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Excerpt from Heart and Sell: 10 Universal Truths Every Salesperson Needs to Know available on Amazon here.

We all know the path to a sale is lined with effective questions. Most salespeople have a series of great, thought-provoking questions for their prospects, but deliver them in an off-putting way. Buyers recoil when you go too deep, too fast. They resent it when you ask them to fill out a checklist of predetermined questions without taking a personal interest in each response. They feel manipulated when you fire back solutions before delving deeper into their feelings and problems.

Conversely, when you are genuinely curious and thoughtful—even ask surprising questions—your prospects will respect you and connect with you.

Since how you ask is just as important as what you ask, I’ve developed a list of 7 tips for asking questions that will engage your prospects and turnthem into active participants in your sales process.

#1 Move from the general to the specific. 
 I like to start my discovery with a very general question like:

“Tell me about yourself and your company” or “Tell me about you and your training programs.”

Pay attention to whether the customer answers your question or tells you something else entirely (Like, “We’re just looking,” or, “We’re not happy with the service we get from your company,” for example). Their response will clue you in to what’s foremost on their minds and in their hearts.

#2  Let the customer finish his/her train of thought. According to an NBC News article, it takes just 4 seconds of silence for a conversation to become awkward. Disruptions longer that that “elicit deep-seated, primal fears of social acceptance and belonging.” The result? Salespeople often can’t stand the awkwardness of the silence, so they rush to fill the void. To have a meaningful conversation, in which you get to know each other well, you must allow for pauses and perhaps a bit of patience. What you think is the end of their train of thought may just be a long, mindful pause. Such pauses often result in a deepening of connection and vulnerability; exactly what you need to close the sale.

#3 Compliment; don’t criticize. Don’t ever put your customers on the defensive by challenging or insulting their current solution. Misguided salespeople often kill sales with comments such as:

“The learning software you’re using isn’t open-source. Our proprietary software is much better.” Or
 “You camp every year? Yuck. You should consider upgrading your travel.

As a general rule, when you tell someone what’s wrong with a product choice or idea, they’ll defend it and tell you what’s right about it.

Last year, my family and I traveled to a fly-fishing lodge in Alaska. A guest said to Max, the owner, “You must have non-stop headaches, being responsible for this place.” Max moved into full-on defense mode: “I get paid for fishing and flying a float plane. I love it!”

Two days later, another guest said his dream was to own a fishing lodge. Max confessed, “It’s non- stop, fixing the heaters, training the guides, and installing new gas pumps!”
Compliment your customers’ choices, past and present. Chances are better they’ll reveal their true problems and buying motives.

#4 Stay with your customer. Don’t ever hand your customer a survey and leave them to answer questions on their own. Likewise, refrain from sending discovery questions online, if possible. Leaving your customers to answer questions on their own is a recipe for disaster. Every time I’m asked to fill out a survey at the doctor’s office, I give the shortest possible answers and skip what I can get away with. Your customers are no different.

#5 Ask questions that reveal one of the Big Four. Great sales questions are never random. You must know exactly why you’re asking each question in advance to prevent asking annoying or irrelevant questions. Flying on autopilot doesn’t cut it. Write out your questions to ensure that each question is intentional and yields one of what I call “the Big Four.” Every question you ask should either:

  1. Uncover a fact
  2. Expose a problem
  3. Reveal an emotional motivator, or
  4. Unearth an objection

Check your discovery questions. Make sure each question fits into one of these 
four categories.

#6 Dig deeper. Ask questions, listen to the answers, and use the answers to ask the next meaningful question. Prospects will generally answer the questions you ask them, no more and no less.

When you ask a question, dig deeper and ask follow-up questions to get the rest of the story. I love to illustrate this point in seminars with a clip from the movie The Return of the Pink Panther.

The scene begins with Inspector Clouseau checking into a German hotel. He sees a small dog sitting next to the hotelier, and as he reaches down to pet it, asks, “Does your dog bite?”

The hotelier answers, “No.” Clouseau proceeds to pat the small dog’s head until the dog snaps and ferociously bites him.

“I thought you said your dog didn’t bite!” Clouseau cries. The hotelier replies: “That is not my dog.”

Asking the right questions is good. Asking appropriate follow up questions is better! You actually create closer connections and decrease the likelihood of getting “bitten” at the back end.

#7 Confirm customer information (create a feedback loop). Salespeople often assume they’ve discovered accurate information, but they miss, or misinterpret, critical facts. It’s essential to create a feedback loop. Why? Although simple facts—like the spelling of a name—are easy to check and correct, it’s much trickier to listen and articulate back how your customer feels.

After you ask the customer questions, you might say, “Thank you for sharing this information with me. It will help me narrow down what I show you and save you valuable time.” Then, repeat back names, dates, trigger events, and personal information. Confirm the customer’s emotional needs, problems and objections. Finally, gain agreement by asking

“Is there anything I missed?
“Any critical information you’d like to add?”
“Does this sound about right to you?”

Ask the right questions, at the right time, in the right way and the answers you receive will set you up for long-term success. This kind of methodological questioning, first proposed by Socrates some 2,400 years ago in classical Athens, has helped people and organizations clarify intentions, expand their thinking, and help opposing parties reach agreement ever since.

Mastering questioning techniques will help you open more hearts and close more sales.


  • Bruce says:


  • Thanks for the info graphic.

  • Shari Levitin says:

    You’re very welcome Kate!

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  • Shari Levitin says:

    Thank you Tera – I appreciate you following my blogs and glad to help.

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  • Glen Johnson says:

    Great article. Couldn’t be write much better!

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