win-Loss Sales Presentations 

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:

• Most effective sales tactics
• Successful deal strategies to replicate
• Positive buyer feedback on team performance
• Winning competitive positioning

Then tackle the challenges:

• Common objections and how to handle them
• Where deals get stuck in the process
• Competitor mentions

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👇

Time to Get the Full Picture

Building a win-loss program takes work. But now you have everything you need to start gathering the insights that will transform your business:

• A framework to assess your program
• Steps to get stakeholder buy-in
• Tools to gather deep buyer feedback
• Ways to turn insights into action

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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