The Deal That Taught Me I Was Asking the Wrong Questions

Kevin O'Neill
Jun 16
2 min read

Early on in my first job at Xerox, I was working a deal that should have closed. The buyer liked the product. The deal made sense. But every time I dropped in to follow up, the answer was the same:

“We’re not ready."

And the reason I kept getting.

"We have a top line sales target we need to hit first.”

I kept hearing that. So I kept asking when. When would they be ready? When might they revisit? Same polite brush-off every time.

“Once we hit a certain revenue number.”

Eventually I brought the deal to my manager. I walked him through the offering. The pricing, the follow-ups, everything. Told him the customer wasn’t moving forward until they grew their top line.

He asked me one question that stopped me cold:

“Do you know why that number matters to them?”

Aside from the obvious, I didn’t. So we went back to the customer together and asked a different set of questions.

Why that number? What changes when you hit it? What’s the real constraint right now? And that’s when the conversation changed.

It wasn’t about revenue at all. It was about profit. They weren’t chasing growth, they were protecting margin. Their costs were creeping up and they were watching every dollar.

That changed the entire pitch.

We reframed the proposal to show how our solution would reduce service and supply costs. Those savings would have the same bottom-line impact as increasing sales by six figures.

They finally made the purchase.

Not because we sweetened the deal or got better at selling, but because we stopped pushing and started listening.

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A few things that stuck with me:

- “Not yet” usually means “not like this”

- If a buyer gives you a number, ask what’s behind it

- You don’t need more pressure, you need more context

- Most deals aren’t won with pitch decks, they’re won in the questions