Asking your customer this question will change everything

Simon Sinek once observed: “100% of employees are people. 100% of customers are people.”

It sounds obvious. But in practice, most customer conversations treat customers as accounts, not people. As problems to be managed, not humans with motivations, fears, and goals.

That gap — between treating customers as accounts versus people — is where most customer relationships break down.

A story from a banking client

Early in my career as a software account manager, I took over a banking industry client. Their competitor’s contract was about to expire. On paper, this was a straightforward renewal situation.

But instead of jumping to a product demo or a pricing conversation, I asked them one question:

“What does success look like for you — not for this contract, but for you personally, in your role?”

The conversation that followed was completely different from any sales conversation I’d been trained to have. They told me about the pressure they were under internally. About what they needed to show their leadership team. About what failure would mean for them personally.

That information didn’t just help me close the deal. It helped me understand what the customer actually needed — and serve them better for years after.

Why this question works

When you ask customers about their personal definition of success, you:

• Understand the human stakes behind the business decision
• Uncover information that no product demo or feature list can address
• Build trust by showing genuine interest in their outcomes, not just your contract
• Learn what “good” looks like to them — which is what you actually need to deliver

The question to ask

You don’t need an elaborate framework. You just need to ask, in whatever form feels natural to you:

“What does success look like for you?”

And then listen. Really listen — not to formulate your response, but to understand.

The answers will change how you sell, how you onboard, and how you retain customers. Because you’ll finally know what they’re actually trying to achieve.