Win rates and self-deception

A CEO of a startup brings me in to help accelerate sales.

I ask about win rates.

He tells me they’re “good” (circa 30%).

He believes the answer is just more pipeline.

But then we dig deeper.  And the illusion starts to crack.

🔹 The average sales cycle is six months.
🔹 If accurate, of the pipeline generated in January—50% won’t close until July.
🔹 And some deals? Won’t close until the end of the year.

So is the win rate really 30%?  Or is it just self-deception?

The reality:

❌ Most win rates are overestimated because they don’t factor in the time it takes for deals to close.
❌ More pipeline and hope isn’t a strategy—it’s a way to dilute win rates even further.

Here’s how to calculate win rates properly:

✅ Look at the pipeline at the start of the quarter.
✅ Measure how much of it closes within that same quarter.

That’s the real win rate.

With this clarity, you can adjust your strategy in the right proportions:

📌 if this ratio is low, focus on better sales execution.

📌 If you're executing at a truly strong yield, then yes— turn on the top-of-funnel tap (without diluting quality).

But guessing isn’t a strategy. Clarity is.

But I'm intrigued... anticipating a wide variety of approaches.  How do you calculate win-rate?

Written by Jonathan Stern
ICF Certified Coach | Gallup CliftonStrengths Certified | Former MuleSoft ANZ Leader
I coach high-potential leaders and high-potential scale-ups.
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