The irresistible power of questions to get you more sales, love, and respect

Updated to Business, Habits on December 14, 2022.

When I was a kid we were told to shut up and listen. “Children are to be seen,” my dear Father would admonish “not heard.” So I didn’t speak up.

Later in life, I somehow gleaned the power of the spoken word. I discovered I could give instructions and motivate staff, sell clients, and extinguish the odd relationship fires. Progress.

But, I still hadn’t cottoned onto the most powerful piece of the communication formula: asking a good question.

In this post I’m sharing three reasons why questions will always get you more of what you want. Plus one very ingenious type of question you must master. But, before I get to that, let’s look at what happens when you do all the talking (yeah, I’m talking about you).


I was at a dinner recently where one person repeatedly turned the conversation to him. You could be talking about a trip you enjoyed – the next moment he’s talking about some distant cousin that once lost his luggage. 

Mention a client issue – he had one bigger. And on it went. Pretty soon people gave up sharing. He won—sort of.

There are three ways you lose when you do all the talking:

  1. you appear insecure, narcissistic, and oblivious. Let’s face it, it takes a secure person to not speak up – even when they can. Being a good listener is sign of strength.
  2. you lose control. The brain can process language at least four times faster than the mouth. So when you do all the talking, everyone else (like your client prospect) can think circles around you—like why they don’t want to buy from you.
  3. you learn zip. All relationships are richer the more you know about the other person. This is true in our office, sales, service, families, and with your local barista. If talking is telling, then listening is learning.

The opposite is also true…


There are, of course, two types of questions. Good ones, and stupid ones. Just kidding. A close-ended question leads to a Yes, No type reply and a short conversation. This is great when ordering an triple venti, soy, no foam latte – not great in negotiations.

Judge a man by his questions rather than his answers. – Volaire

An open-ended question leads to a sentence in reply. Much better. More potential.


IMAGES_key 7


Here are three reasons why these are better than talking at the person more:

  • you appeal to the person. Intelligent questions tell the other person you heard them, you’re interested, and you want to know more. Who wouldn’t like that?
  • you can direct the conversation. Imagine your client has three reasons why they aren’t ready to buy and one is because of timing. If you ask for more information about timing, guess who’s in charge now? And here’s funny thing: they won’t notice you didn’t ask about all their excuses.
  • you learn about them. On calls about my speaking my goal is to wait as long as possible before I tell them about my speech. I want to learn as much as possible and for them to know I want to learn. What I have to say is secondary to what I need to learn.

But, wait—I want to share a brilliant type of question you will definitely want to start using (hat tip to Matt MacEachern). It’s call the Double Click.


You can think of any high-stakes conversation (conflict, sales, feedback) like a funnel (see also my post “Five essential steps for resolving conflict and taming tigers”). At the top is a bunch of stuff you wan to say and even more from them. There often isn’t much organization – just lots of history, confusion, judgments, and demands. It’s a mess.

IMAGES_key 6

At the bottom of the funnel is agreement—that’s the goal. The Double Click is a question about what the other person said (the name comes from “double clicking” a link on the Internet to learn more. Hat tip to Matt MacEachern.) Your Double Click question is made up of: what you just heard, followed by a request to learn more. It could sound like this: “You are telling me you were pretty busy – tell me more about why you were so busy.”

I never learn anything talking. I only learn things when I ask questions. – Lou Holtz

It’s a classic coaching strategy: drill down on only the part of what they said that you think has the most potential, and ignore the rest. And it works like a damn.

You are appealing to the other person’s ego, you direct where the conversation goes, and you learn more about their needs. The perfect trifecta.


There is no other communication tool more under-utilized and more irresistible than the lonely question. Here’s why:

  • If I screwed up (no surprise there) and my wife, Kirsten is mad at me, I can’t talk my way out of it—it sounds like excuses. But, questions open a whole new door in the conversation that can lead to resolution.
  • If my employee screwed up, I do have to tell them why I’m not happy. But, after that I’ll start to sound like their parents and it won’t be productive. Questions help them come up with a way to avoid the mistake next time.
  • If my prospect is hesitating, ramming more information down the phone line won’t move them closer to a sale. I need to turn the tables and have them admit they need what I’m selling.  I can only do that with questions, Double Clicking on their reply, and moving them down the funnel.


For the next week, practice turning a question into a question. It sounds like this:

“No, I haven’t been here before. Tell me what you do.”

“I’m in sales in the medical services industry. Tell me, are you self-employed as well?”

Here’s another example:

“…after all that we decided to change hotels. Have you ever had a similar disaster?”

And, one example close to home:

“I feel like I’ve tried everything. Help me out, what ideas do you have?”

Try it out. You might be surprised how much better asking can be (even when you’ve got lots to say.)