Win-Loss Analysis: A Strategic Guide to Drive Business Growth

How do you really know if your sales strategy is crushing it or quietly losing you deals? 

Losing sucks, but what’s worse? Not having a clue why it’s happening. That’s where Win-Loss Analysis comes in.

If you want your team to stop guessing and start winning more, you’ve got to be pro at conducting win-loss analysis. Let’s start with the basic definition.

What Is Win-Loss Analysis?

A win-loss analysis is reviewing and understanding why sales opportunities are won or lost. It helps sales professionals understand what worked, what didn’t, and what needs to change.

Specifically, it is a structured approach to gathering insights from closed sales opportunities. It examines customer feedback, competitor strategies, and internal sales performance to determine what influenced a deal’s outcome. 

For example, your sales team pitched a software solution to a mid-sized company but didn’t close the deal. 

A win-loss analysis would involve reaching out to the client to understand their decision-making process. Maybe they thought your pricing was too high, or perhaps a competitor offered a feature you didn’t. 

A basic formula for Win Rate and Loss Rate is:

Win Rate (%) = Number of Deals WonTotal Number of Deals X 100 

Loss Rate (%) = Number of Deals LostTotal Number of Deals X 100

When to Conduct Win-Loss Analysis?

So, when should you hit pause on your day-to-day grind and run a win-loss analysis? Simple answer: when your team is consistently missing targets or you’re winning deals but not sure why.

If you don’t know what’s driving your success or failure, it’s like flying blind. For example, if your win rate has been stagnant or, worse, declining, it’s time to investigate. Are your competitors out-pricing you? Are your reps focusing on the wrong prospects? 

You can’t fix what’s broken without knowing what’s wrong, and a win-loss analysis gives you the clarity to move forward with purpose.

Here’s a quick gut check to see if it’s time:

• Are your win rates lower than industry benchmarks?
• Have you lost deals to a competitor more than once in the last quarter?
• Are prospects frequently “ghosting” your sales team after promising conversations?
• Do you suspect price objections are derailing your deals?
• Did you recently launch a product, service, or feature and feel unsure how it’s landing?

If you answered “yes” to even one of these, it’s time to conduct a win-loss analysis.

The right time to conduct it might also be when you’ve launched a new product, entered a new market, or shifted your sales strategy. 

Benefits of Win-Loss Analysis

If a win-loss analysis is conducted correctly, it will give you business insights that will directly impact your bottom line. Let’s break down the key benefits:

Understand Why You’re Winning or Losing Deals

A win-loss analysis helps you figure out precisely what’s driving customer decisions. Maybe your product features are knocking it out of the park, but your onboarding process scares prospects. Or perhaps a competitor is undercutting your pricing.

Sharpen Your Sales Process

Even the best sales processes need fine-tuning. The win-loss analysis highlights areas where your team can improve, such as:

• Product development.
• Follow-up time optimization.
• Weak discovery process failing to uncover key pain points.
• Sales messaging that doesn’t align with prospect needs.
• Ineffective objection handling during critical stages.
• Sales cycles that are too long and lose momentum.
• Unclear or weak value proposition presentation.
• Losing deals to competitors with stronger offerings.

Strengthen Customer Relationships

When you reach out to prospects post-sale—whether you won or lost—you show them you’re listening. That’s a relationship-building moment. Even lost deals can turn into wins later if the customer feels heard and valued.

Keep an Eye on Competitors

Your competition isn’t standing still, and neither should you. The win-loss analysis gives you real-time intel on what your competitors are doing right—and what they’re missing. 

Maybe a competitor is winning deals on price, but their service gets bad reviews. That’s an opportunity to emphasize your value while closing the gap in areas where you’re losing.

While interviewing your potential customers, they might share why they choose your competitors over your business.

Steps to Conduct a Win-Loss Analysis

Step #01: Collect Data

The foundation of a solid Win-Loss Analysis starts with collecting the right data from the right sources. Without reliable data, you’re just guessing. 

Here’s the type of information you should get your hands on:

• Deal Details: Industry, company size, decision-makers involved, and the overall timeline.
• Reason Codes: Document why deals were won or lost (e.g., price, features, timing).
• Customer Feedback: Ask what influenced their decision, what they liked, and where they felt you fell short.
• Competitor Comparison: Find out if a competitor won the deal and why—pricing, features, or relationships.
• Internal Insights: Sales team feedback on challenges, objections, and lessons learned during the process.

You should reach out to the following areas of your company to get insights:

• Sales Reps: They’re on the front lines and have firsthand insights into why deals progressed or stalled. Conduct interviews or surveys to capture their perspective.
• Prospects and Customers: Ask them directly whether you won or lost the deal. Post-decision interviews or surveys are a goldmine for honest feedback. Use Typeform, Google Forms, or SurveyMonkey to collect structured customer feedback. 
• CRM Systems: Analyze deal data from your CRM, such as Salesforce or HubSpot. Look at pipeline stages, deal velocity, and win/loss ratios.
• Competitor Research: Pull in intelligence about competitors from the sales team or tools like competitive analysis platforms.
• Marketing Analytics: Check whether leads were nurtured effectively before being passed to sales and how prospects engaged with marketing materials.

Step #02: Calculate Your Current Win-Loss Ratio

Once you’ve collected your data, the next step is to crunch the numbers and calculate your win-loss ratio. 

Win Rate (%) = Number of Deals WonTotal Number of Deals X 100 

Loss Rate (%) = Number of Deals LostTotal Number of Deals X 100

Let’s say in the last quarter, your sales team worked on 100 deals. Out of those, 40 were won, and 60 were lost. The win and loss rate would be 40% and 60%, respectively.

Don’t stop at the overall numbers. Break your win-loss ratio into smaller segments to uncover patterns:

• By sales rep: Which reps are outperforming or struggling?
• By deal size: Are you winning small deals but losing big ones?
• By industry: Which industries are responding better to your offering?
• By stage of loss: At what stage in the pipeline do most deals drop off?

Step #03: Select Interview Candidates

Talking directly to decision makers—whether you won or lost the deal—provides the why behind the numbers. They’re the ones who understand the reasoning behind the final decision—not just what their team wanted.

The insights you gather from interviews will give context to your data and uncover actionable improvements. 

Here are some tips to shortlist the candidates for interview:

• Focus on deals that closed within the last 30-90 days. Memories fade fast, and recent deals give you the most accurate and detailed feedback.
• Prioritize lost deals first. Their feedback is often brutally honest and valuable, especially if they choose a competitor.
• Use a third party or neutral team member to conduct the interviews if possible. People tend to be more honest when they’re not speaking directly to the salesperson they worked with. A product marketing agency can help with that.
• A small thank-you gift (like a discount or gift card) can encourage participation.
• Keep the interview duration shorter than 30 minutes.
• For deals you’ve won, be careful not to overwhelm top customers with too many interview requests. 

Once you’ve selected the right candidates, you can schedule interviews through Calendly or HubSpot Meetings.

Step #04: Conduct the Interviews

To get meaningful insights, you need to create a comfortable space where interviewees feel they can speak openly. Before the interview, you should learn to avoid asking questions you already know.

• The timeline of the deal.
• The deal size and pricing discussions.
• The prospect’s industry, company size, and business model.
• Specific pain points or challenges the prospect shared during discovery.
• Features or services they expressed the most interest in during the sales process.
• Objections they raised during discussions and how your team addressed them.
• The stage at which the deal was won or lost (e.g., after a demo, pricing negotiation, etc.).
• Competitors they mentioned or were evaluating alongside your solution.

Here’s a step-by-step process to conduct the interviews:

1. Set the Tone: Start with a friendly introduction. Thank them for their time and explain the purpose of the interview. Make it clear this isn’t a sales pitch—it’s about improvement.
2. Record the Interview (With Permission): Recordings ensure you don’t miss any insights. Just let them know you’re recording for internal purposes.
3. Stick to Open-Ended Questions: Let them do most of the talking. Questions like, “What stood out about our competitor’s offer compared to ours?” or “Was there anything we could have done differently during the process?” invite detailed feedback.
4. Dig Deeper When Needed: If their answers are vague, follow up. For example:

• “You mentioned pricing was an issue—was it the upfront cost or the long-term ROI?”
• “You said the demo didn’t meet expectations—can you tell me more about what you hope to see?”

1. Don’t Argue or Sell: This isn’t the time to defend your pricing or pitch a feature they missed. If they bring up a negative, acknowledge it and move on.
2. End on a Positive Note: After gathering feedback, ask them if they have any suggestions for how you can improve moving forward. Thank them again for their time, and emphasize how much their input helps shape your approach.

The specific questions you ask will depend on the goals of your win-loss analysis. However, here’s a solid starting point:

• How would you rate your overall experience with our sales process?
• If you chose a competitor, what tipped the scale in their favor?
• If you didn’t move forward with anyone, what held you back?
• What could we have done differently to win your business?
• How did our pricing compare to other options you reviewed?
• Was our sales process too fast or too slow?
• Was there a specific moment or factor that led to your final decision?

Step #05: Compile and Analyze the Results

Once the interviews are complete, organize all the feedback and data into clear categories, such as pricing, product features, competitor insights, sales process, and customer objections. 

Look for recurring patterns and trends across multiple interviews using Tableau, Power BI, or Google Data Studio. Break down the data by key segments, like deal size, industry, or sales rep, to identify where your strengths lie and where improvements are needed. 

Final Thoughts

The win-loss analysis is not a one-time event. It should be an ongoing process integrated into your sales strategy.

Want to implement a robust win-loss analysis process but don’t know where to start? Aventi can help. Our experienced sales and marketing professionals can guide you through every step. We can help with data collection, analysis, and development of actionable strategies for improvement.

Contact us today for a free consultation.