Trust Enablement

Improving Sales Performance with Enablement Recruiting, Consulting, Outsourcing, Coaching, and Insights on Strategies, Tactics, and Tools

Win Loss Analysis

An effective win loss analysis program will lead to continuous improvementThe win loss analysis is one of the most powerful tools available to a company to understand why their customers chose to buy from them. And to learn why the deals the lost when to the competition.

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, and conduct win loss analysis
  • How do you leverage the lessons learned

If win loss analysis and interviews are not yet part of your standard go-to-market motion, read on and incorporate these best practices into your business now.

What is a win loss analysis

The win loss analysis is a post-mortem of your performance over the course of a specific opportunity. The win loss should be performed for both opportunities you won, and those you lost.

And if you have to prioritize, focus on the competitive opportunities first as the feedback from those will provide tremendous value.

If you need further prioritize, focus on the lost opportunities first, as the feedback from these deals may provide you with findings that are faster to implement.

Why do you need win loss analysis

The win loss analysis provides you, post decision with valuable business insights, including:

  • Competitive Intelligence
    • What can you learn about your competitors products?
    • How is the competitor coming across compared to your team and your solution?
    • What insights can you learn about how those companies are discussing your company?
  • The decision process your buyers use
    • Are you missing content to support the deal for a specific persona?
    • Is your understanding of the industry outdated or simply wrong?
    • Did you fail to spotlight a key service, important benefit, or important data that would have convinced the prospect to go with you?
  • Potential improvements to your discovery process
    • One benefit from the deals you lose is that you discovery questions you should have asked. Take action on these learnings!
  • Why do you win and lose
  • Content and training gaps
  • Related to the above, maybe your technology is simply not as good as that of your competitors. What do you need to improve?
  • Are your teams following the sales process? Perhaps they failed to update the CRM with relevant data.
  • Perhaps your team is not bringing enough industry insights and research during specific conversations with key stakeholders. Your customers, and the prospects you lost, may be able to shed a light on this.
  • And… So much more.

As an example, in his interview with Britta (noted at the bottom of this article), 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 instead of listening to the client.
  • The seller was not professional, they conducted the meeting in a fashion inconsistent with how the prospect works.
  • Content is boring, generic, and bland.
  • Your company feels risky – the prospect was worried you would not be around in the future.
  • Your sales reps made no attempt at relationship building with key members of the buying team.

These findings would destroy your ability to win competitive opportunities. How many of these problems are showing up with your sales and marketing teams?

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

Your win loss analysis program is the critical feedback loop you need to improve upon your performance now and into the future.

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

If I did not already convince you to do win loss analysis and 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 by taking time to learn from your wins and losses.

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.

We mentioned above how you could prioritize — let’s go a bit deeper now

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 gathering data you can’t find from your CRM to research why you lose more deals than you are winning?

Have you heard feedback that your technology is behind? Maybe your solutions and services are not delivering the needed ROI for your customers?

Are you concerned that the resources your marketing team is providing on your website, or to your sales organization, are not convincing prospects to move opportunities forward?

Perhaps you are in a crowded industry, and struggling to articulate the benefit of working with your business versus your competitor.

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

Determine what cadence you can support

You will spend at least an hour with your internal teammates and, hopefully, another hour doing buyer interviews for every deal you conduct win loss interviews against.

Based on your volume of opportunities and the number of resources you have available for the win loss anaysis, resource allocation against all other tasks, you will come up with a magic number of opportunities you can expect to review.

In many cases, your people will only be able to dedicate a fraction of their time on this vital business process.

Define a process for determining the deals you will analyze

We have hammered on the need to prioritize what you analyze based upon the volume of opportunities and the resource made available for win loss analysis.

How do you prioritize your deals?

Let’s step back and review our WHY.

Based upon the top priority for the program, define a simple rubric to calculate a score for each possible deal, then start at the top and work your way down the list.

Few organizations will review all deals.

Use your decision-making process to set up an alert in your CRM system for deals matching this criteria.

And then…

Identify the people to speak with

During this review step, all key stakeholders in the deal are brought together. All members from sales and presales, customer success, management, and other teammates need to attend.

Also, have a separate conversation with the decision-makers from your prospective buyers when possible.

Your internal team

Based upon your WHY, you may want to include only the sales team 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 a little further down in this article.

Your prospective buyer

You will encounter resistance from your sales team when asking to talk to prospects, especially in the case of a loss.

However, if you can overcome this resistance, have your sales lead reach out to their customer and get written confirmation that when the deal closes, they will sit with your Enablement team to perform the win loss analysis.

How you reach out to prospects matters.

Ensure the customer understands that you are not trying to force them to reconsider your solution 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 improve.


What questions should you ask during the win loss analysis?


Here are a few example questions for you to incorporate when performing this 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 walk through?
  • Who participated at each stage of the process?
  • What role did each 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 this? How buyers rank and calculate these rankings, is important to understand.

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 competitor?
  • What did they dislike?
  • Where did that company outperform you?
  • Where did that vendor fall short?
  • What pricing did these customers pay?

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 this deal was a loss, make sure you also ask when you can reach back out to them.

Remember: Lost opportunities are simply a deferred sale, nothing is permanent if you stay positive, humble, and respectful with customers.

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

Questions to ask after losing an RFP

In large part, the questions to ask after losing an RFP are the same as losing a deal at a later stage. However, we would add the following questions:

  • Were there issues with specific answers? Do you have a gap in functionality or was the response unclear?
  • Did you take too long to respond? Do you have a process issue?
  • Was this an RFP you should have responded to, or were you simply deal fodder?
  • What is your current RFP win rate for similar deals?

As we noted, the questions to ask after losing an RFP are generally the same as we discussed already — just dig into your RFP response process a bit more deeply.

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).

Check out this podcast episode with Chad Dyar

[buzzsprout episode=’6799876′ player=’true’]

In this conversation, Chad Dyar guided us through what is win loss analysis, how to create a win/loss analysis process, an overview of the win loss analysis questionnaire, and many other aspects of a great win loss analysis process.

  • To do this well, you need to have a tight sales process and clarity of what you are trying to achieve. Try to start the process right around the contract portion of your process, perhaps a bit earlier. This is when your sales team introduces you and gets verbal/written confirmation from your main contact that after the deal is done, win or lose, they will chat with your Enablement team about the deal.
  • The win/loss meeting should be around 30-60 minutes in length and be done with the main contact your seller was working with.
  • At the end of win/loss conversation, get permission to reach back out for follow-up as required.

So, what are the general areas you walk through during these conversations.

  • What was the buying process like? What prompted their awareness of the problem? How did you start looking for solutions to the problem? Who was involved in the buying process?
  • What competitors did you check out? How did you determine who to talk to? What did we do well, our advantages? What did they do well, their advantages?

There are lots of gold nuggets in here — Give a listen and remain curious.