Every sales team talks about wins and losses, but understanding why a deal was won or lost isn’t as simple as counting results. You might hear guesses in the hallway, or a salesperson could say, “It was price,” but that’s just the surface. If you want to figure out what’s actually going on—how buyers make up their minds and what your teams are getting right or missing—running a win-loss analysis is about the most concrete step you can take.
Here’s what that actually looks like, step by step, with plenty of real-world examples and tips to make the process less of a headache.
What Is Win-Loss Analysis and Why Bother?
Win-loss analysis is a fancy way of saying: “Let’s figure out why customers chose us, and just as importantly, why they didn’t.” It goes beyond intuition or someone’s opinion. You look at actual deals, ask the people involved, and try to spot patterns.
If you’re a sales manager, a marketer, or even on the product side, regular win-loss work is a way to get honest feedback from the outside. It’s used by companies that want to adjust what they’re doing before things go off track.
You don’t need a massive team or a huge budget to do this. The process is about making structured choices, looking at specific data, and asking better questions.
Be Clear on What You Want to Learn
Like a lot of projects, the quality of win-loss analysis hinges on knowing what you actually want to get out of it. The goal isn’t just to collect reasons; it’s to find insight you can act on.
So, ask yourself: Are you trying to figure out if pricing is too high? Are you wondering if competitors are winning on features you don’t offer? Maybe you think your sales process takes too long and that’s hurting your odds.
Write your main questions down. Not two dozen, just three to five key things. Examples: “Did leads drop out because of our demo process?” or “Are we losing to the same three competitors every quarter?”
This helps narrow your focus and shapes who you talk to, what you ask, and what you’ll look for in the results.
Choosing Which Deals to Study
You can’t look at every single deal, especially if your business is busy. But picking only the biggest wins or losses won’t give a fair picture either.
The trick is to look at a cross-section. Include deals that closed, but also the ones that got away. Throw in some that stalled out for a long time, or ended in a “no decision.” Larger companies often aim for a set percentage—maybe 10% of deals each quarter.
Don’t just focus on customers you already know well. Sometimes the best feedback comes from prospects who walked away or those who ghosted your team halfway through the process.
Gathering the Data: What to Look For and Where
Your CRM system is going to be your best friend here. It’s got details on deal sizes, decision timelines, the steps your team took, and which competitors were mentioned. You’ll want to pull reports with as much clean data as you can get—think deal origin, sales reps involved, key activities, and lost reason fields.
But don’t stop at what’s in your software. Teams often track helpful details outside the CRM, like emails, meeting notes, or handover memos. Pulling in this extra context makes the next steps much more reliable.
Some companies use surveys, but the truth is that most of the rich information comes from talking to real people.
Interviewing the Right People
This is the heart of a good win-loss analysis. You sit down—virtually or in-person—and ask people why they made the call. Often, it means talking to former prospects who said “no,” not just the ones who signed up.
It’s tough to get people to take your call when they’ve already moved on. But you’d be surprised—if you’re polite and explain you want feedback, you’ll get responses. You can also offer a small thank-you, like a digital coffee card.
It’s also important to hit up your internal folks. Sales reps who handled the deals will recall things the CRM doesn’t show, like if a competitor offered huge discounts, or if the customer worried about migration trouble.
Getting Useful Answers: The Art of Asking Questions
Don’t just ask, “So, why didn’t you buy?” That’s too broad. The more specific your questions, the more real substance you’ll pull out.
Try things like, “What made you choose the competitor?” or “Was there a feature or promise that swayed your decision?” Ask about each step, not just the final decision—“Was there a point you felt anxious or lost interest in the process?”
If they mention competitors, dig a little deeper. “What did you like about the other offer?” or “How did their communication feel different?” Be curious, but never pushy. You’re not trying to win them back on the spot—just to learn what happened.
Record or take notes (with permission). These little story details are where the gold is.
Making Sense of What You Hear and See
At this stage, you’re piecing together comments from interviews, notes from your CRM, and written survey responses (if you run those). It’s less about building a spreadsheet and more about spotting repetition.
For instance, maybe five out of eight lost deals this month say the same thing—“Your proposal took too long.” Or maybe prospects keep mentioning another vendor’s mobile app that’s much easier to use.
Try grouping the feedback into buckets: product issues, pricing challenges, process holdups, or even personality clashes. Patterns show up fast, especially if you read the quotes back-to-back.
To check your gut, compare what you find to public industry reports or benchmark data. There’s real value in seeing where you stand against companies selling similar things.
What Buyers Are Really Saying: Reading Between the Lines
Sometimes, buyers give you straight feedback: “It was too expensive.” Other times, you need to interpret what’s underneath. Maybe they say, “We went with the bigger name,” but later mention concerns about your implementation support.
This is where you match buyer feedback to your team’s experience. Did your sales rep feel the deal was lost at the negotiation step? Does the buyer mention confusion about onboarding? Piecing both sides together gives a more complete picture.
It’s also worth spotting where your team did something right, not just where things went sideways. For example, maybe all your wins mention they loved how the sales rep checked in promptly each time.
Turning Analysis Into Clear Steps
At some point, the data isn’t helpful if it just sits in a file. The next move is to turn your findings into simple, practical ideas.
Let’s say you notice lots of prospects drop out after demos. You might decide to shorten the demo or start sending demo recordings first. Or if pricing keeps coming up, maybe you run a test with new bundles or discounts.
Don’t try to fix everything at once. Focus on one or two actions you can start this quarter. Translate feedback into ideas the team can see and measure.
Rolling Out Changes and Sharing with the Team
Now it’s time to actually move—share what you found with everyone who touches your deals. Don’t just send a PDF and hope it gets read. Host a quick meeting with an open Q&A, or make a quick video summary.
If you discover your proposals are taking too long, bring in your operations team. If buyers complain that communication drops after the first meeting, brainstorm with sales to draft a simple follow-up checklist.
There’s a lot of value in a regular rhythm. Even something as simple as reviewing new findings in your monthly sales meeting keeps everyone honest and focused on what matters to buyers.
At some organizations, sharing stories from the win-loss process can help teams learn faster. For more on how improvement loops and feedback cycles work in other industries, see case studies and articles over at mod70-europeantour.com.
Keep It Going: How to Make Win-Loss Analysis Part of the Routine
Real change happens when win-loss analysis isn’t just a one-time project. Try scheduling a review once a quarter or after every big product launch.
Go back to your original questions: Have things changed? Is pricing still a concern? Did new features help your win rate? Adjust your focus as you learn more—you might find new patterns or realize old ones no longer matter.
It’s fine to start with small samples and expand as you get comfortable. Even a handful of good interviews once per quarter beats running blind all year.
Wrapping Up
Win-loss analysis doesn’t have to be complicated, but it does take intention. It’s about finding out what’s really happening—and looking at both wins and losses with the same honest eye.
Teams that make time for this work tend to course-correct sooner, waste less effort, and build better products and pitches. If you haven’t started yet, you can always gather a few recent deals and give it a go.
If nothing else, you’ll walk away with a sharper sense of what your buyers care about right now. For most teams, that’s a good enough reason to keep the practice going.