15 Win-Loss Analysis Questions to Reinforce Your Sales Process

photo of a salesman looking for questions

Conducting proper win-loss analyses is hands down the most cost effective way to generate essential insights required to grow your business.

Understanding why one prospect became a customer while another went elsewhere will be key if you expect to make your sales process stronger for future bids.

In this guide, you’ll learn:

Let’s start reinforcing your sales process!

UPDATED: This post was originally published Mar 3, 2019. We’ve added 5 new win loss analysis questions! Start using them today.

What is Win Loss Analysis?

Win Loss Analysis is a research technique that involves examining the reasons why a company has won or lost business opportunities. It typically involves gathering information from the customers who chose to do business with the company and those who chose not to. The purpose of the analysis is to gain insights into the company’s strengths and weaknesses, as well as to identify opportunities for improvement.

In a Win Loss Analysis, a company can ask questions such as:

  • What factors influenced the customer’s decision to choose or not choose our company?
  • What were the customer’s perceptions of our company’s strengths and weaknesses?
  • What did the customer think of our competitors?
  • How could we improve our products or services?

By conducting a Win Loss Analysis, companies can gain a better understanding of their customers’ needs and preferences, and use this information to improve their offerings and increase their competitiveness in the marketplace.

15 Questions to Ask Buyers in a Win-Loss Analysis

Simply put, a win-loss analysis is the process of contacting clients after the conclusion of sales activities.

The main goal here is to find out what your company did right or wrong as well as how you can improve your standing in relation to the competition.

The analysis is best conducted within 3 months of concluding sales activities by way of telephone or in -person interviews. However, using online surveys and questionnaires helps make things easier and more streamlined. But no matter which method you use, you’ll need to have some essential questions handy.

We’ve compiled a list of the most important questions to include in your next win-loss review and how to turn simple answers into actionable insight.

1: What is your decision making process like?

The sales process can get very complex, especially if you’re dealing with enterprise sized companies. That’s because company purchases involve many decision makers and stake holders who will weigh in on the sales process.

It could be entirely possible that management was 100% on board with your product but got vetoed by procurement down the line.

Never lose out on a deal because you neglected to get all the relevant stakeholders and decision makers involved.

By asking this question, you’ll be able to determine and separate your golden wheat supporters from the chaff eating skeptics. Maybe you’ll even find out why you didn’t quite close.

But more importantly, the answer you get will allow you to identify and round up all relevant parties in this or any other similar company next time. You’ll be able to address each of their specific needs and get everyone on board from the onset.

2: What key factor influenced your final decision?

This question will surface most of the high level reasons why you’re either winning or losing. However, you need to keep in mind that customers are not as intimately familiar with your product or service as you are.

As such, they could be mistaken or misinformed about the pros and cons. Take the opportunity to educate them and clear up any confusion they may have had.

Getting the client to open up will show you what’s truly important to the customers vs. what you may have perceived as the selling factor.

If you’re selling CRM solutions for instance, you’ll find the needs vary depending on who you ask. Sales rep want a CRM that’s mobile while marketing will want one that integrates with their automation tools. Salesforce may have all these, but it’s up to you to know which features to up-sell to which clients.

Takeaway is, you just can’t pitch the same canned pitch to every client you meet – you’ve got to customize it to suit their needs.

3: What was your experience with our team?

In the famous words of Jill Konrath, “How we sell is far more important than what we sell.”

A single product may not always sell down the line, but a good salesperson will always be selling all the way to the grave. What we mean to say here is that the human element remains a huge part of the buying process. So naturally, it would make sense that the people involved have something to contribute towards the customer’s final decision.

Keeping this question open will allow the customer to avoid restricting their answers to just the sales team. Perhaps they interacted with customer support, marketing or even executives. If any customer was left with a bad taste in their wallet after dealing with anyone in your company, look into this and make sure it doesn’t happen again.

4: How would you rate our product/service?

Salespeople are explicitly tasked with landing new business and closing deals. So whenever a deal goes south, the sales reps are usually the ones taking the full blame.

But just how fair is it to always get the short end of the stick when it’s hardly your fault?

If most of your sales reps are landing prospects, getting meetings, nailing their presentations and still going home empty handed, there could be more to the story. And if there’s more to this story, this question will provide insight into what went wrong.

Dive right into the product or service and ask what the customers liked or disliked about it. The answers will expose any issues that need to be tweaked by the development team.

5: How would you describe our sales process timing?

While not many people appreciate the aggressive sales approach, they also don’t want to be left hanging. A sales process that’s either too fast and furious or too slow and laid back will deter sales. Like goldilocks, you’ve got to get that bowl of sales porridge just right.

If your company doesn’t understand the number of steps in the customer’s decision making process, your team is bound to give the wrong information at the wrong time. If you do find out that timing was an issue, follow up with another question to establish this timeframe and adjust to trends accordingly.

6: Why did/didn't you decide to buy now?

In sales, your team is not just competing against rival companies; you’ve also got the dreaded ‘no decision’ to contend with. Having a clear idea of why a prospect bought or didn’t buy will bring to light any factors that you may not have been aware of.

Once you’ve learnt these factors, you can incorporate any new triggers into your research process and develop plans to address any issues that could put off a buy decision.

7: What's our reputation in the industry?

Before your prospect makes the decision to buy or not, they will have most likely taken a deep dive into the industry. Their research could have taken them to unknown sources and niche forums with all sorts of opinions. Take advantage of that fact and include this question in your win-loss analysis.

Hopefully, you’ll get an honest prospect with no holds barred to give it to you like it really is. Knowing how you are viewed in the marketplace will not only allow you to build on your strengths, but also work on your (perceived) weaknesses as well.

8: What was the biggest difference between us and other considered solutions?

This is a clever and tactful way of asking why you either chose us or went for the competition instead. For better or worse, this question opens the door for prospects to share the differences between you and other solutions in your space.

If you’re missing some crucial features and losing business because of it, your product development team needs to know. If people love certain aspects such as the price, take it as a hint not to experiment with new price ranges this quarter.

9: What's the one thing you'd advise us to change?

Win or lose, this is one question that you need to ask whenever you get the chance. Any company that wants to grow should always be seeking feedback from their prospects.

Good or bad, learn to take the advice to heart and execute change where possible. Customers seeing their concerns addressed will really do wonders for future interactions. And while you’re at it, checkout a few buyer friction points that could be costing you sales.

10: Any additional comments or suggestions?

This question is always a winner because it opens up the conversation and throws the ball in the prospects court. It allows your customers to provide any honest feedback or comments that may not have been uncovered by any other question.

Whether you get negative or positive feedback, make sure you evaluate it and see if there any way your company can improve the process or services to meet your prospects’ expectations.

11. What were the main reasons for choosing our product/service over competitors?

When customers choose a particular product or service, they often consider various factors, such as price, quality, features, and customer service. By asking this question, companies can gain insight into their strengths and competitive advantages compared to other solutions in the market. They can also identify areas for improvement or differentiation from competitors.

For example, a customer may choose a product over a competitor’s offering because of its user-friendly interface or faster response time from customer support. These insights can help companies to enhance their marketing messaging and product development efforts.

12. How did you hear about our product/service?

The source of information or referral can play a crucial role in a customer’s decision to choose a product or service. By understanding how customers learn about a company’s offering, companies can improve their marketing and outreach strategies to reach potential customers more effectively.

For instance, a customer may have heard about a product/service from a friend or colleague, or from an online review or advertisement. These insights can help companies to allocate their marketing resources more effectively and identify areas where they need to improve their visibility or reputation.

13. What features or aspects of our product/service did you find most valuable?

Understanding the specific features or aspects of a product or service that customers find valuable can help companies to focus their efforts on improving or emphasizing those features. This can also help them to better understand their target audience and their needs.

For example, a customer may find a particular feature or functionality of a product to be especially useful in their specific use case. By identifying these valuable features, companies can improve their product development efforts and marketing messaging to better align with customer needs.

14. What areas of our product/service could be improved?

While it’s important to understand what customers value about a product or service, it’s equally important to understand areas for improvement. By identifying weaknesses or areas where customers feel dissatisfied, companies can take steps to address those issues and improve customer satisfaction.

For example, a customer may find a particular feature to be confusing or difficult to use, or may have had a negative experience with customer support. These insights can help companies to prioritize areas for improvement and take action to address customer pain points.

15. What would have made you more likely to choose our product/service?

Understanding what factors could have swayed a customer towards choosing your product or service can help you identify areas for improvement and increase your chances of winning similar opportunities in the future.

By asking this question, you can gain insights into the customer’s specific needs and preferences, and identify potential areas where your product or service fell short. This could include issues such as pricing, features, or customer support. Armed with this information, you can make targeted improvements to your offering that address the customer’s concerns and make your product or service more appealing.

5 Rules of Successful Post Decision Interviews

To prevent inefficiencies and redundancies during a post decision analysis, there are a few ground rules that need to be in place. Here are 5 rules for a successful win/loss analysis to go with your questions.

a) Conduct Win Loss Analysis Within 3 Months of Decision

Research shows that sales cycle knowledge is more credible immediately after a buy or no buy decision is made. What’s more, memory perception tends to diminish a few months after making the final decision. So the more complicated a sales cycle solution is, the quicker the post decision interview needs to take place.

Try to conduct the win/loss analysis interview within 3 months to get the best results. Similarly, start your customer off with a few simple questions to get their mind frame the same as it was when they were making their purchase decision.  

b) Conduct Interview in a Non-Sales Environment

Did you know that the aim of some post decision analysts is to discover any last-minute opportunities to secure the interviewees business? Unfortunately, this is not the time to try and make sales that you feel were lost.

A win/loss analysis environment must be completely free of conflict and judgment if impartial knowledge is to be captured. At the same time, it must be absolutely devoid of salesmanship. That’s why it’s common to find an impartial third party to help with credible interviews as the next point explains.

c) Outsource to an Unbiased Third Party if Unable to Create Non-Sales Environment

Typically, the odds are stacked against companies trying to conduct internal win/loss analysis interviews. The common tendencies that contribute to this problem include a lack of continuity metrics, difficulty achieving objectivity and discretionary priorities.

If the post-decision tasks are too daunting for an organization, it is recommended that the interviews be outsourced. So, how do you identify the best fit for an outsourcing company? The key is to avoid conflicts of interest, ensure deliverable action and select interviewers that understand both your business and its sales cycle.

d) Understand that Perception is Reality

In the world of sales, perception is actually more powerful than reality. Buyers will purchase what they believe is true and best. And if the post decision analysis ins conducted before the buyer can use the product, then the only knowledge the will give is perception.

However, this perception as obtained from the interviews is critical to making a competitive differentiation and aligning a vendor product, company and service to market perception.

e) Use a Structured and Metric Based Template

In most cases, the things a prospect declares after a buy or no buy decision are steeped in emotion. As such, this makes it easier to gauge how they feel than it is to secure tangible, free-form articulation of complex sales cycles.

Although quantifiable evidence is preferred, it’s also essential to capture free-form comments to gain insight into each response. Try to narrow the interview attributes into a single word and group attributes into processes, statistics, criteria and performance categories. It’s really no different than creating email templates.   

Wrapping Up the Win-Loss Analysis

Once your post-sales win-loss analysis is done, make sure to thank the prospect and give them a way to contact you if there’s anything more they may want to add. With the answers to the questions above, companies can get a vivid image of how things stand.

A proper win loss analysis will allow you to move forward equipped with all the information you need to craft an intelligent approach for future prospects.

Did you find this content helpful?

Thanks for your feedback! We would really appreciate your feedback.


Samir Majumdar

Samir Majumdar

Samir is the CEO and Co-founder of Veloxy. After spending 20+ years creating corporate systems, boosting revenue, and eliminating inefficiencies, Samir started Veloxy to help sales professionals shorten sales cycles, accelerate pipelines, and close more deals.