How to Conduct Win-Loss Analysis: A Step-by-Step Guide

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Analytics & Reporting : 8 min read

How to Conduct Win-Loss Analysis: A Step-by-Step Guide

A win-loss analysis is the process of finding out exactly why a prospect bought your product—or why they didn’t.

They’re important because if you don’t know exactly what’s working for your company and what isn’t, you’re essentially winging it. And “winging it” is not part of the sales cycle.

According to a study by Aberdeen Group, companies that conduct win-loss analyses have higher retention rates, lead conversion rates, and annual revenue growth versus companies that don’t.

Despite this, less than 20% of companies actually conduct win-loss analyses. Don’t be part of this statistic.

Here are just some of the things you can learn from a win-loss analysis:

  • How your product or service is perceived in the market
  • Insights on competitors and where their product stands in comparison
  • Which aspects of your unique selling proposition are most important to your prospects
  • Which competitor features are taking sales away from your company

Okay, so how do you do it?

Well, for starters, your CRM should have a designated field for your sales reps to enter a win/loss reason into every time they win or lose a sale. You’ll then easily be able to pull regular reports where you analyze the findings from this field and discuss them with the rest of the team.

win-loss custom fields in copper crm
Really want to get down to the nitty-gritty of your wins and losses? Conduct win-loss interviews to ask prospects directly why they did or didn’t choose you.

This will help you better understand what prospects are looking for so you can make the necessary improvements to your business, whether it’s to your sales process, marketing strategy, or product design. These improvements will result in better customer relationships in the future (and as a result, help you close more sales).

We’ll focus on how to conduct these win-loss analysis interviews in this post, going over each step in detail below.

how to conduct win-loss analysis: Step 1: Find your current win rate + win-loss ratio. Step 2: Outline the specific goals of your win-loss analysis. Step 3: Gather appropriate interview candidates. Step 4: Determine the logistics of the interviews. Step 5: Put together a list of questions to ask. Step 6: Decide who will conduct the interviews + prep them. Step 7: Conduct the interviews. Step 8: Compile, share, then act on the findings.

Step 1: Find your current win rate + win-loss ratio.

Before you can focus on making improvements, you need to know where you currently stand. To do this, you’ll need the following information:

  • # of won opportunities
  • # of lost opportunities
  • # of total opportunities (including opportunities still in progress)
how to calculate win rate
how to calculate win-loss ratio

Step 2: Outline the specific goals of your win-loss analysis.

Ask yourself exactly what you’re trying to gain from your analysis.

Write it down.

For example, your goal could be one or more of the following:

  • Improve sales effectiveness
  • Improve product features or service benefits
  • Strengthen your value proposition to better cater to prospects
  • Improve customer retention rate
  • Better understand buyer behavior
  • Get ideas for future product development
  • Identity service gaps

Keep in mind that win-loss data is valuable to everyone at a company, not just salespeople.

For example, if an interview with a prospect reveals that the reason a sale fell through was because they felt the product wasn’t accurately portrayed in marketing collateral, your Marketing —and Sales—team will definitely want to know that.

Conducting a win-loss analysis interview can be a long (and expensive) process. Because the results will be relevant to the company as a whole, a meeting should be called where reps from all departments can come together and brainstorm goals together. This way, you’ll all get the maximum amount of value out of it and everyone will be equally invested in the results.

Pro-tip: This is also a good opportunity to build internal relationships among departments, especially between Marketing and Sales. To make things easier, download the win/loss analysis checklist.

Step 3: Gather appropriate interview candidates.

You’re going to need to reach out to a good chunk of your prospects and customers to conduct your interviews. Here are some tips when gathering participants:

  • As a general rule of thumb, invite 4x more people than you actually plan to interview. If you’re a small business, you should aim to have at least five people come, so invite 20. If you work at a larger company, invite 80 people and hope 20 of them can make it.
  • Aim for a fair split of won and lost opportunities to capture proportionate data on both sides.
  • Make sure the participant is the decision-maker since they were the one to ultimately call the shot.
  • Consider offering an incentive like a gift card to entice people to participate.

When reaching out to interview candidates, make sure it hasn’t been longer than four weeks since the sale went or fell through. This will ensure the details of their experience are still fresh in their mind. Tell them what you want to discuss ahead of time and explain your only agenda is to improve through their feedback.

Step 4: Determine the logistics of the interviews.

Don’t overlook the logistics. Here are some answers you should nail down before moving on to the next step:

  • How will the prospects be contacted?
  • How long will interviews be? (Limit interview time to 30 minutes, tops.)
  • Where will the interview take place? Over the phone or in-person?
  • How will data be communicated to rest of the company after the interview?
  • How will changes be decided?

Step 5: Put together a list of questions to ask.

Remember those goals you set earlier? Your list of questions will help you uncover the information you need to accomplish them.

Going back to our logistics, your interviews should cap at 30 minutes but ideally be shorter than this. To ensure you stay within this timeline then, limit your interviews to 10-15 questions.

Some examples of questions could be:

  • What was it about our company that initially attracted you?
  • What were the top 1-3 factors you were looking for in a provider?
  • In our sales conversations, how well did you feel we catered to your unique business needs?
  • When shopping for products or services for your business, what’s your decision-making process like?
  • What did you like the most about our offering? What did you like the least?
  • In your eyes, what’s the biggest difference between us and the competition?
  • How would you describe our reputation in the industry?
  • What other companies did you consider during your buying process?
  • Was your experience with our company what you expected before you spoke to us?
  • Why did you ultimately choose to go with/not go with our company?
  • What’s one piece of advice you’d give us for the future?
  • Would you recommend our company to other people?
  • Do you have any other comments or suggestions you’d like to add before we wrap up?

Pro-tip: Be sure to include questions covering the prospect’s whole buying process, from what problem they were trying to solve when they starting shopping for solutions, to what it was that made them consider (or turn away from) your product.

Step 6: Decide who will conduct the interviews + prep them.

Win-loss analysis interviews have to be conducted in a neutral zone—aka. not in a sales environment and with someone they don’t need to worry about offending with their feedback.

For this reason, having salespeople conduct the interviews isn’t the best idea as they’re likely to get defensive.

On the interviewee end, knowing they’re speaking to a sales rep may cause them to censor their feedback as well to avoid offending them, which will impact the accuracy of your data.

To ensure a neutral environment and to avoid any conflicts of interest, hire a third-party interviewer. If you do go this route, make sure the interviewer understands your business and the industry it’s in. This way, if an interview goes off-script at any point, they’ll be able to go with the flow.

If you prefer to use an in-house interviewer, your marketers would also make pretty good candidates since they aren’t directly tied to the products and therefore are less likely to take product or sales process criticism personally.

Once you’ve decided who will conduct the interviews, prep them by going through the script together as well as your goals so they can deliver your questions as effectively as possible.

Step 7: Conduct the interviews.

You (or the person conducting the interview) should have the following in front of you when speaking with an interviewee:

  • Participant’s name
  • Contact information
  • Job title
  • Interview date
  • List of questions + a space for the answers
  • Additional space to add sales notes

It’s important to have a standard interview form to through to ensure uniformity and easy comparison of interviews later.

Start the interview off by introducing yourself and thank the prospect for their time. Reiterate why you’re doing this and give them realistic expectations of how the interview is going to go, including topics that will be covered and how long the interview will take. Ensure confidentiality so the prospect knows they can be totally honest.

Then, start going through the questions list. While the prospect is answering questions, avoid selling, arguing, getting defensive, interrupting, or correcting them (especially if you’re going the in-house route with your interviewer).

Wrap up the interview by thanking them again and give them your contact information in case they want to add or change anything later. If an incentive was promised, give them this incentive now.

Step 8: Compile, share, then act on the findings.

Compile all your answers into a single document and share it with the rest of the company: Sales, Marketing, Customer Success, and Product teams, in particular. You may choose to call another meeting with reps from each department to go over the findings together.

Then, analyze the data and use it to create action items to improve your business.

For example, if a lot of interview participants said that one of their top deciding factors in choosing a product is pricing and your price points aren’t competitive, an action item may be to adjust your pricing or even offer a new product with more concentrated value at a lower price point.

If you’re not doing win-loss analyses yet, it’s time to start.

Everyone wants to win, but both wins and losses can give you tons of valuable data. Use win-loss analyses as a tool to continually improve your business.

Remember, companies who listen to what their customers have to say have happier customers. And companies with happier customers close more sales.