Competitive Enablement

Competitive Win-Loss Analysis 101: Your Guide to Win-Loss Best Practices

Monday morning win-loss analysis is a matter of course for NFL players. Teams will break off into units by position, and analyze their big wins and losses from the day before. 

Business win-loss analysis best practices share a lot in common with those of the NFL. And while more than a century of professional football has solidified the value of conducting win-loss analysis, most businesses still have a long way to go. 

It goes without saying that the absence of an established win-loss program is a deficit in any competitive intelligence program in any organization. 

Luckily, this guide will give you all the tools you need to start conducting an effective win-loss analysis, understand the objectives of your win-loss analysis interviews, and use the findings to increase sales and win more deals. 

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What is B2B win-loss analysis and why should I care?

Show us a successful B2B company that doesn’t conduct win-loss analysis and we’ll show you a Canadian that doesn’t love hockey. 

(We’re sure they exist somewhere, but they aren’t proud of it.)

That’s because B2B win-loss analysis is one of the most powerful tools at your disposal to gain actionable insights to evolve and grow your company. And if you’re not growing, you’re dying. 

Best practices for win-loss analysis programs

Effective win-loss analysis delivers some of the best primary intel on the perception of your organization from prospects and customers. 
When done correctly, this intel can be turned into insights benefiting teams across your organization, especially, but not limited to, sales. As Jenna Dorman put it in a recent interview:

“By far the most useful tool is win-loss reviews. Understanding what is happening in real-time in the field. What are people saying? Why do we lose? What are our customers saying? Salespeople would say that’s probably the most valuable information they could be getting.” – Jenna Dorman, SVP Global Enterprise Sales at Alida.

Moreover, according to research by Accent Technologies, companies with win-loss analysis programs see higher customer retention rates, and ARR. They’re also more likely to reach their sales quotas compared to companies that don’t. 

The insights gleaned from this intel can and should serve as the basis for strategic and tactical decisions for everything you do, from training and onboarding to product development and customer service. 

Win-loss analysis program value quoted by Jenna Dorman of Alida

Win-loss analysis definition 

Win-loss analysis is the process of analyzing the reasons why a deal was won or lost through questionnaire and other data obtained via CRM tools, as well as interview with prospects, customers, buyers, and your sales reps. 

The benefits 

Insight from win-loss analysis serves every team in your organization tasked with collecting intel about your competitors and your own positioning in the market. But to get right insight, you need a clear objective from the outset, such as:

  • The market’s perception of your product or brand 
  • Competitor features that are beating you out
  • How your competitor’s product compares to your offering
  • What prospects care most about regarding your unique selling proposition (USP)

Of course if win-loss analysis were as simple as interviewing some stakeholders and asking a few questions, everyone would be doing it and you wouldn’t need a guide like this one. 

In reality, a recent survey showed that only 42% of companies conduct regular win-loss analysis. 

Starting your win-loss analysis program 

There are many different directions you can go with win-loss analysis. No matter what, there are always seven components of successful win-loss analysis programs that everyone should know. 

7 components successful win-loss analysis

Getting clear on the goals of your win-loss analysis

Apart from the ultimate goal of winning more business and increasing revenue, it’s essential for you to establish what outcomes you want to achieve through win-loss analysis. 

We recommend that you focus on 1-2 goals at most. Examples of win-loss analysis goals could be:

  • Better customer retention rate
  • Solidify and enhance your sales strategy
  • Deepen understanding of buyer behaviour
  • Farm ideas for product development
  • Improve sales strategy 

Establishing clear hypotheses 

A good scientist always has at least one working hypothesis before heading into an experiment. You’ll need to do the same. 

In the context of win-loss analysis, you should source your hypotheses from internal stakeholders. 

Send out a short win-loss questionnaire with two-three basic questions: 

  • Why do we win against our competition?
  • Why do we lose against our competition? 
  • What’s the biggest reason customers churn?

Gather the results and use them as a guide to form your hypothesis. 

Narrowing the scope of the win-loss analysis

Don’t try to boil the ocean. Give your win-loss analysis the best chance of being successful by focusing on either:

  • A specific customer segment (industry, location, company size);
  • Upmarket or downmarket opportunities;
  • Your main competitors 

Getting leadership and internal stakeholders to buy into the value of win-loss analysis

Get in front of key stakeholders from several different functions and ask them what they’d like to see from a win-loss analysis — and mine them for their suppositions about why their teams win or lose a deal. 

Set expectations regarding when and how you will deliver the results of the win-loss analysis and make sure to address their initial questions. 

If you can, call in a favour with senior leadership and request that they send out a memo to everyone about your win-loss analysis program taking place. 

This will set the expectation that your win-loss program is coming down the pike. It’s also an opportunity to hammer some vital messaging regarding your program:

  • Learnings from win-loss analysis will help every department compete more effectively
  • There are no wrong answers — all opinions/hypotheses/hunches are welcome

Asking intentional, well-crafted questions

The smartest person is not the one with all the answers, it’s the one who asks the best questions. And the best win-loss programs are the ones with the best questions.

Of course, what constitutes the ‘best’ questions will vary case-by-case. But, your questions need to be concise and open-ended. The latter being especially important as the goal is to have interviewees expand on ideas and thoughts, as opposed to providing a short yes/no answer. 

Sample Questions:

  • What was the biggest consideration driving your decision-making?
  • Who was involved in the decision making process?
  • Why was now the right time to make a buying decision?

Distilling results into broad themes and categories

Surfacing specific actionable insights can only occur after you’ve taken a step back and looked at the broad themes that came out of your win-loss interviews. 

We all want to cut the line and communicate those juicy nuggets immediately. But successful win-loss analysis always involves looking at the data from stakeholder interviews and pulling together 3-5 broad themes before getting into the nitty-gritty details. 

Key considerations:

  • Messiness is okay — pulling together disparate pieces of information is hard; start with broad categories and refine from there
  • Let the info sink in — simmer on the results of your interviews for a few days before diving in
  • Not every finding will be a game changer — it’s okay if the findings reinforce existing notions as opposed to surfacing new ones

Communicating the findings in a consumable and actionable way

Once you’ve organized your findings it’s time to package the findings and distribute them. 

Often, the best way to do this is to meet with a group of collaborators with a vested interest in the key takeaways. Some groups to consider are:

  • The C-Suite
  • Sales leadership
  • Product marketing
  • Product management
  • Sales enablement
  • Customer Success

There is a certain amount of tact necessary in sharing findings. One way to do that is by framing the takeaways as considerations versus prescriptive directions. 

“Invest in better CRM platform”


“What tools can we look at to better support our CSMs?”

One thing is clear: collecting and compiling a bunch of great data stemming from win-loss analysis isn’t an end unto itself. The data needs to be communicated in an effective way.

When this is accomplished in an operationalized manner, it lends credibility to your win-loss analysis program and leaves people wanting more. If the foundation is lacking, you might be a one-hit-wonder. 

This is something Clara Smyth, Sr. Director of Product at Slack, has observed from time to time. 

“Once you get some rich win loss data and understand what plays are working in market, what’s resonating with customers, guess what? Now you can move the needle on demand generation campaigns. What I see is that some competitive programs like to dabble. But if you don’t do great market analysis and don’t do it well foundationally, all the other pieces will start to crumble.”

Now that you’ve got the concept of win-loss analysis, the benefits of win-loss analysis, and had an overview of the most important components, it’s time to dive into:

  • Gathering the right interview candidates
  • Establishing interview logistics
  • Compiling a list of questions
Competitive Enablement Show Nailing your next win-loss interview

Catch Ryan Sorley breaking down how to nail your next win-loss interview on the Competitive Enablement Show. Listen on Spotify and Apple Podcasts or watch on Youtube

Deciding who to interview for your win-loss analysis: internals and externals

Most of the win-loss analysis benefits come from external stakeholders — prospects, buyers, current and past customers. 

This is true not only because customer acquisition and retention are what drive business, but also because you’re more likely to get an objective (or at least outside) perspective on your organization from external stakeholders. 

However, internal stakeholders play a pivotal role in the success of your win-loss analysis program — especially in the preparation phase. 

Internal stakeholders 

Your best bet is to form a small group (4-8 people) of internal stakeholders whose functions touch the objectives of your win-loss analysis. Functions like:

  • Sales and revenue
  • Sales enablement
  • The C-suite
  • Product marketing
  • Competitive intelligence
  • Product management
  • Senior leadership

Tap on one key member from each of these teams and leverage their knowledge to build your hypotheses, refine the scope of your win-loss analysis, and start brainstorming questions to ask interviewees. Not to mention spread the word on the benefits of win-loss analysis. 

Moreover, this group of champions can be a great source of support when it comes time to distribute the results of the win-loss analysis. (Bonus points if one of these champions can be a member of the executive team.) 

Choosing the right external stakeholders 

Your main targets will be buyers/customers and prospects — that much is obvious. 

Deciding how many to reach out to, the right wins versus loses split, when to reach out, and whether or not to offer an incentive takes a bit more finessing. 

Invitations to interviewee ratio should be at least 3:1

Even the best parties don’t get a 100% attendee rate. To hedge against a low RSVP percentage, you should plan on sending out at least 3x more invitations than your interviewee subjects. 

Of course, an even higher ratio wouldn’t hurt. 

And make sure you’re sending invitations to whoever made the ultimate decision about the deal being a go or a no. They will have the most intimate knowledge within the best context. 

Ryan sorley CEO at DoubleCheck Research

Aim for a 2:1 ratio of losses-to-wins

There’s an old adage that you learn more from losing than winning. Were that the case, there would be a serious rebranding effort turning win-loss analysis into simply loss analysis. 

If you ask Ryan Sorely, CEO at DoubleCheck Research, he’ll tell you that some of the best competitive intelligence comes from win interviews, not just the losses. As he put it on a recent episode of the Competitive Enablement Show

“A lot of folks will go into win-loss interviews programs and they’ll say, ‘Well, I just really want to know why we lost’. And it’s not a loss program, it’s a win loss program. There’s a huge competitive intelligence benefit to going after the wins, and people often just overlook them.”

In reality, if you find yourself in a situation where you’re working to get company-wide buy-in to your program, you may have to lean more towards deals lost than deals won. That’s why you should aim for a win-loss ratio of 2:1. 

Reach out within five weeks of a deal closing or falling through

On top of making sure you’re interviewing the decision-maker, a second critical consideration is making sure you’re conducting the interviews in a timely manner. 

That’s because the most valuable competitive intelligence will come from those who were closest to the deal — in both time and proximity. 

Offering an incentive to interview subjects

Time is precious and needs to be respected. While the concept of offering an incentive to interview participants is often hotly debated most pros are in favour of it. 

For example, gift cards as incentives are common. You could also consider making a charitable donation on the participant’s behalf. 

Take a social-media dive into the person(s) you’re looking to interview and see if you can connect the dots between one of their interests and a charitable organization. 

Nailing down the logistics of your win-loss interview

Now that you’ve determined the ‘who’ of your win-loss interviews, it’s time to move onto the ‘when’, ‘where’ and ‘how’

Preparing and setting expectations for your win-loss analysis

Since you’ll be leaning on the support of both internal and external stakeholders, you’ll need to be mindful of their experience as well. 

The best way to ensure a smooth experience is by setting clear expectations and preparing beforehand. 

Reaching out to potential interview participants

Get clear on how the actual outreach will occur:

  • Who will be reaching out?
  • How many emails will you send and at what cadence? 
  • When will you follow up by phone?

Interviews should take place in-person or over the phone

Over the phone and in-person interviews are the gold standards of qualitative research. The findings of your win-loss interviews will be simply less impactful if you send an online survey. 

Interviews should be a half-hour at most

Set the expectation that the interview will only take up 30 minutes of time. If you can ask all the questions you need in less time, even better. 

You’re more likely to get favourable responses when asking for a smaller amount of the prospect’s time. 

Send an online pre-interview survey beforehand

Once you’ve got the participants’ confirmation, send them a short questionnaire ahead of the interview.

You can then set the expectation that this short survey will help streamline the interview process and value their time. 

And, as Ryan Sorley touched on in the Competitive Enablement Show’s recent Live AMA, pre-interviews are a major win-win. 

“We call it a pre-interview survey and we position that as, ‘Hey, listen, we want to optimize the time with you.’ In reality, it’s an advantage to both of us because it really gives us a lot of interesting insight up front.”

Let your internal team know when they can expect results from your win-loss analysis

However you decide to distribute your findings, it’s important to set expectations regarding timing. 

Set yourself a hard deadline for distribution, tease the release a couple days ahead of time via your internal messaging channels, and make yourself available to key stakeholders — and the organization at large — to help answer any outstanding questions. 

Coming up with the best Win-Loss Questions and setting the right tone

If you’ve found yourself googling “best win-loss interview questions”, you’re surely not alone. 

But you risk missing the forest for the trees by focusing too much on crafting the right questions. 

The success of a win-loss analysis interview depends more on the tone you set, and how you ask the questions. (We’ll set you up with some killer questions as well though!)

Setting the stage for a free-flowing conversation

An interview is not an interrogation — the interviewee should never feel like they’re under pressure to deliver. 

On the contrary, it’s your job as an interviewer to set a casual, comfortable tone in which the participant feels comfortable with sharing whatever’s on their mind. 

The key word here is ‘flow’. Let the art of conversation dictate the interview, and then follow up on interesting tidbits to dive deeper. 

Having a long list of questions and checking them off one-by-one is a sure fire way to tank your win-loss interview. 

Ask open-ended questions — but not too open-ended

As we laid out in our seminal Competitive Objection Handling 101 article, asking open-ended questions will yield the most useful information whether your goal is win-loss analysis or overcoming common objections. 

That is to say, make sure your questions incite discussion and conversation instead of leading to a dead-end.

open-ended questions for win-loss analysis

One note of caution: as much as we are obsessed with open-ended questions, there is such a thing as a question that is too open-ended. 

In other words, your questions should be tangible and directly related to the buying experience. This is not the time for abstract and philosophical discussions. 

If you find interview participants need clarification on your questions (i.e. ‘what do you mean by that?’) you will need to refine them. 

Start with some softball questions to make them feel comfortable

Use the first few questions of the interview to establish a connection with the participant. This will put them at ease and allow you to build toward more thought-provoking questions later on. 

Then, ask them about their role and how they were involved in the decision-making process. But also take the time to ask a bit about their career history, where they’re from, and anything else you see fit to break the ice. As Ryan Sorley put it:

“You want to let them know that you’re excited to be there…you’re excited for their feedback, make them feel good. Let them know that you know them because you’ve done the homework: you’ve looked at their LinkedIn profile, you’ve gone to their company website. You have a good understanding of them and then you want to start to get them to talk about themselves.”

After you’ve established a rapport with the interview participant, you’re in a good position to start digging deeper.  

Align your questions with the objectives you set for your win-loss analysis

Are you wanting to gather insight on your product or company’s perception in the market? Competitive intelligence on your main competitors? What value propositions are resonating most with buyers?

Whatever your objective is, your questions need to be aligned to that end. 

If it’s understanding the perception of your company in the market, you might ask:

  • What initially attracted you to our company?
  • Who do you see as the biggest players in [industry]?
  • How do you feel our company is perceived from an outsider perspective?

The look and feel of win-loss analysis questions will be the same no matter the objective, but it’s essential that you guide the interviewee towards answers that ultimately provide the kind of actionable insights you need to make your win-loss program a success. 

Ask questions that touch on the entire buying process

The entirety of the buyer’s journey is pertinent to what you’re looking to achieve in a win-loss analysis. 

Of course, keeping your interview to 30 minutes or less is more important than getting into the weeds on every single aspect of the journey. 

Categorizing your questions is one way you can make sure to touch on each part of the journey without spending too much time on one aspect of it. 

Collecting interview data, drawing insights, distributing and acting on the findings

Compile the data into one central source of truth

Help yourself more easily sift through the tens of thousands of words you’ve collected through your win-loss analysis interviews using a transcription app like Gong or Dovetail, and feed that information in your competitive intelligence platform. 

This will allow you to surface recurring themes and data points that you can sort into the three to five broad categories we mentioned at the beginning of this article. 

Narayan CEO at Iceberg IQ

Keep your main objectives in mind when drawing insights 

There’s no magic bullet here. You’re going to need proper analysts who can look into disparate pieces of data and pull out insights that will be valuable to share with a broader audience. 

Finding the most valuable insights is often why companies turn to third-party firms like DoubleCheck Research and IcebergIQ to conduct their win-loss analysis. 

Key considerations when looking for insights

  • Keep your initial objective in mind
  • Keep an open mind to the findings — good or bad, you’re learning
  • Don’t expect every insight to be earth shattering 

Stagger the distribution in phases

When done correctly, the findings from your win-loss analysis can positively impact every function in the organization. 

Depending on the findings however, you will likely not want to broadcast them to the entire company all at once. Instead, start with some key stakeholders in each function, and/or senior leadership. 

For Natasha Narayan, CEO at IcebergIQ, the step of first running the findings by stakeholders is an essential part of a successful win-loss analysis program.

“Make sure you’ve got the key leaders in that room and that each leader knows exactly what’s relevant for them from the feedback. Then, allow time during that meeting so that all leaders are in agreement about what’s important for us to action and prioritize.”

Discuss your interpretation of the insights with them, give your recommendations on how to communicate the findings and next steps, and align on a communication strategy based on how you want the win-loss analysis to be acted upon. 

Turning win-loss analysis findings into your competitive advantage

Following the best practices laid out in this article will set you up with rich, customer-centric data that can help you better position your company, improve your sales process, improve your product offering and much more. 

However, how you decide to assess the data and implement the findings will depend on myriad factors — there is no one-size-fits-all approach. 

But with the right approach, starting with a clear objective and a few work hypotheses, followed by identifying the best interview participants, creating an environment for free-flowing conversation using open-ended questions, capturing the data in one place, gleaning insights as a team, and thoughtfully distributing them, you’ll have everything you need to make the kind of adjustments that help differentiate you from your competitors. 

One thing is for certain: a company without a win-loss program is a company at risk of falling behind their competitors. 

Don’t be one of ‘those’ companies. 

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