The Question That Makes Your Stomach Hurt Is What’s Standing Between You and the Sale

Every salesperson has been there. You’re in the middle of a conversation with a prospect, and a question bubbles up in your mind. It’s the tough one—the question that makes your stomach tighten and your pulse quicken.

You hesitate. You tell yourself, “I’ll ask it later,” or worse, you don’t ask at all. Why? Because it feels uncomfortable. What if the prospect says “no”? What if the question reveals objections you don’t feel ready to handle?

Here’s the truth: that uncomfortable question is often the key to closing the deal.

Why the Hard Questions Matter

Sales isn’t about surface-level conversations. It’s about uncovering real needs, addressing concerns, and creating solutions. The hard questions dig deeper. They force the prospect—and you—to face the realities of the deal.
For example:

• Budget: “Does this fit within your budget?”

• Timeline: “What happens if you don’t solve this problem in the next 30 days?”

• Decision-making: “Who else needs to be involved in this decision?”

These questions might feel risky, but they’re necessary. Without them, you’re operating in the dark, and that’s no way to close a sale.

Fear vs. Opportunity

When you avoid the tough questions, you might feel safe in the moment, but you’re setting yourself up for a potential loss later. On the other hand, asking those questions creates opportunities:

• Build Trust: Prospects respect honesty and directness. When you ask bold questions, you show you’re serious about solving their problem.

• Uncover Objections Early: It’s better to address concerns head-on than to lose a deal over something you didn’t know was an issue.

• Position Yourself as a Partner: Tough questions show you’re invested in their success, not just your sale.

How to Ask the Hard Questions

1. Prepare Yourself:

Rehearse the question ahead of time. Get comfortable with how you’ll phrase it.

2. Use Empathy:

Frame it as part of understanding their needs. For example, “I want to make sure this is the right solution for you. Can I ask a tough question?”

3. Pause and Listen:

After you ask, give the prospect space to respond. Their answer will provide valuable insights.

The Payoff

Every time you push past the fear and ask the question that makes your stomach hurt, you grow as a salesperson. You learn more about your prospects, refine your approach, and increase your chances of closing the deal.

So, the next time you feel that twinge of discomfort, lean into it. That moment of courage could be the turning point in making the sale. After all, the only way to move forward is to ask.

What’s the one question you’ve been avoiding? It might just be the one that seals the deal.