I spent nine long months pursuing what seemed like the perfect deal, only to walk away empty-handed.
It took me three months to seed the idea. Three more months to get them talking about it. And a final three months to realize this deal wasn’t going anywhere.
This experience early in my Microsoft career transformed how I approach deal qualification forever.
The opportunity seemed golden: a university had taken over management of 300+ engineering colleges across an entire state. With one agreement, we could transform education for 10,000 students simultaneously. I had personally connected with the Vice Chancellor and was certain this deal would close.
After all, I represented Microsoft – who wouldn’t be thrilled to partner with us?
Here’s where I went wrong
I was so full of myself, convinced I was doing everything right. I was measuring progress by my own actions – the meetings I scheduled, the presentations I delivered, the follow-ups I sent. But what truly matters isn’t what you do; it’s what your customer does in response.
The 20-20 Insight: Measure Customer Actions, Not Yours
This early loss taught me the most crucial lesson of my sales career:
it’s not about what I think – it’s all about what the customer thinks.
The real indicators of progress aren’t in your calendar or task list. They’re found in:
- Your customer’s concrete actions – Are they inviting additional stakeholders? Sharing internal information? Committing resources?
- Their genuine reactions – Do they engage meaningfully in discussions? Challenge assumptions constructively? Show enthusiasm about outcomes?
- Their honest perceptions – How do they view your solution? Do they see it as mission-critical or just nice-to-have?
This insight has guided my work with Fortune 500 clients ever since, helping their sales teams identify which deals will actually close – and which ones are consuming valuable resources with little chance of success.
When I began focusing on these signals instead of my own effort metrics, my close rates dramatically improved.
Deals that weren’t progressing became obvious much earlier, allowing me to reallocate my time to opportunities with genuine momentum.
As the saying goes, hindsight is 20-20. With this framework, you can develop the foresight to qualify deals effectively from the start.
I don’t want you to discover after months of hard work that your deal isn’t progressing. I want you to win more, which is why I’m passionate about sharing these deal qualification insights.
Remember: In sales, progress is measured by your customer’s actions, not your own.
Looking forward to helping you win more.
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