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The Win/Loss Analysis Handbook

A win/loss analysis can show you where your efforts are working, and where they aren't.

Done right, it can help you increase revenue and grow your business.

But win/loss isn't just about doing interviews—there are other components too.

Download this handbook to learn everything you need to know about doing a win/loss analysis, including:

  • What not to waste your time on in a win/loss analysis
  • The quantitative and qualitative sides of a win/loss analysis
  • How to choose companies for win/loss interviews
  • Questions to ask if you want to outsource the interviews
  • And more!

Ready to understand your wins and losses on a whole new level? Download the free guide. 👉

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The Win/Loss Analysis Handbook

The Win/Loss Analysis Handbook

Learn how to avoid common pitfalls and get the results you want.


“What’s measured improves.”

That’s what Peter Drucker said more than 30 years ago, and it still holds true today. If you want more business, there’s no better way to find out how to get it than to have a win/loss analysis program… as long as it’s done well.


What Win/Loss Analysis Is—and Isn’t

While win/loss analysis is a type of competitive research, it goes far beyond the old school SWOT analyses you learned in school (though SWOTs can be a valuable part of win/loss reports).

Read story


The Quantitative Side of Win/Loss Analysis

The win/loss calculation: if you want one measurement to tell whether your win/loss analysis has been successful, this would be it.

Read story


The Qualitative Side - Win/Loss Interviews

You’ve heard the old saying “garbage in, garbage out, right? That applies to win/loss interviews too. Who you pick to interview will shape your final report, so really think about who you want to talk to.

Read story


Outsourcing Win/Loss Analysis—Should You?

If your team is really small and really busy, giving them another project (especially one that could be outsourced) may not be ideal. In these cases, you could just hire a win/loss service to do all the interviews for you.

Read story


Win/Loss Analysis Reporting

Once you’ve got all your interviews done, it’s time to sort through and find trends and opportunities.

Read story


The Challenge—and Potential—of Win-Loss Analysis

Good win/loss analysis programs require savvy judgment—both to manage the expectations and sensitivities of people inside your company, and to get information out of customers and prospects.

Read story

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Chapter 01

What Win/Loss Analysis Is—and Isn’t

While win/loss analysis is a type of competitive research, it goes far beyond the old school SWOT analyses you learned in school (though SWOTs can be a valuable part of win/loss reports).

It’s also distinct from other types of research. So "win/loss" isn’t just a new word for an old idea. It isn’t “new wine in old bottles.” It’s a specific type of research with a proven track record.

Win/loss is not:

  • A survey. Surveys are a great tool, and while they use questions like win/loss interviews do, a good win/loss interview is more of a dialogue than a survey could ever be. With surveys, you rarely learn about anything that you didn’t know to ask about. The beauty of win/loss analyses is that they routinely turn up issues you’d never have otherwise known to ask about.
  • Voice of the Customer (VoC). It’s critical to get feedback from customers. But VoC data doesn’t tell you enough about why people chose to not do business with you. It also doesn’t have the depth and flexibility that you get from talking with a customer or past prospect. VoC certainly has its place, but won’t give you the type of holistic, in-depth insights that a win/loss analysis can offer.
  • Done just once. Ideally, your company should have an ongoing win/loss program, not just do a one-off study. Being able to track how your customers’ and prospects’ experience changes over time is critical information. It’s how you know if your efforts to improve are working or not.

The Benefits of Win/Loss Analysis

Win/loss analysis has a long history of getting results. According to the book Win/Loss Analysis: How to Capture and Keep the Business You Want by Ellen Naylor, “taking action from a formal Win/Loss program can improve win rates by 15 to 30 percent.”

Who wouldn’t want to increase their company’s win rate by 15% (or more)?

And if you’re considering the cost of implementing a program like this, you can gauge whether it would be worthwhile very quickly: what would it be worth to your company to close 15% more deals?

Fortunately, closed deals aren’t the only benefit you’ll get. A win/loss program—or even just a one-time analysis—can help you:

  • Better understand your customers’ decision process for buying your products or services.
    • Knowing how your prospects and customers evaluate your offerings will allow you to speak to what they value. It allows you to improve your marketing and sales messaging so you can connect with buyers better—and close more deals.
  • See the gaps in your marketing and sales process.
    • Disconnects in your marketing and sales processes leave prospects without a next step. It’s like having a hole in a bucket that you’re pouring water into—very expensive water. Being able to find and fix those disconnects is key.
  • Know which features of your products or services your prospects and customers value (or not).
    • This information is gold for your research and development department. Why invest an extra million (or ten?) into a feature that no one cares about? Conversely, if you’re considering making upgrades or offering new products or services, wouldn’t it be nice to know if your ideal buyers want what you’re about to invest in… before you’ve spent the money?
  • Learn how your prospects view your products/services compared to the competition.
    • This helps with pricing, positioning, and simply closing more deals. You may also find misperceptions about your company or your products and services that need to be fixed. Or—in some cases—you may find that your competitors are misrepresenting your offerings.
  • Reveal new markets or customer profiles.
    • Marketers know about the concept of a “buyer persona.” It’s a certain type of person or a profile they design marketing campaigns and content for. Personas make for more effective marketing—but only if they’re built on real-world data.

On a larger scale, a win/loss analysis can often reveal brand new markets your company hasn’t even been targeting.

If you can reach those new marketers before your competitors identify them, you’ll have first-mover advantage.

  • Give your C-Suite better insight into how your company is performing overall.
    • Every company takes inventory… of its inventory. But good management includes making an assessment of how your company is functioning as a whole. A win/loss program is an ideal way to do this. It delivers a high-level view of how effective your company is at serving customers and generating sales, while also giving concrete recommendations for exactly where to improve.

Despite all these benefits, most companies’ interest in win/loss is only that: interest. Only 20% of companies actually have a formal win/loss program.

While it might sound like most companies either don’t know about win/loss or haven’t gotten around to it, there may be other reasons. For one, win/loss may not work for every business.

Potential Win/Loss Pitfalls to Avoid

There are real challenges to doing win/loss analyses at all, let alone doing them right. Here are just a few:

1. Sales may be uncomfortable with someone reviewing their work.

Win/loss is actually meant to help sales teams, but it’s common for salespeople to get a little protective about their deals. This is especially true for the “loss” side of win/loss analysis. After all, if you had a big project that failed and someone you didn’t totally trust stepped in to review what went wrong, wouldn’t you feel a little uncomfortable?

Sales teams also most likely don’t want to mark deals as “lost,” rather moving them to “abandoned” or just leaving them open. Either way, these details about these losses won’t be captured in your CRM.

Fortunately, there are several ways to relieve these concerns. First, make it abundantly clear that this is not a Sales evaluation. Good win/loss analysis reviews all aspects of the buyer’s journey, including brand positioning and product performance. Sales’ reputation is no more on the line in this work than any other department.

2. Win/loss needs a champion.

As with many projects, if there isn’t executive backing for a win/loss program, the project is doomed from the beginning. This is in part just due to the competition of priorities, but it’s even more pronounced in win/loss analysis because there are so many departments and players involved. Without strong executive support, coordination may not be as smooth or as free as it needs to be.

Not only that, but the final outcome may also go nowhere without C-Suite’s support. Win/loss is ultimately about implementing what’s discovered, after all. Without the implementation, it’s a nice fact-finding exercise, but ultimately it’s just more data. You have to use the insights you discover.

3. It needs customers and prospects who are willing to talk to you.

Everybody is busy. Really, really busy. If we can barely get people’s attention when we have something they want (a product or service they need to buy), can we really expect them to give us their precious time when they don’t need anything from us?

That’s the first challenge of getting win/loss interviews lined up. Then there are the expectations. If you’re doing a loss interview, will the ex-prospect understand and relax because you’re not actually doing another covert sales pitch? Will an existing customer, who hopes maybe they can get a discount or some soft benefit from talking to you, actually tell you the truth about their experience with your company?

4. Not all company cultures are resilient enough to recognize opportunities for improvement.

Will the different teams, departments, and individuals in your company be receptive to any suggestions a win/loss analysis finds? Be honest, because not every company can actually say yes. If you’re going to spend a lot of time and money getting these insights, only to have people say, “Thanks, but we’ll keep doing what we’ve been doing,” then maybe there are other projects or investments you could make that would actually generate more returns.

5. You need an interviewer who can get people to talk to them candidly.

Don’t skip over this. Good interviewers are hard to come by, and win/loss interviews can be challenging. You want a very special person doing these interviews. Preferably not someone from Sales, as they’ll bring too many biases. Research from the Anova Group, summarized in the book From a Good Sales Call to a Great Sales Call, shows that salespeople actually understand why a sale closed or not only about 40% of the time.

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Chapter 02

The Quantitative Side of Win/Loss Analysis

The win/loss calculation: if you want one measurement to tell whether your win/loss analysis has been successful, this would be it.

Measure your win/loss ratio before you run the analysis, then about six months to a year after the report has been submitted and you’ve begun implementing its results.

Here’s how it’s calculated, along with an example of 16 closed deals against 24 lost deals:

win loss ratio calculation

While you'll probably have a lot of qualitative data to find and process, it's important that a win/loss analysis includes certain quantitative measurements.

Some of these figures can come from internal data, and some may require external inputs. Let’s focus on the internal information first.

Step 1: Assess your win/loss ratio for different types of prospects and markets.

Create a report of all your wins and losses for the last year or two. Then break that data out by:

  • Industry
  • Company size
  • Geographic area
  • Business type (e.g. government, non-profit, B2B, or B2C)
  • The competitor who won the business
  • Product or service
  • Prospects’ situations (like whether or not they have an existing solution in place)

Look at the win/loss ratio for each view and category within those views. If you can, and you have enough data to do it, consider overlaying some of the categories—to show B2B versus B2C companies in Germany, for instance.

You may also want to add deal size and the length of the sales cycle to this information. Just be choosy—having too much data can be as unhelpful as having too little.

It may take some work, but you’ll see some opportunities that wouldn’t have surfaced any other way. There may also be some areas where your company’s win/loss ratio is so weak that it warrants a discussion of abandoning that segment.

This sort of high-level sorting of win/loss data is exactly the type of information that executives value. For example, if your company has a 3:1 win to loss ratio in a particular country but you haven’t invested much there, that win rate alone may justify further investment. Alternatively, if your firm has won only one out of the last nine deals that were pitched to government prospects, maybe it’s time to stop investing Sales’ time in government clients.

Now, let's look at quantitative data from external sources.

Step 2: Get quantitative data from your prospects and customers.

We mentioned earlier how surveys alone aren’t enough for a win/loss analysis. But they can be an important part of one. This is a way to get quantitative data from prospects and customers in a fairly painless way.

Many companies send follow-up emails that ask prospects and customers to answer a few brief questions. Try to limit the questions to 10 or less to get more people to actually finish the survey. Also consider incentivizing survey completion—a popular way to do this now is to say “we’ll buy you a cup of coffee,” and give away a $5 coffee card for each completed survey. These can be sent via email, which makes execution a bit easier.

As with every prospect or customer contact, get feedback from other departments about what you ask. Sales, for instance, may have some key questions they’d like answered. And your executive champion may want to contribute some ideas. So might Marketing, Customer Success, and R&D.

Step 3: Compare benchmark data for your industry to your company’s internal metrics.

Does your industry generate benchmark reports for key business goals and processes? If it does, that information belongs in your win/loss analysis, too.

It’s important to know where you stand on key metrics like retention, deal size, sales cycle length, and more. You may not be able to find a benchmark for every metric your company tracks, but if you can find even some of the data, include it as a section in your final report, including an assessment about why your company is doing better, worse, or about the same as other firms in your industry.

Copper Win Loss 04
Chapter 03

The Qualitative Side - Win/Loss Interviews

You’ve heard the old saying “garbage in, garbage out, right? That applies to win/loss interviews too. Who you pick to interview will shape your final report, so really think about who you want to talk to.

How to Pick Companies for Win/Loss Interviews

To start with, try to interview as many lost accounts as accounts you’ve won. It’s important to understand both groups, and your analysis will be skewed if you don’t.

Also, for the “loss” interviews, don’t pick companies that bailed out of your sales process early. You want to be talking to the companies who came right up to closing a deal, then abandoned the process. You should also interview a few companies that had been clients, but left. Retention matters just as much as acquisition.

Your CRM database will probably have quite a few examples of these late-stage losses, as well as a good-sized list of companies that became customers. For your “win” interviews, pick the types of companies you want more of. So, for example, if you want more government clients, try to get a decent number of won government interviews for your analysis.

You’re going to need at least 10 interviews (five wins, five losses) to be able to see trends and similarities. If you can get as many as 20 interviews, great—you’ll have a better understanding of your business.

To get just 10 interviews, you’ll probably have to reach out to about 50 companies. That allows for the reality of how few people will respond. A 20% hit rate is about average.

If you want to increase your chances, consider offering gift cards, but many win/loss experts say that incentivizing interview subjects can sometimes taint the process. That said, if you’re having trouble getting people to say yes, and you’ve tried to reach them multiple times through multiple channels (like email, phone, and social media, and maybe even direct mail), then you may have to resort to an ethical bribe to get them to talk to you.

Of course, your sales department should be consulted as well about who to interview, as should your executive champion—they might have a few companies they’d like to have included. Also ask for some sample questions from different departments. The more input and contributions you can get up front, the more likely it is that your final report will be useful and actionable.

How to Approach Companies and Set up Interviews for Win/Loss Analysis

This phase of win/loss analysis is all about the ask. How you ask a past prospect or an existing client can have a big effect on whether they’ll agree to give you half an hour of their precious time.

Here are five ways to set yourself up for success:

1. Tell companies that you do random win/loss interviews—while they are still prospects.

It’s all about expectations. So if a salesperson mentions in passing that your company does win/loss analysis and that you might reach out to this prospect again, they’ll be more likely to say yes later on.

If Sales doesn’t want to do this, it’s possible to have an executive mention the interview. Many larger deals are closed after senior teams meet together, so that C-Suite camaraderie can be used to smooth the way for an interview later.

2. Talk to Sales to get a sense of the interview subject and which channel is best to reach them through.

Don’t reach out to interview subjects without getting some input from Sales. The key salesperson on the account often knows when to reach out—and which channel to reach out through. They can also give you valuable information about your interview subjects’ communication preferences (call, or Google hangout, or email interview?), and share information about what they’re like to talk to.

Because your success with this interview will depend on how well you can get your subject to open out and talk, the more you can learn about them beforehand, the better.

3. Interviews will probably take only 20 to 30 minutes.

Stress this in all communications, and get organized enough to stick to this time limit. Everyone is busy—use their time accordingly.

4. Save time with this sample email invite for a win/loss interview.

You don’t necessarily have to reach out to someone via email, but as it’s still the primary business channel, here’s an example of what an interview request might look like.

Dear [Past Prospect],

About four months ago, you and your team at XYZ Corp showed considerable interest in our product/service X. While you ultimately didn’t purchase that solution from us, we greatly valued your interest. Because of that, I’d love to speak with you—briefly, for no more than 30 minutes—to discuss your experience with our company.

Please understand that this isn’t a sales call (or a last-ditch plea to work with us). We’re conducting win/loss interviews with several past prospects and especially wanted to speak with you.

The interview would be done remotely, via phone or Google Hangout, whichever is easiest for you. It would be recorded, though I can waive that if you’re not comfortable with being recorded.

Ideally, I’d like to talk to you sometime during the week of March 5th, or whenever is most convenient for you.

If you have any questions about the interview, just reply to this email, or reach out to me by phone at XXX-XXX-XXXX or via LinkedIn. My profile is at [LinkedIn URL].

Thank you,

That’s certainly not the only way to write an interview request, but use it as a starting point. Try a few different emails to see which one tends to get the best response.

5. Call if you don’t get a reply via email.

You may have to be persistent to land an interview with some people. So try a follow-up email, and if that doesn’t work, try calling them or reaching out via social media.

Here’s an old journalist’s trick that might help: if you call, leave a message the first time you don’t reach them. Then don’t leave follow up voicemails—you’ll only look needy and desperate. Keep calling and not leaving a message. If you do reach them, act like you just happened to call them this second time. Don’t let on that you’ve tried to reach them seven (or 17) times.

How to Do Win/Loss Analysis Interviews

Now things get real. You’ve picked the ideal interview subjects, and they’ve agreed to talk to you. You’ve done your research, so you know a bit about their experience with your company, a bit about their company, and a bit about them as individuals.

Now it’s time to talk. Here are a few tips for pulling off the perfect interview.

1. Pick your interviewer carefully.

It takes a certain sort of person to do good win/loss interviews. They need to be persistent, but not pushy. They should be someone people just naturally tend to talk to—the sort of person people will tell their life story to. A good interviewer will know when to speak up and help an interview subject describe what they mean, and when to keep their mouth shut and let someone be quiet for a moment before they answer.

Ideally, your interviewer should also be as objective as possible, which is why salespeople aren’t usually a good pick for this task. And it can be why outsourcing your win/loss analysis is a good choice (though not always).

2. Use a variety of interviews: email, in-person, video, phone, etc.

Be flexible about which medium you use to interview someone. For instance, in-person may be ideal, but also not feasible if your interview subjects are out of town. Phone interviews can work well, but they don’t let you see someone’s expressions during the interview—so a video interview or Skype call may be a better choice. Finally, while email interviews aren’t considered ideal, they are far better than nothing.

If you can get a subject to respond to you, but they won’t agree to do the interview, introduce some options for different channels. Someone who would shy away from a video interview might be completely fine with a phone call.

3. Research each interview subject before the interview.

Know thy subject: Both the company and the person you’re about to interview. You’ll build trust way faster if you’ve clearly done your homework, you’ll ask far better questions, and you’ll get better answers. It’s just basic due diligence.

4. Prepare questions for the interview.

This is another part of basic due diligence. While some super-experienced win/loss interviewers might be able to just hop on the phone and “wing it” with an interview subject, don’t try that at home. Write down several questions—at least 10.

Now comes the important part: try to guess how the subject might answer each question and write a couple of follow-up questions to their answer. This forces you to think more deeply about your subject, which in turn makes you a better interviewer.

5. Be flexible while you interview. Let your subject talk.

Do you tend to talk more when you’re excited or under pressure? If you do, try really hard to suppress that instinct during your interviews. Often, we get so focused on what we think we know about our interview subject, and so focused about getting our questions answered that we can miss truly golden information—or even interrupt our subject while they’re trying to tell us something critical.

So be careful: be ready to speak, but also ready to stay quiet. And never forget one of the key interviewing skills/tricks: people often say the most valuable things after they’ve paused for a couple of seconds. Don’t just jump into the silence. Wait a moment, even if it feels awkward.

6. To record, or not record?

Of course, if you can get recordings of your interviews, that’s better. You’ll be able to play them for your presentation, for one thing. But you’ll also have a better record of people’s emotions around what they said.

Remember though, some states have laws about recording people—especially if the people haven’t been told they’re being recorded. And some interview subjects will give you a flat “no” to your interview request as soon as you mention a recording device.

So be flexible. And if you’ve been getting a low response to your interview requests (like less than 20%), consider cutting any mention or use of a recording device.

7. Decide if you will compensate your interview subjects.

There’s no real consensus on this. Some win/loss experts say that paying people can color how they answer interview questions. Others point out how busy people are, and that they deserve to be paid for their time and their very valuable input.

Probably the best answer to this question is that if you can get people to agree to interviews without compensation, do it. If you can’t, pay them. “Pay” is usually $50 to $100 per interview, typically paid with something like an Amazon gift card.

8. Say thank you afterwards.

This is another opportunity to give a “gift” or to compensate your interview subjects. At the very least, send them a follow-up email to say thank you.

Copper Win Loss 05
Chapter 04

Outsourcing Win/Loss Analysis—Should You?

If your team is really small and really busy, giving them another project (especially one that could be outsourced) may not be ideal. In these cases, you could just hire a win/loss service to do all the interviews for you.

As with any hire, do your due diligence before you hire a win/loss analysis firm. Check their references and get detailed examples of what they will and won’t do. For instance, will they:

  • help pick which firms to interview, or do they expect you to just give them a list?
  • interview your sales team and even your executive team before the interviews, to get some background information?
  • include recommendations, all notes, and even recordings of their interviews?
  • compensate the people they interview?

You need to know all that beforehand. Don’t expose your clients or past prospects to a company that’ll give them a bad experience.

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Chapter 05

Win/Loss Analysis Reporting

Once you’ve got all your interviews done, it’s time to sort through and find trends and opportunities.

How to Prepare and Present a Win/Loss Analysis Report

This can be easier said than done. If you’ve done 10 half-hour interviews, you’ve probably got about 35,000 words worth of materials (given that the average person speaks at about 150 words per minute, and each interview has about 25 minutes of speech). That’s enough to fill a whole book—and your team doesn’t have time to read a whole book.

So you’re going to have to distill this material. To do that, reread all the transcripts and listen to all the interviews for a second time. Take detailed notes, looking for trends. Notice what words or phrases your interview subjects tend to use. These details might seem like overkill, but being able to speak in the voice of your clients is critical—and something that your friends over in Marketing consider to be copywriting gold.

However you organize the data, do it in a way that fits with your company culture. That might be an Excel document, or a Trello board, or even a wall of Post-it notes. Use whatever format people in your company are most likely to respond to.

The value of your research and your report depends on your teammates actually reading and internalizing the information you share with them.

So use whichever format you think they’re most likely to engage with (in addition to your written report, of course).

One format that many win/loss reports use is a SWOT analysis. (That’s a “Strengths, Weaknesses, Opportunities and Threats” analysis.) Usually it’s broken out into four quadrants, like this:

swot analysis example

You can do a SWOT analysis for your overall win/loss findings, or for each of your primary competitors, or for specific areas (like for a particular product or market you serve). SWOTs are very flexible, and can be great for executive summaries, too: If you know your boss isn’t likely to read anything longer than a page, a half-page SWOT can convey key ideas that might otherwise get skipped over.

How to Make Recommendations in Your Win/Loss Analysis Report

When you get around to recommendations (and you should have a section for them), be careful. You don’t want to label anyone or any team or department as underperformers. Instead, focus on what can be improved, and call out places where teams or departments are doing a particularly good job.

If you feel like you have to be frank about a particular area of weakness, try to mention a few positive things for every negative thing you have to report.

This might seem like a stretch, but research published in The Harvard Business Review has found that the highest-performing teams tend to use a 5.6 to 1 ratio for delivering negative feedback. (As in for every negative thing that’s said, there are about five or six positive things said).

Hopefully, you’ll have found enough good things your company is doing to pull off that ratio. If not, it’s still important to relay the information. Just try to not make anyone feel scorched by your report.

Also consider breaking out recommendations for key teams or departments. For instance, consider having a page or half page summary of recommendations and findings for Product Managers, Sales, Marketing, R&D, and Customer Support.

It might seem like you’re just reiterating what’s been said elsewhere in your report, but let’s face it: everybody wants to know how information applies to them. If you can make that crystal clear, people are more likely to actually read your report—and maybe even act on it.

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Chapter 06

The Challenge—and Potential—of Win-Loss Analysis

Good win/loss analysis programs require savvy judgment—both to manage the expectations and sensitivities of people inside your company, and to get information out of customers and prospects.

You’ll need someone who is trusted and respected, both to do the interviews and to deliver the information they learn from those interviews.

That’s hardly impossible, though. Almost every office has one person who tends to be everyone’s confidant. And if you can give your win/loss person or team the authority and the time to do their work, they may be able to find major opportunities for improvement in your business.

Win/loss is no quick fix, but it’s worth the work if your company can invest in long-term results.