January 2, 2025

Insight

Stop Marking Your Own Homework

“I’m sick of our sales reps marking their own homework.”

That’s what a frustrated GM of Sales told me recently when I asked him why they had finally decided to bring in a third party to conduct their Win/Loss Reviews.

Up until now, their process for evaluating losses was simple: after every deal was lost, the sales rep would log into the CRM, select a loss reason from a drop-down menu, and write a few notes. That was it. Unsurprisingly, the reasons for losing deals often boiled down to the same three culprits:

  1. Price – The product was too expensive.

  2. Functionality – The solution didn’t meet a critical need.

  3. Do-Nothing – The client stuck with the incumbent or made no decision.

At first glance, these reasons might seem reasonable. But if this sounds familiar, it should raise some red flags. Why? Because this approach is fundamentally flawed.

The Problem with Self-Assessments

The challenge for this business—and countless others I’ve worked with—is that there’s no scrutiny applied to the reasons being provided by the sales team. Let’s break it down:

  • No Validation: The sales reps’ opinions aren’t being corroborated by decision-makers on the customer side.

  • No Data: There’s no quantitative or qualitative data to analyze what really influenced the outcome.

  • No Lessons Learned: Without genuine insights, the cost of sale is written off with nothing to show for it.

As a result, these companies are flying blind. They’re left relying on vague feedback and informed guesses to understand why deals are lost—or even why they’re won. This lack of visibility is costing businesses far more than just revenue; it’s preventing them from learning, adapting, and improving.

The Current State of Play in B2B Sales

For many quota-carrying sellers reading this, let me be clear: this isn’t me calling you out. This scenario is the norm in most B2B companies. Here’s how it usually plays out:

  • Sales teams chase down every opportunity, respond to tenders, send proposals, and conduct countless discovery calls and demos.

  • They follow up, circle back, and touch base—doing everything they can to keep the deal alive.

  • Finally, they wait, hope, and pray for the decision to come in.

When the decision filters back, they’re often left with a vacuum of information about what really influenced the outcome. Feedback is typically limited, vague, and non-descript:

  • "You were too expensive."

  • "We went with another solution that better met our needs."

  • "We decided not to move forward right now."

With this scant information, reps fill in the blanks as best they can, make some educated guesses, shrug their shoulders, and move on to the next deal.

The Hidden Cost of Marking Your Own Homework

Here’s the harsh truth: the way most companies handle post-deal analysis is wasting their cost of sale. Every discovery call, demo, and proposal represents an investment. When you fail to extract meaningful insights from the deals you lose—or even the ones you win—that investment yields no return.

The trust and professional courtesy you build during the sales cycle is a form of currency. If you’re not using that currency to ask customers for honest feedback at the end of their buying process, you’re leaving immense value on the table.

Why Third-Party Win/Loss Analysis Changes the Game

There’s a better way to approach this. Companies that stop marking their own homework and turn to third-party Win/Loss Analysis gain access to insights they simply can’t uncover on their own. Here’s why:

  1. Unbiased Feedback: Customers are far more likely to share candid, unvarnished feedback with an impartial third party than they are with the sales team that pitched them.

  2. Holistic Data Collection: Third parties like Trinity collect both quantitative and qualitative insights, uncovering the emotional and rational drivers behind buying decisions.

  3. Actionable Insights: Third-party analysis digs deeper than surface-level explanations like “price” or “functionality.” It reveals what really influenced the customer’s decision—whether it was trust in the salesperson, perceived risk, or competitor positioning.

While it’s possible to conduct Win/Loss Reviews internally, the reality is that you’ll never achieve the same level of depth or objectivity. This is why many companies invest in external agencies to elevate their understanding and take their sales processes to the next level.

The Payoff: Real Lessons from Every Deal

When you treat Win-Loss Analysis as more than a checkbox exercise, you create a continuous feedback loop that helps your team grow and improve. Here’s what this looks like in practice:

  • Losses become lessons, helping you refine your discovery process or better address objections.

  • Wins become scalable, as you uncover what worked and how to replicate it.

  • Assumptions are replaced with clarity, allowing you to focus on what truly matters to your customers.

By leveraging third-party insights, you’re not just reacting to feedback—you’re building a foundation for long-term success.

Final Thoughts: Stop Guessing, Start Learning

As an industry, we need to stop marking our own homework. If we genuinely want to improve sales outcomes, we need to treat the post-deal process with the same professionalism and rigor as the sales cycle itself.

Your cost of sale should earn you the right to extract value—irrespective of the sales outcome. By partnering with a third-party Win/Loss Analysis provider, you can gain the insights you need to stop guessing and start learning.

It’s time to stop settling for vague feedback and start uncovering the real drivers behind your wins and losses. Your sales team—and your bottom line—deserve better.

Ready to stop marking your own homework? Partner with Trinity or another trusted Win-Loss Analysis agency to gain the unfiltered insights that drive results. Let’s talk.

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