I lost a £6,000 deal by giving a perfect answer to the wrong question. Has this happened to you?
A prospect asked me what our uptime SLA was.
I gave a perfect answer. 99.97%, monitored independently, full transparency dashboard, historical data going back 18 months.
They said they'd think about it and went dark.
Three months later I found out they'd chosen a competitor. When I asked why, the real issue was something completely different. They needed to know we could handle a specific edge case in their data pipeline. They never asked that directly. I never thought to ask what they were actually worried about.
I answered the question I was given, not the question behind the question.
£6,000 deal. Gone. Not because of our product. Because I listened to the words and not the worry.
Has this happened to you? A deal lost not because you got the answer wrong but because you were answering the wrong question entirely?
What did you learn from it?
This is a painful lesson. I think the hardest part is realizing that the prospect's question is often just a proxy for a risk they're trying to understand. Asking “what makes that important to you?” might reveal more than giving the perfect answer.
That's the exact diagnostic question I should have used. "What makes that important to you?" forces them to surface the underlying risk instead of letting you guess. The mistake I made was taking the question at face value rather than treating it as an invitation to find out what was actually behind it. The feature question was never about the feature.