What's in a Question????

Growing up with English as my second language, I had to ask a lot of questions just to survive middle school. After only a year in the U.S., curiosity wasn’t optional—it was my lifeline to understanding my classes, my friends, and my new world.

What I didn’t realize back then was that this habit—the constant questioning and intensely listening so I could understand what the heck was going on—was actually training me for sales. What sometimes annoyed my teachers turned out to be one of the most valuable skills a seller can have.

Asking questions is powerful, but not all questions are created equal. Simply reading off a script or asking just to check a box doesn’t build trust or move deals forward. Great questions open conversations, uncover insights, and spark real dialogue.

In this newsletter, we’re diving into the real impact of questions in sales, with a three-part series:

1. The Power of Asking Questions in Sales – Not just why questions matter, but how top sellers use them to uncover hidden opportunities, shift conversations, and differentiate themselves.
2. The Power of Asking Why Not? – A personal look at how this bold question shaped my own career—and how it can help you challenge assumptions, spark creativity, and drive innovation. I’ll also share my TEDx talk on this exact topic.
3. What You Do After You Ask Matters Most – Because asking the question is just the beginning. We’ll explore how the best sellers listen, respond, and add value to turn questions into real influence.

The Power of Asking Questions in Sales

In sales, the questions you ask aren’t just tools for gathering data/info—they’re keys to uncovering insights that drive deals forward. Research from the Journal of Personality and Social Psychology shows that people who ask more follow-up questions are seen as more likable. In sales, that likability can translate into trust—something that's essential in sales.

But the real power of questions goes deeper. Good questions open up conversations your competitors aren’t having. They uncover the “why behind the why”—the real priorities, challenges, and goals driving decisions. This insight lets you connect your solution to what actually matters to the buyer.

The best sales questions do three things:

1. Invite storytelling. Instead of “Are you facing challenges?”, ask, “As I was preparing for this call, I noticed on LinkedIn Insights that in the last year, you’ve grown your salesforce by 30%. How are you onboarding thing? I'm curious, what has been the ramp-up time? And how are you reducing that?”
2. Show you’ve done your homework. Skip surface-level questions you could Google. Use what you know to ask smarter, deeper questions.
3. Demonstrate curiosity. Follow-ups like “Tell me more…” or “What led to that decision?” show you’re actively listening—not just waiting for your turn to pitch.

The goal is dialogue, not an interrogation. A well-placed question can unlock an entirely new opportunity. In your next sales call, ask yourself: are you gathering data, or are you discovering what really makes your buyer tick?

The Power of Asking Why Not?

In sales, we’re taught to ask smart, open-ended questions to uncover needs, build trust, and move deals forward. But there’s one question most sellers overlook—the simple but powerful Why not?

Asking Why not? pushes beyond surface-level discovery. It challenges assumptions—yours and your customer’s—and opens the door to possibilities no one considered. 'Why not explore a different approach? Why not accelerate that timeline? Why not reimagine how you solve this problem altogether?'

This mindset isn’t just helpful in sales conversations—it’s essential for innovation, problem-solving, and personal growth. When you ask Why not?, you invite creativity, challenge the status quo, and often uncover hidden opportunities others miss.

In my TEDx talk, The Power of Asking Why Not, I share how this simple question shaped my own career—and how it can do the same for you. Whether you’re a sales professional trying to break into a new account or a leader navigating change, embracing Why not? can shift your perspective and lead to breakthroughs you never saw coming.

?? Watch the TEDx Talk: The Power of Asking Why Not

As you prepare for your next sales call, think about this: what bold, unexpected question could you ask to open a new door? And if something seems out of reach, just pause and ask yourself—why not?

What You Do After You Ask the Question Matters Most

Asking great questions is step one. But what happens next—the way you listen, respond, and add value in the conversation—is what separates average sellers from trusted advisors.

Too often, salespeople ask questions just to collect data. The buyer talks, and the seller is already thinking about their pitch. This “listen to respond” approach misses the point. Great sellers listen to understand. They focus fully on the customer’s answer—not just the words, but the meaning behind them.

When you listen to understand, you naturally uncover follow-up opportunities like:

• “That’s interesting—what led to that shift in priority?”
• “You mentioned X was a challenge. How have you tried to solve that so far? What has been the impact”

This turns the conversation into a real dialogue—not an interrogation. But understanding alone isn’t enough. You need to add value in the conversation itself. That could mean sharing relevant insights, offering a fresh perspective, or connecting the dots between their challenge and a creative solution they hadn’t considered.

When your questions lead to valuable moments of discovery (instead of just extracting information), your customer feels heard—and they see you as a resource--a trusted advisor--not a vendor.

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