15 Questions to Ask in a Win-Loss Analysis to Help You Sell Better

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Emma Brudner
Emma Brudner



Win-loss review analysis is one of the most difficult parts of the sales process. If you lost the deal, it feels like you're taking it upon yourself to rub your nose in your own defeat. If you won the deal, it's likely you and your sales team are celebrating. You got the business -- who cares why? Now let’s drink.

win loss review questions

Maintaining a positive mindset is essential to being a successful seller, but probing into a recent failure is likely a one-way road to Depressionville.

Win-loss reviews are incredibly important to perform -- in both cases.

Understanding the reasons why a prospect became a customer, opted for the competition, or made no decision at all makes your sales process all the stronger for future bids.

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What is a win-loss review?

A win-loss review is an interview that helps determine why a sales opportunity was won or lost. These interviews are often conducted over the phone, and can be performed by your company or a third-party service. 

When developing your review strategy, you should be able to answer the following questions:

  • Who will be conducting the interview?
  • What are the criteria for selecting customers or prospects to interview?
  • Which questions will be asked?
  • How long will the interview take?
  • When will the interview be scheduled?

Setting up a strategy for win-loss reviews will help you and your team more successful and close more opportunities. In a 2017 study by CSO Insights, researchers found teams that regularly used win-loss analysis outperformed those that did not. These teams saw a 17.6% increase in seller achieved quota rates. And win rates increased by 14.2% for those who consistently used win-loss reviews.

Whether it’s conducted in-house or through a third-party, via a survey or a conversation, here’s a list of questions that to include in your win-loss review. (Just make sure not to ask all of them -- in-person interviews should be no longer than 15-20 minutes.)

Win-Loss Analysis Questions

1. What was the biggest consideration you based your decision on?

How it Helps: This will surface the high-level reasons you’re winning or losing. Keep in mind that while you’re intimately familiar with your product or service and its pros/cons, prospects don’t have the same experience under their belts. If you’re surprised by a point that comes up in response to this question -- for instance, a feature perceived to be inferior that you know is better than the competitions’ -- use that insight as a jumping-off point for implementing targeted change.

Next Steps: Beware of accepting vague reasons like “price” or “the competition seemed to ‘get’ us better.” Price issues are usually tied to a problem with communicating value, and the common “they just get us” objection points to a problem with your sales process. Keep pressing (gently!) until you uncover the deeper dirt.

2. How well did we do in tailoring our presentation/product/service to your needs?

How it Helps: Personalization is the name of the sales game today. Rather than presenting a canned pitch to each and every prospect, sales organizations should be carefully customizing every detail for the potential client’s needs. A lackluster response here is a gigantic red flag.

Next Steps: If you’re losing deals due to a lack of personalization, you might have problems with undefined buyer personas or a poor understanding of the buyer’s journey. Can your salespeople quickly identify what kind of prospect they're dealing with, and at what buying stage those prospects are in to adjust presentations appropriately? If not, you have some work to do. Alternatively, your reps might need coaching to listen more, talk less, and ask better questions.

3. Did you define your decision criteria? If so, what were they?

How it Helps: Sellers aren’t always privy to buyers’ decision checklists. Knowing how clients are evaluating your product or service can help you decide what features or aspects to play up or down the next time around.

Next Steps: Watch out for criteria out of left field. If potential clients are looking to your product or service for something that it flat out doesn’t do, marketing messaging needs to be adjusted. Conversely, this could be an opportunity to develop an area that your prospects are clearly looking for your company to deliver in.

4. Did you talk to any references about our product/service? What did they have to say?

How it Helps: If you’re like the rest of us, the first thing you do when choosing a restaurant is read Yelp reviews. Same goes for business purchases -- everybody loves to get dirt from a good reference. Getting a sense of what references are saying can help you get a handle on your company’s brand perception.

Next Steps: If you’re hearing negative feedback from references secondhand, you should relay specific complaints to your management team so they can devote more resources to ongoing customer satisfaction. Stem the tide of detractors ASAP.

5. What was your experience with our team?

How it Helps: As Jill Konrath writes in her book Agile Selling, “how we sell is more important than what we sell.” The human element is still a huge part of the buying process, even in our digital age.

Next Steps: Be sure to keep this question open -- don’t restrict it to solely address the sales team. While prospects primarily interact with salespeople, they could also cross paths with marketing, customer support, or executives -- either in person or virtually. If the prospect was left with a bad taste in their mouth after an interaction with any person from your company, probe into what behavior in particular was to blame, and circle back.

6. How did you feel about the timing of our sales process? When did you start investigating a new product/service?

How it Helps: Nobody likes to be left hanging, but they also don’t want to feel rushed along. A process that’s too slow or too fast will deter sales. Think back to your kindergarten days and take a cue from Goldilocks’ insistence on “just right.”

Next Steps: Here’s another area that has implications for the buyer’s journey. If your company doesn’t understand the length or the number of steps in buyers’ research and decision processes, your sales team is bound to present the wrong information at the wrong time. If you sense that your timing was an issue, follow up with the second question to uncover the timeframe of the prospect’s project. If a time trend emerges among several prospects, adjust your pacing accordingly.

7. How do you feel about our road map? Is there anything we’re missing?

How it Helps: It’s possible that you didn’t win or lose based on anything your team presented today. Adopting a new product or service is a significant change management undertaking for organizations, and one they’re not eager to repeat a few months down the line when they realize their choice wasn’t such a great fit.

Next Steps: If road map concerns were a primary reason a prospect signed on with a competitor, direct their concerns back to your management team to possibly adjust your development agenda. If the road map was a primary reason a prospect chose your company, relay this feedback to parties involved in future offers to ensure you can deliver.

8. What is your decision-making process like?

How it Helps: Especially at mid-market and enterprise-sized companies, buying is a complex process that involves multiple parties. It’s entirely possible that one person, say the CMO, could be 100% on board with your product, but procurement vetoed the deal. Don’t lose as a result of neglecting to get all the key stakeholders together.

Next Steps: Identify and round up all relevant parties the next time your team presents to a similar company in terms of size or industry. Address each person’s specific needs -- what a CMO wants is different than what procurement is looking for.

9. How would you rate our product/service? What in particular did you like or dislike?

How it Helps: Since salespeople are the employees explicitly tasked with closing new business, they often get blamed when a deal goes awry. But it's rough to shoulder the blame if it’s not really your fault. Diving into the product or service features can expose issues out of the sales team’s control.

Next Steps: Relay any feature feedback to your development team.

10. Why did/didn’t you decide to buy now?

How it Helps: In B2B sales, you’re not just competing against rival companies; you’re also combatting the dreaded “no decision.” Understanding why a prospect did or didn’t buy can bring to light trigger events or deal-derailing problems that your team may not have been aware of.

Next Steps: Incorporate any new trigger events into your sales research process. Develop plans to proactively address and diffuse issues that could put off a decision.

11. What’s the one thing you would advise us to change for next time?

How it Helps: Win or lose, you should always be seeking feedback from prospects.

Next Steps: Take comments to heart, and execute.

12. What was the biggest difference between us and the other solutions you considered?

How it Helps: This is a more tactful way of asking, "Why did/didn't you choose us over our competitor?" It opens the door for your prospect to share what differentiated you from other solutions in your space -- for better or for worse.

Next Steps: If you're missing a feature your competitor has and losing business regularly because of it, take that data to your product team. If people love your pricing structure, use that as a reason not to experiment with a new pricing plan this quarter. Listen to your clients/prospects and implement what they have to say when you identify trends.

13. How easy did we make this decision for you?

How it Helps: While not always possible, you want to make it easy for your prospect to choose your solution.

Next Steps: If you receive feedback your service was missing a crucial offering making it easy for your customer to choose another company, take that intelligence and improve your service.

14. What is our reputation like within the industry?

How it Helps: Your customer or prospect has just finished taking a deep dive into the industry. Make the most of that and ask them what they found.

Next Steps: Hopefully, you have a pretty accurate and evolving idea of how you're perceived within your marketplace, but it's always helpful to learn more about your reputation -- and how you can improve it.

15. Do you have any additional suggestions or comments?

How it Helps: This opens up the conversation to let the customer or prospect provide any honest feedback that might not have been uncovered from your previous questions.

Next Steps: Whether the feedback is positive or negative, evaluate it and see if there are any ways to improve your processes or service options to meet the customer or prospect expectations.

Win-Loss Analysis Template

It's helpful to have a defined process for conducting win-loss review analysis. Here's a template for how to structure your reviews for success:

1. Conduct a pre-meeting strategy session - Determine what your goal will be for this win-loss review, which questions you should ask, who will conduct the meeting, who will coordinate the logistics, and who will disseminate findings to the rest of the team.

2. Facilitate the win-loss review - Keep your meeting short -- no more than 30 minutes -- to respect your prospect/customer's time. Ask your agreed-upon questions and listen intently. Avoid the tendency to get defensive or jump in with additional comments. And end by thanking them for their time. 

3. Share key meeting takeaways - Write up the most salient points from your win-loss review and share key takeaways with internal stakeholders at your company. If a feature was lacking, reach out to your product team. If your customer service package is what set you apart, congratulate your CS team.

Whatever you do, don't sit on this great information -- share it, iterate on the feedback, and build a stronger company and a better sales team. Looking for more? Learn how to hold an effective postmortem next.

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Topics: Win-Loss Review
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