11 Questions to Ask in a Win-Loss Review

The hardest part about conducting a win-loss review is often deciding to do it in the first place. If you won the deal, your sales team is probably at a bar tossing back a few rounds. You got the business -- who cares why? Now let’s drink.

On the other hand, salespeople are hardwired to move on quickly after a loss. Maintaining a positive mindset is essential to being a successful seller, and probing into a recent failure is likely a one-way road to Depressionville. 

But 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. Sales organizations that do win-loss reviews outperform those that don’t in most metrics according to Aberdeen -- customer retention rate (60% vs. 48%), percentage of reps attaining quota (51% vs. 47%), and lead conversion rate (23% vs. 17%), just to name a few.

Whether it’s conducted in-house or through a third-party, via a survey or a conversation, here’s a list of questions that could be included 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.)

1) What was the #1 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 amount 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 midmarket 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.” According to CSO Insights, approximately 22% of forecasted opportunities result in 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.

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