Win/Loss Analysis - How to Do It Yourself?

Data and customer feedback are essential for continuously developing your sales approach, product, and team performance. Without direct input from the market, it becomes difficult to identify and prioritise what to improve. A critical piece of this puzzle is understanding why specific opportunities are won or lost. However, the data companies rely on is often skewed by internal bias.

Sales reps, for instance, may offer their personal interpretation of why winning an opportunity succeeded or failed, but their motivations can influence what they document in the CRM. It’s not unheard of for a sales rep to attribute a lost deal to product limitations rather than reflecting on the sales process or their actions (or lack thereof). Similarly, when deals are won, they can be tempted to overemphasise their role rather than acknowledging external factors like the prospect of simply choosing the most affordable solution.

Moreover, when sales teams seek feedback from prospects, they don’t always receive the entire truth. Buyers may soften their critiques, avoid difficult conversations, or over/underplay their role in the decision. As a result, sales organisations are left with an incomplete picture of what drives their closed won or lost opportunities.

Ask, and You Shall Learn

Without direct input from your customers, you’re essentially developing your sales process, product, and operations blindfolded. Decisions become questimates at best—some development initiatives will succeed, but many will miss the bullseye. Relying solely on internal or CRM data means you’ll inevitably overlook critical insights. By not engaging with your prospects and customers directly, you risk missing the feedback that could guide your next strategic decision in the right direction.

Real-world examples show the importance of looking beyond data and enriching it with feedback from both lost and won opportunities:

• In one instance, we discovered a significant deal was lost because our product lacked essential CRM integration—a gap would have remained unnoticed without customer feedback as it was not documented in the CRM.
• Another deal was won, not because we had the best solution but because our sales team’s persistent engagement showed the prospect we genuinely wanted their business. The sales team thought we won this one with features.
• A so-called "lost" opportunity wasn’t truly lost. We hadn’t followed up enough, and the prospect remained open to further engagement. That call was a surprising one for all involved.

What is Win/Loss Analysis?

This brings us to Win/Loss Analysis, a powerful tool for evaluating why opportunities are closed as won or lost. By reviewing the outcomes of past sales opportunities, you gain a deeper understanding of the key factors behind your team's successes and misses.

The win/loss analysis data is collected from CRM and other internal data sources, as well as by interviewing buyers at companies you have recently acquired as a customer or tried and failed to sell to. Due to the reasons explained above, data from sales activities and feedback directly from (potential) customers are required to form a complete picture. Once the data is collected and analysed, it will expose how to develop the sales process and product further. Actions that could follow such analysis are additional product or sales training, adjusting the sales process or even creating new product features.

Once the data is collected and analysed, it will expose how to develop the sales process and product further.

Conducting win/loss analysis at scale can be resource-intensive. It often requires an external firm to collect the data and perform the interviews, which comes with a significant price tag. The good news is that a DIY win/loss analysis can be equally good, especially for start-ups or sales teams working with limited budgets. This exercise can offer eye-opening insights for those leading sales teams and help early-stage founders refine their approach to achieving product-market fit.

You Can Do a Win/Loss Analysis Yourself

Here’s how to start: As a sales leader or founder, reach out directly to the key contacts involved in a recently won or lost opportunity. Taking a personal approach opens the door to genuine conversations that might not happen otherwise and allows you, as a leader, to collect unfiltered feedback.

Once you initiate making win/loss calls (we strongly recommend phone over email for this), you’ll be surprised at how many buyers will give you five minutes of their time. When the conversation is framed correctly, many appreciate the opportunity to offer feedback on their experience. Even though you’re not a neutral third party like a research firm, decision-makers are often more comfortable sharing insights with you—things they wouldn’t discuss with the sales rep who lost the deal or aspects that might be uncomfortable to bring up right after the sales dialogue.

Conducting DIY Win/Loss Analysis Is Educational

Make notes as you go through your conversations. These notes are worth gold, and you will most likely learn things you would like to return later during 1to1s and even management meetings. We bet that you'll unearth valuable insights through just five initial conversations. Insights that will surprise you, both good and bad.

Through just five initial conversations, you’ll unearth valuable insights.

Moreover, DIY win/loss analysis provides crucial guidance for planning the next financial year and beyond.

Make win/loss analysis part of your regular toolset. When combined with your internal data, you will gather inputs that benefit your messaging, provide valuable input for your product team, strengthen the feedback during your 1to1s, and add context to regular pipeline reviews.