Win Loss Analysis

Win Loss Analysis is one of the most powerful tools in the Revenue Enablement toolset and should be considered part of standard best practices for any organization.

We have had several conversations about this process, including:

These conversations and others, combined with personal experience, have led to this article on win-loss interviews.

In this article, we will cover:

  • What is a win loss analysis
  • Why do you need win-loss analyses
  • How do you build and run an effective win-loss program
  • How do you leverage the lessons learned

If win loss interviews are not yet part of your standard go-to-market motion, read on and incorporate these into your continuous improvement efforts immediately.

Win loss analysis is a powerful Enablement feedback loop.

What is a win loss analysis

The win loss analysis is a post-decision interview step that should take place for any closed deal, whether it was won or lost by your sales organization.

During this review step, all key stakeholders in the deal are brought together. This includes meetings with internal teams and a separate conversation with the decision makers from your prospective buyers when possible.

Why do you need win-loss analyses

The win loss analysis provides you with valuable information, including:

  • Competitive Intelligence
  • The decision process your buyers use
  • Potential improvements to your discovery process
  • Why do you win and lose
  • Content and training gaps
  • And… So much more.

As an example, in his interview with Britta (noted above), Cian Mcloughlin shared many of the loss reasons he has seen through loss analysis interviews, including:

  • Failure to listen to the customer.
  • Failure to fully understand the needs of the customer.
  • Sales reps showed up and started pitching.
  • The seller was not professional.
  • Content is boring, generic, and bland.
  • Your company or team feels risky.
  • Your sales team made no attempt at relationship building with key members of the buying team.

Individually, any of these will make it a challenge to meet your sales goals. When you have multiple of these issues taking place, you will lose a lot of deals.


Without a win-loss analysis program, you have no idea that these issues are impacting your close rates.

How do you build and run an effective win-loss program?

If I did not already convince you to do win-loss research, you probably have already jumped away from this article. Since you are still here, I’ll assume you’ve bought into the ability to get better results from this program.

So, how do you get started?

In an ideal world, you would review every single deal that closes (won or loss) as soon as it happens.

Since none of us live in that world, let’s talk about starting your program.

Define your WHY

Why are you going through the process to set up a rigorous win-loss analysis program?

Are you primarily focused on gathering insights about your competitors to give you a competitive advantage?

Are you trying to understand specific reasons why your win rate is not as high as you need it to be?

Are you seeking to gather actionable information for your product teams to explain gaps in key product capabilities?

Whatever your reason, ensure that all members of the revenue organization are on board with the critical purpose.

Determine what cadence you can support

You will spend at least one hour with your internal teams and, hopefully, another hour doing buyer interviews for every deal you analyze.

Based on your volume of deals and the number of resources you have available for this function, resource allocation against all tasks, you will come up with a magic # of opportunities upon which you can perform this analysis.

In many cases, your Revenue Enablement team will only be able to dedicate 5-10% of their time to this activity.

Define a process for determining the deals you will analyze

For most businesses, it is not feasible to run every opportunity through this analysis. To keep the process manageable, begin the process around the contract stage of your sales process. To determine the right time for your business, sit with your Revenue Operations team, as they will tell you the exact timing based upon how your company operates.

How do you prioritize your deals?

Let’s step back and review our WHY.

Based upon the top priority for the program, define a decision-making process to identify those deals most appropriate to analyze.

Based upon this framework, ask your Operations team to set up an alert in your CRM system for deals reaching this stage.

And then…

Identify the people to speak with

When an opportunity reaches this stage, you want to reach out to your prospect’s internal stakeholders and the buying team.

Your internal team

Based upon your WHY, you may want to include only the sales team members who participated in the deal; you may wish to have product management, product development, customer support, or countless other teammates.

Assemble this team, ensure they are clear on the purpose of the interview, and give them the list of questions you will be covering ahead of time so they can prepare.

Example questions are below.

Your prospective buyer

You will encounter resistance from your sales team when asking to talk to the prospective buyer, especially in a lost situation.

However, if you can overcome this resistance, have your sales lead for the opportunity reach out to their customer contact and get written confirmation that when the deal closes, they will sit with your Enablement team to review the agreement.

How you reach out is as vital as when you reach out.

The best way is to ensure the customer understands that you are not trying to force them to second-guess their decision or point out flaws in their decision-making process. Your goal is to learn and improve how you, as individuals and organizations, work with prospects. These conversations are about helping you get better.

What questions should I ask during the win loss analysis?

What is the customer buying process?

Review their buying process from the time of problem awareness through the final signature. This should include building an understanding of:

  • What steps did they walkthrough?
  • Who participated at each stage of the process?
  • What role did each involved person play?
  • What were the key concerns each person brought to the decision?
  • Was any internal buying checklist built out? Can you get a copy of these?

What vendors did they check out?

You are never the only vendor in the mix; who else did they evaluate? For each vendor:

  • What did they like about a specific vendor?
  • What did they dislike?
  • Where did that vendor outperform you?
  • Where did that vendor fall short?
  • What pricing did you end up paying?

Get their permission to follow back up with them if you have additional questions.

Use these conversations to remind the customer of why you are so awesome. If you lost the deal, make sure you also ask when you can reach back out to them.

And remember, record these conversations, as long as you have permission, as you will refer back to these.

How do you leverage the lessons learned

As always, go back to your WHY.

The win loss analysis is a valuable tool to obtain actionable insights, but only if the right people are learning from these conversations.

Ensure you have:

  • Defined where the records of all these sessions will reside.
  • Collaborated with key stakeholders on how you will share lessons learned with them
  • Set expectations across these stakeholders as to the outcomes expected.

You will identify many areas of opportunity for improvement through this process. How you prioritize and manage these will ultimately define if this process is a success for your business (or not).