Win loss analysis: How to know exactly why you lost a “winnable” deal

Losing any deal you worked on hurts. All the days and hours that you put into the deal—you thought they’re excited about your product, and then—Bam! The deal is gone! It sucks, doesn't it?

The best of AEs, VPs of sales have been through their cycle of dream runs and lean patches. However, what makes them the best is their ability to be consistent in winning deals, which comes from their continuous learning from every single deal.

We aren’t talking about the same old internal forensics and random reckonings you have heard a hundred times already—”Competitor undercut us”, “It wasn’t apples to apples”, “Someone internally was championing for a competitor.” 

While they sound like perfectly valid reasons—they neither give you clarity nor map to specific moments in the deal. True learning and consequently consistency in winning deals, comes from unbiased analysis of wins and losses based on real deal information. 

Let’s dive into understanding how these learnings can become part of your daily sales workflow!

Understanding where and how deals slip

A lot has changed in SaaS sales since 2022. It’s not “growth at all costs” anymore. There’s been a shift from a sales centric process to becoming completely buyer centric.

As a result, the average salesperson following the old playbook is failing. You need to thread a balance between controlling the narrative as well as supporting the buyer’s process. It’s not either or, anymore.

Failing to support your buyer leads to:

• Indecision: “I don’t get why I need to buy, and how to buy/get this approved”
• Ghosting: “I don’t feel like John is being helpful, I’ll manage…”
• Losing to a Competitor’s rep: “I feel I’m in much better hands with Lindsay, who gets me”

While it feels like you’re doing everything in your control—you suddenly realize the deal that was right under your nose, has moved to a competitor. 

So, where and how to learn what to fix?

The easy answer would be—if you’ve invested in a conversation intelligence tool, start with listening to sales calls, do a win/loss analysis, and invest in sales coaching. But, there’s more to it than just investing in the right tools.

Yes, you want to know how deals are slipping through the cracks and want to prevent it. And you have the tools too.
But can everyone find the answer and fix the leak? No.

Even if you are among the 1% leaders who diligently reviews calls, runs meticulous pipeline reviews, and goes through the notes that reps update in the CRM on every deal that’s lost or won—there’s not much to learn from.

Why?

Because the rep notes on lost deals often tend to be one liners such as:

“Went with competitor X”
“Their priority changed”
“They wanted a barebones cheaper alternative”

And for deals won, the notes are even shorter such as:

“Provided value”

What does that even mean? It gives you nothing!

Since you didn’t get anything actionable or insightful from the notes, you have to go the email trail of each of those deals, and listen through the 5-7 meetings leading up to the final deal stages, to get a picture of how the deal transpired.

And if you have 5 AEs on your team, and let’s say each of them have 5-6 on doing deals at any given time—it’s impossible to get 100% coverage and fix the gaps. Even if you listen to each call at 2X speed, you have to carve out 60+ mins a day to just listen to calls.

So, what’s the solution?

It’s not the reps fault, they have so much on their plate. Ask yourself: Do you have a repeatable and reliable process of analyzing your deal wins and losses.

What is a win-loss analysis?

Win-loss analysis is the process of understanding how your recent prospects and customers evaluated your product or service, and why they did or did not buy from you. 

It’s different in nature compared to a customer survey in both audience and insight because customer surveys only give you the insight into why they bought/subscribed to your product, whereas a win/loss gives you a lot more objective, and detailed perspective because it also throws light into why a prospect chose a competitor over you, or didn’t buy at all.

Win-loss program: What is an acceptable win-loss ratio?

It comes to your sales leadership and the standards you want to set. Because context is king, you might want to evaluate your team's performance based on historical figures in your organization and the current macroeconomic factors.

Even if your team is breaking even in terms of revenue and expenses, an improving win-loss ratio can signal progress, depending on the stage of your business.

How to analyze your deal wins and losses

The strength of a win/loss analysis is highly dependent on win-loss resources, i.e., how well you capture deal information across stages and the feedback loop you build.

Understand your relationship with prospects

New business opportunities come from both net new prospects as well as existing clients. To improve your success rate, it would really help to have a process to collect feedback from existing customers to understand:

1. why they chose you
2. what specifically do they like in your product
3. what you could improve in the sales process

Similarly, net new prospects may be willing to give you insights on their business needs and their perceptions of your brand, if you engage them far enough in advance to create an opportunity.

Continuous risk assessment during the deal cycle

Optimizing your win loss performance needs more than drawing insights about why a purchase decision by a customer. You need to understand the blindspots and potential risks during the deal cycle.

1. How did the meeting go?
2. Are we dropping the ball in terms of engaging the key stakeholders
3. Have we addressed the objections of the prospect well?
4. Are the deal stages progressing?, and more

On that note, here’s our recommended reading on the 5 deal risks you need to be aware during the deal stages:

However, the challenge often boils down to how granular and objective one can get in their analysis and capturing data.

But before getting there, for a minute, imagine asking your customers questions like:

• What product or features were you initially interested in? 
• Was it a good fit from the start? 
• What pain point or problem were you trying to solve? 
• How many people were involved in the decision making process?

Even if your customers gave you time to get on a call—asking the above questions gives them an impression that you have no context about them. Additionally, similar to the CRM notes capturing discussion—a lot hinges on who is capturing the learnings from every deal, how meticulous they are, the sources that they have access to, their rapport with sales people, level of visibility into deals, and more.

One way to standardize and set a quality bar for win/loss analysis and summarization is—automating it using AI.

In fact, Avoma offers AI based win/loss analysis as part of its conversation and revenue intelligence. So while it records your conversations, takes notes, and updates your CRM — it also analyzes your deals to give you a win/loss summary.

And by experience, you’ll see that it does make a massive difference if you were to compare with rep’s notes on win/loss reasons (obviously due to time constraint and several other priorities on their plate).

Here’s a snapshot of one of our rep’s notes on why we won a deal vs. Avoma’s AI summarizing the reasons for winning the deal.

It’s obvious which one gave you a better context, right?

And the best part about this automation is:

As soon as the rep marks a Deal "Closed Won" or "Closed Lost", Avoma's AI analyzes all your meetings, emails, and calls and generates a more detailed response, and automatically updates the CRM fields! 🤩

While technology helps, it’s just the beginning of several new learnings.

For example, let’s say you have a lost deal.

The AI loss analysis summary can be a great starting point for you to drill down into everything that transpired in that deal—listen to all the calls, identify a pattern of pain points or objections (if you see recurrence).

Group them into themes such as:

• Product issues/gaps
• Gaps in the sales process
• Mismatch in expectations, and more.

Once we have a process for capturing the insights on why we won or lost a deal, what next?

Incorporating the learnings into your daily sales workflow

Knowledge for the sake of knowledge is cool, but the ultimate purpose of effective win-loss data and win-loss insights is to improve performance over time. Win/loss analysis gives you the data to validate the things your sales team is doing right and insights into what’s not working. 

In fact, the whole point of automate the win/loss analysis is to enable one or more of the following:

• Improve the effectiveness of your sales strategy
• Improve product features or service benefits
• Strengthen your value proposition to better cater to prospects
• Improve customer retention rate
• Better understand buyer behavior
• Get ideas for future product development
• Gain a competitive advantage
• Identity service gaps

For example, let’s say your win-loss analysis shows that the reason a deal fell through was because the prospect didn’t understand the product and its use cases. It can inspire your marketing team to fix the messaging, marketing collaterals, or look into if that lead was the right one to begin with.

Summing up…

Understanding why you lost a deal is as crucial as understanding why you won. By analyzing your failures and successes, you can optimize your strategies to improve your close rate and conversion rate. 

Focus on the prospect's needs, build strong relationships, and leverage technology to streamline your sales pipeline. Remember, the key to deal closure lies in adding value at every stage and being seen as a trustworthy and reliable partner.

By addressing the learnings from your win/loss analysis, you not only improve your deal closure rate but also set your team up with a great sales routine for their long-term individual success too.