The Lost Art of Asking Better Questions
A customer tells you, "Your product is too expensive." Most business development professionals do one of two things: defend the price, or offer a discount. Both responses assume they already know what "too expensive" means. Usually, they don't.
There's a third option: "Our product is too expensive?" said back, almost verbatim, with a slight lift at the end. The customer fills the silence—and what comes out is rarely about price. It's about budget cycles, a competitor's quote, an internal approval threshold, or a return they're not confident they'll see. The first two responses argue with a guess. The third finds out what's actually true.
That's the mechanic underneath the mindset. You already walked into the conversation with a hypothesis about what's going on. This is where you find out if you're right.
Three kinds of questions, one purpose
The purpose isn't to collect answers. It's to gather enough of the right information to know whether there's a real fit—before you propose anything.
Open questions get the customer talking: what, how, why, tell me about. One worth having ready: "What's the cost of waiting?" It surfaces urgency the customer hasn't said out loud yet.
Reflective questions send something the customer just said back to them, for clarification or expansion. Used well, they surface roughly twice the information a purely open-ended approach gets you—that's the whole reason the echo technique works. This is particularly effective when a customer stalls: hand their own words back to them, like "I understand you want to wait. You told me your people need these skills." Just repeating what they already said, with no pressure attached.
Closed questions come later, once you've got what you need. They're for agreement, confirmation, and moving to a next step—not for discovery.
Most business development professionals skip straight to closed questions because they feel more efficient. They aren't. They just feel faster.
Once you know which one it actually is—budget cycle, competitor quote, approval threshold—you're not negotiating the same problem anymore. Each gets answered completely differently. Arguing price against the wrong one just proves you weren't listening in the first place.
Where it actually breaks down
A good question asked well still gets wasted if nobody's listening to the answer. The training shorthand for it:
Stop. Give the customer your actual attention—not "let me finish this thought first."
Think. Use the pause to separate fact from feeling, not to plan your next sentence.
Listen. For understanding, not for your turn to reply.
The biggest barrier isn't distraction. It's evaluation—forming a judgment about what someone's saying before they've finished saying it. Once you're mentally drafting your response, you've stopped listening, even if you're still nodding.
What this changes
None of this shows up in a formal RFP process. A written proposal answers the questions a buyer knew to ask. A conversation built on real questions surfaces the ones they didn't know were relevant—the budget constraint nobody mentioned, the internal politics behind a "no," the actual reason last year's vendor got replaced. That's information a competitor working from the same RFP never gets.
The best questions change what you understand, not just what fills the silence.
Most teams have the instinct to talk. Fewer have the discipline to ask, and fewer still sit comfortably in the silence after. Listening isn't a soft skill—it's the one nobody's training program fully owns, which is exactly why it's the first thing to slip.
Tell us where it's costing you—in sales, in leadership, in negotiation—and we'll build the training around that issue, not a generic one. Click here to book a free consultation and ask about our Business Development Program.
Warm regards,
The Executive Team
Gary Waldron & Associates
Comments