There's a quote I come back to often when I'm working with leaders and sales teams:
"The smartest person in the room isn't the one talking the most—it's the one asking the best questions."
It's easy, especially in leadership roles, to feel like your job is to have the answers. You've got the experience, the title, the track record—so naturally, the instinct is to share your knowledge and tell people what they should be doing. After all, why wouldn't they want to benefit from your hard-earned wisdom?
But here's the thing: If we're doing all the talking, we're probably not doing enough leading.
The Problem with Talking Too Much
When we lead with advice, we might accidentally shut down the conversation we need to have. The more we talk, the more we risk filling the space where our team—or clients—should tell us what's going on. And if we're being honest, most people aren't that eager to interrupt the boss.
The result? You leave the meeting thinking you've been clear, supportive, and strategic… but they leave feeling unheard, frustrated, or even micromanaged.
Why Great Leaders Ask Better Questions
Good questions do more than gather information. They create buy-in. They build trust. They invite the other person to think, reflect, and engage. When you ask a great question, you're not just collecting data—you're empowering the other person to arrive at their own conclusions.
That's where the real magic happens. People support what they help create.
This is one reason I believe in the Sandler system and tools like the Pain Funnel and Negative Reverse Selling. These aren't just sales tactics—they're communication strategies that help people discover their motivations, obstacles, and solutions. And that's far more powerful than anything you could tell them.
Moving from Telling to Asking
Here's what this might look like in action:
- Instead of saying, "I need you to prospect more," ask,
- "How comfortable are you with the current prospecting plan? What's getting in the way?"
- Instead of, "We're not hitting our numbers because the pipeline isn't full," try,
- "What are you seeing in the market right now? Where do you think the gaps are?"
- Instead of assuming your client needs a bigger discount, ask,
- "Can you help me understand what's most important to you in making this decision?"
Notice the shift? These kinds of questions invite conversation. They create space for honesty and allow you to guide the dialogue, without taking control away from the other person.
Some Of My Favorite Questions
Here are a few of my personal favorites. These have served me well whether I'm coaching a sales team, leading a tough conversation, or working with a long-term client.
"When you’ve thought about what truly needs to change, what’s been going through your mind?"
This one comes in handy when I feel the urge to jump in with advice (something many of us struggle with). It gives the other person control over whether they want your input instead of forcing it on them.
"On a scale of 1 to 10, where are we on this issue? “Where 1 is we are good to go, and 10 is we need to start over.”
This question is great for leadership check-ins, team coaching, or even in a sales process when you need to understand someone's level of investment. It forces clarity and opens the door to the obstacles standing in the way.
"What happens if we do nothing?"
This one cuts through the noise. It's a powerful sales question, but it works just as well when you're leading internal projects. It helps people get honest about urgency—or the lack of it.
"Can you help me understand how you came to that conclusion?"
Notice it's not, "Why did you do that?" One triggers defensiveness, while the other invites a thoughtful discussion. I lean on this one when emotions are running high or when there's a decision I don't quite follow.
These questions share a common thread: they aren't about having the right answer but about making sure we're asking the right questions.
When you lean into these kinds of questions more often, you'll find people listen better, share more openly, and walk away from conversations feeling heard, respected, and clear on what happens next.
Great leadership isn't about having all the correct answers—it's about asking the right questions at the right time. When we talk less and ask more, we create conversations that lead to real solutions, not just surface-level compliance.
If your leadership conversations aren't producing the clarity, accountability, and action you want, it might not be about what you're saying. It might be about what you're asking.
Want to sharpen your team's questioning skills and communication strategies? Reach out to see how we can support stronger, more effective conversations for your organization.
