Win-Loss Analysis: A Step-by-Step Guide

by Felix Krueger

The outcomes of a sales conversation can seem very black-and-white.

Outcome A: Your sales team lost the deal.

That's typically when the guessing game starts.

"It's the bad economy."

"Buyers don't have any budget these days."

"They don't like our brand."

If you're lucky, the prospect gave you a one-line explanation.

Outcome B: Your sales team lost the deal.

The assumption is then typically that everything went smoothly (which is most likely not the case). No need to investigate further because the contract has been signed.

If only there was a way to gain qualitative insights into the real reasons why a deal did or did not end up happening. If only this intelligence was available so GTM strategies can be consistently optimised.

If only, right?

I don't have the magic formula for your GTM strategy optimisation but I have something just as good: A Win-Loss Analysis.

In this post, we'll take a detailed look at  what a Win-Loss Analysis is, how to conduct one, what the benefits are, and more.

What is a Win-Loss Analysis

In the simplest terms, a Win-Loss Analysis is a market research approach designed to create an understanding of why deals were won or lost.

The data required for this analysis is typically sourced by conducting an in-depth interview with a member of the buying committee the sales team has interacted with.

The goal of this interview is to paint a picture that is as close to reality as possible considering all facets of the interaction between the buyer and the seller.

Some of the topics covered during the interview in a B2B context would include the following:

  • Brand perception
  • Buyer problem to be solved
  • Solution selection criteria
  • Evaluation process
  • Buying team profile
  • Competition
  • Content resources utilised
  • Perception of price
  • Sales interaction

When to Conduct a Win-Loss Analysis

A Win-Loss Analysis should be conducted as often as feasible with the given resources to identify market patterns and trends. It is typically conducted with a set number of clients or prospects each month who have entered the Deal Won or Deal Lost stage in the CRM. The outreach to organise an interview with a buyer should then happen as soon as possible after a decision has been made. 

How to Source Win-Loss Analysis Interview Partners

The person or team responsible for conducting interviews should work with the sales leadership team on identifying new accounts that have been added to Deal Won or Deal Lost stages in the CRM.

Once the potential interview partner has been identified, the highest response rate can typically be achieved when an Account Executive with an existing buyer relationship reaches out.

When reaching out, it is crucial not to come across as threatening and to reemphasise that this is a market research activity designed to help the business improve. 

Negative Perceptions to avoid when reaching out to Win-Loss Analysis interview partners

  1. 1
    It is not an attempt to make the prospect re-enter the sales conversation
  2. 2
    It is not an attempt to catch a salesperson doing the wrong thing
  3. 3
    It is not an attempt to identify flaws in the client's/prospect's decision-making process

From experience, clients that have recently signed a contract will be more likely to collaborate because they had a positive experience and are excited about working with your business.

If there is a budget, I would in each case recommend offering compensation for the interview partner's time. A common offer is a $200 Amazon voucher for a one-hour interview. This is an attractive incentive for the buyer and offers great ROI for your business if you consider the benefits that come with the insights you'll gather.

It is important to note that the term Win-Loss Analysis might not mean anything to the buyer you'll contact as this term falls into the category "office use". "Market Research Interview" is a term that might be more descriptive to potential interview partners who don't have a B2B sales background. 

How to Reach out to Potential Interview Partners

As with any outreach activity with existing contacts, picking up the phone is the most effective way to get an immediate response and lock in a time for a meeting.

The first go-to option should therefore be the AE calling the client/prospect to share some high-level information, ask if she is interested in participating and lock in a meeting time with the interviewer. 

Outreach Call Script

Hi, this is [AE NAME] from [BUSINESS NAME].

I'm following up on our recent conversation around [PRODUCT NAME].

Because we're always keen to be as helpful to our potential customers as we can we conduct market research interviews with people like yourself who have recently interacted with our sales team.

Some of the things we explore in these interviews are your perception of our organisation, your decision-making process, and how we could make our product more useful to you.

IF DEAL LOST: This is not an attempt to change your mind but purely market research that will help me and my colleagues improve.

IF DEAL WON: This is purely a market research initiative that helps us understand what we did well and where we can improve.

Because we know how valuable your time is we would like to offer you a $200 Amazon voucher for an hour of your time.

Would you be open to an interview with my colleague [FIRST NAME]?

IF YES: Great, when is a good time for you? I won't be attending the meeting but I'll send you an invite right away to secure the time slot. [Send calendar invite with call details]

IF NO: That's OK, I completely understand. Can you think of anybody else who played a key role in the decision-making process who might be interested in participating in this market research interview in exchange for a $200 Amazon voucher? 

[If the potential interview partner agrees to participate, it is important to arrange a time on the spot. Make sure that the person calling has access to the calendar of the person conducting the interview. Any additional step in coordinating the meeting reduces the likelihood of it happening.] 

How to set the Interview up for Success

Once the meeting has been arranged, two key issues are most likely to occur. 

  1. The meeting is cancelled last minute or the interviewee doesn't show up
  2. The interviewer struggles to put the interviewee at ease during the interview and only receives short answers

To set the interview up for success, the interviewee needs to be introduced to the interviewee. This is an attempt to build rapport early and position the interview as less transactional. If both of these goals are achieved, the two key issues mentioned earlier are less likely to occur. 

The introduction should look something like this:

Introduction Email Template

Hi [Interviewee First Name],

Please meet my colleague [Interviewer Name].

[Interviewer First Name] will catch up with you [meeting date] for the interview. The call details are attached to the invite I have sent you earlier.

Thanks in advance from our entire team for participating in this exercise and giving us the opportunity to improve. 

Kind Regards,

[AE Name]

The interviewer should then follow up with a friendly email to make a positive first impression and to build rapport. This can be combined with a LinkedIn connection request. 

Follow-Up Email Template

Hi [Interviewee First Name],

Great to meet you and thanks for participating. I'm looking forward to our catch-up. 

Kind Regards,

[Interviewer Name]

It might seem trivial but with this sequence, we've seen attendance rates and interview quality improve dramatically.

The Questions You Should Ask During a Win-Loss Analysis

Structure is key to maximise the time available with the interview partner.

Below is a list of questions you should consider covering in your interview. These are of course just a guide as you might want to focus on particular areas by asking follow-up questions.

Buyer persona 

What is your role at BRAND NAME?
What are your responsibilities?

Brand perception

How and when did you first hear about us?
What was your perception of us at the start of the evaluation?
How did that perception change by the end of the evaluation?

Business drivers

Why were you looking for a new solution?
What problem were you looking to solve?
What is the (opportunity) cost of this problem to your business?
Why is now the right time for you to take action?
Why was your current solution unable to solve this problem?

Selection criteria

What were your must-have requirements?
Which was the most important and why?
Were any internal buying checklists built out? Can you share a copy?

Evaluation process

How did you go about evaluating providers?
What were the most important moments in your evaluation process?

Buying team profile

Who else was involved in the evaluation process?
Please describe each person’s role.
Who else in your business advocated for this decision and why?
Who in the business was against that decision and why?

Resources utilised

While researching options, which resources did you use?
What resources did you wish you had but didn't?
If you spoke with peer references, what kinds of things did they share?
Which vendor marketing or sales content did you find to be most valuable? What was missing?
How useful did you find our marketing and sales content? How could they be better?


What were the strengths and weaknesses of our solution?
How did you evaluate our solution?
Did you participate in a product demo or trial?
How well would you say our solution aligned with your needs?
Were you given access to our roadmap? If so, is there anything you think we’re missing? And what excited you most about it?


Which vendors did you consider?
What were their strengths and weaknesses?
Was there anything notable that they had but we didn’t?
Where were we stronger than the others?
Is there anything on our competitors’ roadmaps you found appealing?


Who did you ultimately select and why?
What were the three things that pushed you over the edge?
What was the winner missing that you wish they had?
What were the primary reasons you selected/did not select us?
What could we have done differently to have won your business?
Do you feel confident with the decision you made?


How much weight was put on the price?
How did you feel about our pricing?
If price was not a factor, would you have chosen a different provider?
How did our pricing compare with the others you evaluated?


How would you describe your interactions with our sales team?
Did you feel like our sales team understood your pain points and needs?
On a scale of 1-10, how would you rate your experience during the sales process?
What could they have done better?


Would you consider our solution again in the future? If not, why not?
Would you recommend us to others?
Is there anything else you think we should know?

Here is also a link to the template document we use for our clients which contains all of the questions above and allows for notes to be added.

Win-Loss Analysis Interview Template

Free resource

Please select File and Make a Copy to store it in your Drive or simply download it as an Excel file.

If the interview partner agrees, record the conversation so initial notes can be improved after the interview has finished.

This can easily be done in Zoom if the interview is conducted remotely. 

If you meet the interview partner in person, you might want to use an app that records audio on your phone.

After the interview recording is complete, consider creating a transcript using an online service like for your records.

The key benefit of recording the interview is that it will feel more like a conversation. Instead of the interviewer taking notes during the meeting, she can focus on asking thoughtful follow-up questions. In this scenario, notes can be extracted from the recording or transcript after the meeting has finished. 

If the interviewee does not agree to be recorded, taking notes during the conversation will of course be necessary.

How to reap the benefits of a Win-Loss Analysis

The benefits of a Win-Loss Analysis are only limited by the ability to share insights across departments. Generally speaking, any customer-centric organisation should be able to use the insights gathered in customer interviews to either formulate or optimise its GTM strategy and its department-specific elements.

Here are some of the elements of a GTM strategy and associated tactics that can benefit from a Win-Loss Analysis. 

  • Buyer personas
  • Buyer journey map
  • Sales process
  • Sales rep coaching plans
  • Value messaging and positioning
  • Pricing
  • Product development opportunities
  • Content strategy

Over To You

I hope this post inspires you to conduct a regular Win-Loss Analysis for your business and I'd love to know how the intelligence you've gathered has helped optimise your GTM strategy. If you have any questions or encounter difficulties when trying to launch a regular Win-Loss Analysis program, let me know in the comments below.

Connect with Felix Krueger on social media:


buyer insights, market research, sales enablement, win-loss analysis

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