Unveiling a Decade of Win-Loss Insights

Introduction

Welcome, everyone. I’m Ron Carson, and today we’re going to dive into the blind spots that are costing you millions. We’ll be unveiling a decade of win-loss insights, sharing some eye-opening discoveries while protecting the identities of those involved.

About Me

I’m a career marketing professional who’s also carried a sales quota. Over my 25-30 year career, I’ve run marketing departments in both Silicon Valley and the Research Triangle Park area in North Carolina. Through these experiences, I’ve adopted a “just ask” philosophy. It sounds obvious, but if you want to know how to market and sell something to someone, all you have to do is ask.

This approach has evolved into what we now call Third Side, a company I founded years ago. The rationale behind the name is simple: there are three sides to every story – your side, their side, and the truth, which is the third side. We position ourselves as partners in problem-solving for our clients.

Today’s Agenda

1. Why you need win-loss analysis
2. Introduction to blind spots
3. Common issues in win-loss scenarios
4. Uncommon but illustrative examples
5. What’s the fix? (WTF)
6. Do’s and don’ts
7. Additional resources

Why You Need Win-Loss Analysis

The loss reasons in your CRM are typically vague or not actionable. Sales reps aren’t paid to look in the rearview mirror and assess what they could have done better. We’re paying them to look ahead and chase the next revenue opportunity. No matter how many dropdowns we add to our CRM, they’re never really sufficient.

Studies vary, but our internal research over a decade confirms that a large portion of your win-loss data in your CRM is wrong. It’s been as low as 50-60% and as high as 70-80%, but it’s reasonable to assume that about 75% of your win-loss data is incorrect. That’s alarming, especially when you’re making decisions about win rates and loss reasons based on such flawed data.

Introducing Blind Spots

Every company has blind spots – things happening in your sales process and go-to-market motions that you don’t even know exist and are costing you revenue. These blind spots can extend all the way back to marketing:

• Bad messaging brings poorly qualified prospects into the top of the funnel
• Sales might not be doing enough discovery, failing to align with customer needs
• Generic demos that don’t address specific customer problems
• Products that don’t actually differentiate in the ways that matter to customers
• Bundling strategies that don’t match what customers want

The point is, you’re losing deals for reasons you don’t even know exist.

Common Blind Spots

Price Isn’t Always What You Think

When you lose a deal due to “price,” it’s not always about being too expensive. Sometimes it’s about:

• Targeting the wrong size account (e.g., selling a 50-user solution to a 2-user company)
• Pricing model complexity (customers can’t predict costs beyond year one)
• Deep discounts that backfire (raising suspicions about your product’s value)

“Lost to Competition” is a Cop-Out

Saying you lost to competition isn’t enough information. There are underlying reasons being missed:

• Was it really about price?
• Were there missing product features?
• Did sales make mistakes?
• Did the competition do a better job of discovery and aligning to customer needs?

Messaging Matters

Vague messaging leads to bad leads. Generic buzzwords like “strategic optimization” might bring in curious looky-loos, but they often don’t convert. Other messaging issues include:

• The right value proposition isn’t always what you expect (sometimes it’s about employee satisfaction or retention, not just ROI)
• Undifferentiated messaging makes you disposable (if all vendors sound the same, customers don’t care who they choose)

Not Understanding Customer Needs

This is a huge issue we see in almost every win-loss project. Up to 60% of losses can be attributed to not understanding customer needs, often manifesting as generic demos that don’t align with the problems customers are trying to solve.

The No-Decision Dilemma

No-decisions are often perceived as long maybes, but they typically break down into three categories:

1. No opportunities (e.g., trade show business cards, courtesy demos)
2. Actual losses where you weren’t part of the final decision
3. Potential win-backs (customers who might re-engage if approached correctly)

Uncommon But Illustrative Examples

Following Instructions Off a Revenue Cliff

A client, an approved vendor in their market segment, was instructed to wait for RFPs and not contact business units directly. Meanwhile, their competitors maintained relationships with business stakeholders, positioning themselves as consultative advisors and even architecting sole-source requirements that bypassed the RFP process entirely.

Overwhelming the Customer: Optics Matter

In a market where the buying process involved RFPs, shortlists, and pitch days, one client consistently made it to pitch day. Their strategy was to showcase their comprehensive solution by bringing multiple experts to address any possible question. However, what they intended to demonstrate as depth and breadth of expertise, customers perceived as bloat, bureaucracy, lack of accountability, and potential cost overruns.

The AI Implementation Hurdle

An AI company selling to the martech stack did an excellent job describing what their solution does and why it’s needed. However, they kept losing deals because they never explained to prospective customers how to implement this solution into an already complex technology stack.

What’s the Fix? (WTF)

If you’re doing win-loss analysis on your own, here are some do’s and don’ts:

Do:

• Conduct win-loss analysis (it’s hugely valuable)
• Use interviews rather than surveys
• Ask probing questions
• Cover a wide range of topics
• Set aside enough time for the entire process

Don’t:

• Rely on surveys
• Try to revive a sale
• Try to explain or be defensive
• Be apologetic

Additional Resources

We’ve made some practical tips available for doing win-loss analysis in-house. You can find an ebook with more information, including considerations for who should conduct the interviews, at thirdside.com/pavilion.

Remember, there are trade-offs to having different teams (marketing, product, sales) conduct these interviews. Consider these factors carefully when setting up your win-loss analysis process.

Download Our Complimentary Win-Loss Analysis Guide:

“Expert Tips for Conducting Your Own Win-Loss Analysis”

While Thirdside offers professional win-loss analysis services, we understand that some companies may choose to conduct their win-loss research in-house. This comprehensive guide provides practical strategies for effective win-loss analysis, covering:

• Dos and don’ts of win-loss interviews
• Key areas to explore in your win-loss research
• Choosing the right win-loss analysis interviewer
• Identifying and addressing blind spots in your win-loss process