Below is a list of Win/Loss questions you can consider asking in your Win/Loss interviews, as well as an explanation as to why they’re valuable. You can categorize these questions into various stages of the customer journey—ranging from initial discovery to post-decision reflection.
Why it’s a good question: This question provides insight into how effective your marketing and awareness campaigns are. It helps you understand where leads are coming from—whether through word-of-mouth, online advertising, social media, or industry events. By knowing what channels are driving the most awareness, you can allocate resources more effectively.
Why it’s a good question: The answer here can give you a clear understanding of the customer’s pain points. If you know the problem they were facing, you can ensure that your product’s messaging and positioning clearly address it. Moreover, if they weren’t a good fit for your product, it can help refine lead qualification in the future.
Why it’s a good question: This question digs into the core factors that influence decision-making. It reveals the priorities and features most important to the prospect, such as price, ease of use, scalability, or customer support. Understanding their criteria can help you adapt your sales pitches and product development.
Why it’s a good question: Knowing your competitors is crucial. This question helps uncover who else is in the mix and allows you to identify strengths and weaknesses in comparison to your competition. If you win, you’ll understand what set you apart; if you lose, you can learn why the other product was a better fit.
Why it’s a good question: Instead of just asking what other solutions they considered, asking about their thoughts on those solutions gives you deeper insights into their perception of your competitors. This can highlight areas where competitors may have a leg up or where they are falling short.
Why it’s a good question* The directness of this question is valuable. If you won, it helps you understand which elements of your offering resonated the most, and if you lost, it provides you with specific feedback on what failed to meet the prospect’s expectations. This is one of the most important questions for improving your product or sales process.
Why it’s a good question: A smooth, well-structured sales process can make or break a deal. This question gives you feedback on how your sales team performs. Were they too aggressive? Not responsive enough? Did they provide enough information or seem knowledgeable about the product? You want to understand how your team’s actions affected the final decision.
Why it’s a good question: Every decision-making process comes with hesitations or obstacles. By asking this question, you can uncover roadblocks that might not have been evident during the sales process. These insights can help you preemptively address similar issues with future prospects.
Why it’s a good question: Even in a win, there are often hesitations. Understanding these hesitations helps you refine messaging, address objections earlier in the sales process, or improve product features that are commonly viewed as weaknesses.
Why it’s a good question Customers often enter the evaluation process with preconceived notions about a product or company. Asking what surprised them—whether it was a positive or negative surprise—can highlight gaps in your marketing, unexpected strengths, or areas that need more clarity in communication.
Why it’s a good question: This question can reveal whether your product exceeded or fell short of the prospect’s expectations. If they expected more, it could mean that your sales or marketing efforts overpromised. If you exceeded expectations, that’s valuable feedback to integrate into future pitches.
Why it’s a good question: Decision-making is often difficult, and this question helps you identify ways to simplify the process for future prospects. It might highlight where more resources or clearer information are needed, such as case studies, product demos, or pricing transparency.
Why it’s a good question: Understanding the full landscape of decision-makers is essential, especially in B2B sales. If there were multiple stakeholders, it’s crucial to know who they are and what their concerns were. This helps in tailoring future outreach efforts to all the relevant parties.
Why it’s a good question* This question helps clarify the internal decision-making process within the company. Was the decision based purely on budget? Did someone with veto power sway the decision? Knowing this can help you focus your efforts on the right individuals in future sales cycles.
Why it’s a good question: Budget constraints play a significant role in decision-making. This question helps you gauge whether pricing was a factor in the win or loss. If your price was too high or too low, you can adjust your pricing strategy or find ways to better communicate value.
Why it’s a good question: While price is often a factor, it’s not always the main driver. By understanding the weight of pricing in the decision, you can determine whether your value proposition needs to be stronger, or if your pricing needs adjusting to better meet market expectations.
Why it’s a good question: This gives you insight into how well your messaging has resonated and how customers perceive your value. It also helps you understand the language and framing customers use, which can be useful for refining your own marketing.
Why it’s a good question: This question uncovers potential gaps in your offering. It allows you to gain ideas on what could improve the product and helps you prioritize future development based on real customer feedback.
Why it’s a good question: Excellent customer service can differentiate you from competitors. This question provides feedback on whether your team was helpful, timely, and courteous. It also shows you areas where customer support might have influenced the prospect’s decision.
Why it’s a good question: This is the classic Net Promoter Score (NPS) question and is one of the simplest ways to gauge customer satisfaction. A high likelihood of recommendation indicates a strong product-market fit, while a low score can highlight dissatisfaction or unmet expectations.
Why it’s a good question: If they chose a competitor, this helps you understand what you could have done differently. It could reveal that a different price point, a feature set, or even a different interaction with a salesperson could have swayed the decision in your favor.
Why it’s a good question: Knowing the length of the decision-making process provides insight into your sales cycle. If prospects take too long to decide, it could mean your sales funnel has bottlenecks or that the information provided during the process is insufficient. Alternatively, it may signal that customers are not fully confident, requiring additional nurturing.
Why it’s a good question: Every decision has a tipping point—whether it’s a particular feature, pricing, a relationship with the sales team, or a competitor’s shortcoming. By understanding the final straw that pushed the prospect one way or the other, you can focus on the most impactful elements of your offering.
Why it’s a good question: This question helps you gauge whether your service level aligns with industry expectations. It allows you to ensure that you’re providing the kind of support, pricing transparency, or product innovation that customers expect in your industry.
Why it’s a good question: Sometimes, after further reflection, customers feel differently about their decision. This question helps uncover buyer’s remorse or validate that the choice was correct, giving you valuable data on long-term satisfaction and potential churn.
Why it’s a good question: This helps align expectations
and gives insight into what the customer values most. It also provides valuable feedback on how customers measure the ROI of your product, helping you tailor future marketing and customer success efforts.
Why it’s a good question: Empathy in the sales process is critical. This question helps determine whether your team was able to effectively identify and address the customer’s needs. If they didn’t feel understood, it may indicate a breakdown in communication or discovery, which can be corrected in future interactions.
Why it’s a good question: When you lose a deal, it’s essential to learn what could have changed the outcome. This direct question often provides very clear feedback on what you missed, whether it was a feature, price, or a different approach from your competitors.
Why it’s a good question: Even in a win, it’s valuable to know how close you were to losing the deal. This helps you understand which aspects of the competitor’s offering were attractive, so you can anticipate potential future threats and adjust your strategy accordingly.
Why it’s a good question: Once the deal is closed, new concerns may arise—whether it’s onboarding, implementation, or long-term product fit. Understanding these concerns helps you address them proactively and ensure customer satisfaction throughout the entire customer lifecycle.
A well-executed Win/Loss interview is one of the best ways to gather actionable feedback and refine your business strategy. By asking thoughtful, open-ended questions like the ones above, you can uncover deep insights into your customers’ decision-making process. Remember that the key to effective Win/Loss interviews is not just in asking the right questions, but in listening carefully and acting on the insights gained to continuously improve your offering.
When approached correctly, these interviews are not just about identifying why you won or lost; they are about understanding your market, competitors, and customers on a deeper level.
