Lihong Hicken is the cofounder and Chief Feedback Officer of TheySaid, an AI-driven survey and interview company.
Ask any sales leader why their company loses deals, and they’ll confidently tell you: “We talk to our customers every day. We know why we win and why we lose.”
Most companies, though, think they are doing win-loss analysis when they aren’t. Instead, they rely on internal opinions, anecdotes or flawed CRM data. True win-loss analysis isn’t about guesses. It means asking buyers why they didn’t buy—without bias or assumptions.
What Win-Loss Analysis Is Not
Most companies unknowingly substitute real buyer-driven win-loss analysis with one of these approaches:
1. Sales-Reported Close-Loss Reasons: Many teams rely on CRM fields where sales reps pick a reason for the loss (e.g., “Pricing,” “Chose Competitor”). This data is unreliable—salespeople often don’t know the real reason or pick a convenient one.
2. Informal Sales Conversations: Sales reps naturally get some feedback in the sales process, but it’s incomplete and inconsistent. Buyers rarely share the full truth—especially if the issue was poor sales execution.
3. Traditional Surveys. Standard post-loss surveys only capture surface-level quantitative data (e.g., 65% said price was a factor). They miss the deeper “why” behind buyer decisions.
The bottom line? If your win-loss process doesn’t involve direct, structured feedback from buyers, it’s not real win-loss analysis.
Why Most Companies Don’t Do Win-Loss Analysis Properly
Even after realizing the flaws in their approach, many companies still struggle with proper win-loss analyses. Why?
1. Manual Interviews By Product Marketing Teams: In-house interviews provide insights, but they’re slow and unscalable—only a few calls happen per quarter.
2. Hiring A Win-Loss Agency: Agencies often charge up to $20,000 for 20 interviews, with insights often arriving too late to act. Despite the cost, the insights are invaluable, so companies should still invest in agencies if they can afford it.
3. Closed-Loss Surveys: Automated surveys provide broad data but fail to capture nuanced buyer motivations, making them less actionable.
As a result, most companies skip win-loss analysis, or only do it once a year—when the insights are outdated.
The Proper Way To Do Win-Loss Analysis
A well-structured win-loss analysis program typically follows these best practices:
• Directly interviewing buyers instead of relying on sales opinions
• Structured questioning to uncover true decision drivers
• Mix of qualitative (interviews) and quantitative (surveys) insights
• Regular cadence—not just once a year
• Actionable insights shared with sales, product and marketing teams
When done right, win-loss analysis helps businesses identify why they lose deals, such as product gaps, pricing issues, messaging misalignment or sales execution flaws. It can also help to fine-tune marketing messaging and sales enablement efforts and improve competitive positioning.
How AI Is Changing Win-Loss Analysis
AI can assist in the win-loss analysis process, as it removes the manual burden and makes win-loss continuous and affordable. Instead of waiting months for insights, AI-powered win-loss enables real-time buyer feedback. Here’s how AI can streamline win-loss analysis:
1. Replacing Manual Interviews: AI-powered conversational surveys capture qualitative insights, mimicking the depth of interviews.
2. Automated CRM Integration For Instant Feedback: The AI survey/interview is automatically triggered as soon as a deal is marked “closed-lost” in the CRM.
3. Higher Buyer Participation Rates: Traditional win-loss interviews require 30-minute calls and a $100 to $150 incentive, yet buyers often don’t participate due to scheduling friction. AI removes scheduling entirely.
4. Fresh, Unbiased Data: Instead of interviewing buyers months later, AI captures insights immediately after a loss—while the deal is still fresh in their mind.
Many companies struggle with AI not because the tools are lacking but because they haven’t trained their teams. Employees often stick to legacy processes, unsure how to adapt—or afraid AI might replace them. Without reframing AI as a tool for efficiency, companies miss the chance to transform how work gets done.
Win-Loss Best Practices
Let’s break down some other win-loss best practices:
1. Getting The Right Answers
AI can generate interview questions, or you can use a template. If you would like to use a template, here are a few good questions to ask:
• What are the main reasons you decided not to go with the product?
• How important was the business need you wanted us to solve?
• Did you participate in a trial as part of your evaluation?
• React to this: The price is reasonable for the feature that it offers.
• How effective was the sales team in quantifying the value the service provides?
• What alternative did you choose, and why?
2. Automated CRM Integration And Survey Distribution
How fresh the deal was last lost is a major factor in getting responses. To get real-time feedback, it’s helpful to automate the process and get the survey to participants as quickly as possible. Here are two strategies for scheduling surveys:
1. Ongoing: Send an email with an AI interview link after a certain event (such as a deal being marked “closed-lost” in the CRM). Pro tip: Send it from an executive’s or consultant’s email to boost responses.
2. Monthly Batch: This is especially valuable for teams with low-volume sales. Still, it’s important to send it no more than a month later, while the buyer’s memory is fresh.
In either case, I suggest sending a reminder email three business days later and a final email three days after that.
3. Incentives
People often ask me whether incentives are necessary to get feedback. My company has tested this question, and I highly recommend paying incentives for participation.
How much is the right amount for incentives? This depends on your buyer’s income level and what you are asking from participants. For well-off participants, when using traditional win-loss, buyers might expect $100 to $200 for a 30-minute interview. With AI win-loss—given that participants can skip scheduling the call—you may be able to get away with offering $25 to $50.
Final Thoughts
If you’re still relying on sales-reported close-loss reasons or once-a-year win-loss studies, you’re leaving critical revenue-driving insights on the table. The question isn’t “Should we do win-loss?” It’s “How much longer can we afford not to?”
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