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

Updated to Business, Habits on December 14, 2022.

I was in a car the other day with a radiologist and a neurosurgeon talking about hypertension. 

This conversation is actually not as unusual as it might sound. I volunteer for a local society that does trail clearing in a popular hiking and mountain bike park and many of the volunteers happen to be recently retired doctors. 

Back in the car, one of the doctors happened to mention that recently his medical partner, who is in his early 60’s, had a mild stroke. As we wound our way further up the dirt road to our work site my education continued. 

I learned that strokes are the second biggest cause of mortality worldwide and the third most common cause of disability. The scary statistics get worse. As you age your chance of a stroke doubles every 10 years after 55

There’s a checklist of health conditions that make you more susceptible to a stroke, like obesity, high cholesterol, and diabetes. But the biggest culprit – six times out of ten – is hypertension or high blood pressure. In my books, that’s worth paying attention to.

What’s interesting is that stress, in itself, is not the direct cause of high blood pressure. It’s what we do when under stress that leads to nasty results. We eat too much, drink too much, and move too little. Basically, we deal with stress by making unhealthy choices.

For me, stress starts with worry.

Ngoc Son Temple, Hoan Kiem Lake, Hanoi, Vietnam

I’ve had a lot of worries

There is a world of problems you can worry about – take your pick. You can worry that Ukraine will be pummeled into a tiny province of rubble, or that we’ve passed the tipping point with global warming, or the tiny spot on your chin is cancer. 

Or not.

“I’ve had a lot of worries,” quipped Mark Twain “most of which never happened.” Our mind loves a good worry. Like a dog chewing a bone, we want to turn our worry around, looking from all angles, poking and prodding until it swells up into something bigger than it really is.

I used to worry incessantly before every keynote speech. I’d worry I’d miss my flight or wasn’t prepared enough, or I would be greeted by the “audience from hell.” Trust me, when you have 60 minutes to educate, entertain, inspire, motivate, and get laughs from an audience you’ve never met before, any sane person would invent a long list of worries.

It was at one of those events when a fellow speaker opened an exit door for my worries. He suggested that audiences don’t want you to fail – in fact, they want you to succeed. “They want to see you having fun—enjoying yourself. That way,” he explained, “they can enjoy the ride with you.”

When I accepted the long list of what I could never control – my flights, the audience, the speaker before me going overtime – I was free to focus on what I could control.

Enjoying the moment. 

What your life will have been

In her book, Comfortable with Uncertainty, Buddhist nun Pema Chödrön tells the story of delighting in the preciousness of every single moment.

A woman is running from lions. She runs and she runs, and the lions are getting closer. She comes to the edge of a cliff. She sees a vine there, so she climbs down and holds onto it. Then she looks down and sees that there are lions below her as well. At the same time, she notices a little mouse gnawing away at the vine to which she is clinging. She also sees a beautiful little bunch of strawberries emerging from a nearby clump of grass. She looks up, she looks down, and she looks a the mouse. Then she picks a strawberry, pops it in her mouth, and enjoys it thoroughly.

Learning what to focus on, and what to ignore, seems to be the ultimate secret to living a healthy, stress-free life. “Whatever compelled your attention from moment to moment,” writes Oliver Burkeman in Four Thousand Weeks (a must-read for anyone over 50), “is simply what your life will have been.”

So, what are you focussing on?

What to focus on

You can learn a lot when you’re the dumbest one in a car full of doctors. I learned that strokes are a silent pandemic. And that hypertension is the leading cause of that pandemic. And I learned the leading cause of hypertension is stress. 

I was also reminded that stress is a choice.

We all have lions and tigers in our life. Maybe even a mouse or two gnawing away at something we value. Meanwhile, we have the moment.

Choosing what to focus on (and what not to) might just be the healthiest choice you can make.

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Photo of eggs by Nik on Unsplash
Photo of Ngoc Son Temple by author
Photo of tigers by author

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.


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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.

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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.)