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The Practical Way to Perform Win/Loss Analysis

16 Min
Wins and losses review


A win/loss analysis is a great way to evaluate your product and sales process in a clear and  impartial manner. There is no better way to gauge where you stack up against the competition, whether your marketing points are landing with your ICP, or if you’re conveying your USP effectively. Win/loss analyses are a gold mine of valuable information, yet fewer than 20% of companies perform them

In this article we’ll:

  • Explain what a win/loss analysis is
  • Give you practical tips on performing it the right way
  • Demonstrate why it’s so useful

What is a win/loss analysis?

A win/loss analysis in sales is a meeting where the outcome of specific handpicked deals is discussed, usually by the sales team and leaders. Sometimes, product managers, marketing managers and account executives whose deals are being discussed are also present in the meetings. The goal is to learn from these deals. Both wins and losses can be used. 

When done right, a win/loss analysis can help improve product features, conversion rates, win rate, team efficiency, and more. Sales leaders can use these meetings to improve the entire sales process, coach their reps, gauge which USPs are most important to the customers, and what might be lacking in product features.

Going even further, these meetings can reveal problems brewing beneath the surface and help improve the numbers moving forward.  While analyses can be extremely valuable, but you need to pick the right deals to extrapolate actionable insights and the meetings need to be conducted the right way.  The question is how? That’s what we’ll explain in the next few sections. 

How to Pick the Right Deals for Analysis

Picking the right deals for win/loss analyses will set the right context for the meeting. To make it practical, the deals should conform to certain characteristics, such as: 

  • Deals should involve your ICP – this way, you’re excluding peculiarities and outliers, which makes it easier to focus on trends and important changes
  • Deals should have a significant ACV (annual contract value) – the reason for this is you want to focus on deals that are significant wins or losses for your organization
  • Deals have to be closed (won or lost) – you want these deals to represent your entire sales cycle so you can get a look at the big picture
  • Sales leadership should pick the deals – the sales leaders should have a good understanding of the deals. They should be able to choose useful deals for analysis

Picking the right deals will be the difference between a useful win/loss analysis and a meeting that’s wasting everyone’s time. The wrong deals may send you on a wild goose chase at best and ruin something that’s working at worst. 

Choosing the right deal and gathering useful data will ensure that doesn’t happen. You can always count on data to show you the full picture. 

Who is Responsible for Picking the Deals? 

Generally, top sales leadership is responsible for picking the right deals. They often heed the recommendation of first and second line sales manager and in some cases, even the AE’s.

One of the main motivations in choosing a certain deal is so that it can showcase the challenges your organization is facing. Sales leadership is well aware this adds value by either demonstrating those challenges so they can be addressed in the future if the deal has been lost. Or by showcasing how the challenges were overcome.

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What Kind of Data Should You Gather?

Data is an essential part of every practical analysis and in/loss meeting is no exception. Data will provide legitimacy to the claims and make the review more objective. Here’s the data you will need to perform the analysis properly.

Sales activity

Sales activity represents the actions of your reps during the sales cycle. It typically includes:

  • Calls
  • Emails
  • Meetings
  • Demos

Sales leaders need the sales activity to evaluate the process for the win/loss review. They can use it to draw conclusions about the effectiveness of the sales process and the sales reps. This is the quickest way to reveal whether reps need more training or if there’s a need to change to the sales process. 

While sales activity is no doubt valuable, the perspective of your reps only gives you half the picture. To see the other half, you also need to gather data on the side of the prospects. 

Prospect details

The prospect details will show if your reps contacted the right people or not. The data will add more context to the deal. Here’s the relevant details you need on the side of the prospect:

  • Name and title of the person contacted
  • Company size
  • Pipeline point of entry (opportunity source)
  • Problem your organization attempted to solve

This data will give you a better look into who the prospect is. It might allow for additional insights into the deal outcome. 

To gather all this data, you need excellent CRM functionality and meticulous data entry. Of course, there are also easier solutions. Intuitive software systems like MoData can be easily integrated with your CRM and keep track of all of this (and more).

Prospect feedback

After getting the prospect details, it’s a good idea to try and arrange a feedback interview. The goal of the interview is to determine: 

  • Why the prospect contacted your organization
  • How they heard about you
  • What need caused them to
  • What did and didn’t work for them in your marketing and sales process
  • What ultimately informed their decision to work or not work with you

Prospect interviews are the best way to receive direct feedback for your sales and marketing process. They allow you to identify common weaknesses in your approach. It’s important to make the interview standardized if you want to extract any real value. Adding prospect answers to the data will allow you to dive deep into the issues that may be brewing beneath the surface.

How Much Time Should You Spend on Win/Loss Meetings?

Even though win/loss analysis for every chosen deal is useful, you need to put in some time constraints in order to keep people on topic. We all know how easily sales meetings can spiral out of control and win/loss analysis is no exception.

You can make it an hour-long meetings and discuss 3-4 deals per meeting.

Usually, 15 minutes per deal should be enough. 10 minutes for presentation and setting the context, and 5 minutes for deliberation. We would highly recommend an AE to present the data and details about the deal as opposed to sales leaders (more on this below). The sales leaders and the team should then deliberate on the details and discuss the reasons why they think the deal was won or lost.

In order to make sure it’s easy for everybody to fit within their 15 minutes, every deal review should follow the same template. This will eliminate confusion and will make things easy to follow. Once people are familiar with the format, this is an extremely efficient way to conduct these meetings.

You should always leave 10 minutes at the end for Q&A and closure. Finalizing the meeting with a Q&A session will allow you to:

  • Summarize your findings
  • Plan for ways to improve
  • Relay the information to the other stakeholders

Why Should AEs Be Involved? 

Many organizations consider Win/Loss reviews to be a sales management discussion, precluding AE out of the loop. Even if they are part of the meeting they don’t get to (or at least not encouraged to) participate actively. 

This is a big mistake. It’s highly recommended to allow the AE, who owns the deal being discussed, to lead most of the first 10 minutes of discussion. This allows: 

  • AEs to provide full context. It adds the requisite color and background other participants  can get only when they hear it from the proverbial “horse’s mouth” 
  • Presenting in such meetings helps AE’s a lot.
    •  If they are good it helps boost their confidence and give them the highly motivating visibility in front of a broader audience beyond sales, which often includes CXOs.  
    • If they are not good, it provides a great insight into training opportunities for such AEs. Let’s look at it this way, you would rather have them fail in from of internal audience than in front of prospects /customers, right? 

If you are too worried about your AE’s making big mistakes and wasting everybody’s time, it’s often advised to have a “pre-meeting” with some sales team members. This meetings allows you to ensure the message the AE’s presenting is to-the-point. Added bonus is the AE gets a dry run to calm the nerves down a bit. 

How Often Should You Conduct Win/Loss Analyses?

Now we are clear on the recommended length of these meetings, but what about frequency? How often should you conduct a win/loss review? 

This would depend on the average length of your sales cycle. The longer your sales cycle, the rarer these meetings would be because you need valuable data and appropriate deals for review. That being said, at least once per quarter is a good guideline. However, don’t put too much emphasis on frequency. The important thing is to make sure these analyses are useful.

Don’t Forget to Review your Wins!

You learn as much from your wins as you do from your losses. So make sure you include some winning deals in the review. Follow the same general pattern, but this time focus on reasons why you won. 

While summarizing at the end of the meeting, juxtapose the reasons why you won with the reasons why you lost. See if something pops and you find an answer to the question “why you lost”. 

You would typically discover that one part of the sales organization is already employing some of the techniques your review concluded are winning techniques. This will be the difference between those who win and those who lose. Once you identify good practices in the analysis, double check with your high win-rate reps. You’re ought to discover they’ve been employing these practices all along.

It’s much easier to cross pollinate than to introduce new ideas in the sales team. Don’t miss the cross pollination opportunities by not reviewing your wins.  

Also, talking about wins is pretty fun!

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How to Make the Win/Loss Analysis Useful

There is more to a win/loss analysis than gathering the data and talking to the prospects. To make it truly useful, you need to be practical.

Allow the sales rep or AE present the deal and its details. Double check with the data to make sure any subjective bias is eliminated.

Next, discuss the deal and try to identify specific reasons why it succeeded or why it failed. Some common reasons for failure include:

  • Pushy sales reps
  • Discrepancy between perceived value on the side of the customer and actual value
  • Product or service does not fulfill customer needs
  • Over-promise and under-deliver – marketing makes promises the organization can’t deliver on

During the Q&A, try to identify trends and document them. By the end, you should have a pretty good idea what works and what doesn’t. 

Based on those findings, formulate a plan to fix recurring issues. And remember: do not make win/loss reviews a blame session – it’s a coaching moment that should help your team grow. 

Win/Loss analysis can be great for:

  • Determining any gaps between you and your competitors. Better features, easier installment, technical execution or lower prices – it’s a good idea to know where you stand in this regard.
  • Validating assumptions about your product. It’s a good idea to know if al the assumptions you make about your product have any real basis.
  • Creating a culture of transparency. Failures are inevitable and they need to be discussed, not swept under the proverbial rug. Being transparent about both wins and losses is vital for the development of the organization. It allows both to celebrate the wins and learn from the losses.
  • Checking if your marketing is landing with the right audience. Win/loss analyses are mostly associated with sales but that doesn’t mean they can’t be valuable to marketing.
  • Determining the quality of the qualification process. If it turns out too many deals are lost because they were qualified at an earlier stage when they shouldn’t have, then you have a qualification problem that needs to be taken care of.
  • Strengthening the connection between Sales and Marketing. Lack of communication between these two departments is a critical problem which win/loss meetings helps you to address.

These meetings can be extremely beneficial all around.  


Win/loss analyses are a great way to identify problems in your organization, strengthen the connection between marketing and sales, and improve your sales process. Very few sales organizations perform them well, but those that do it in a practical way can only win from the experience.

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