Just the Facts? Sales Discovery Requires More than Asking “Killer Questions”


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Every day, salespeople receive gobs of well-intentioned advice, including:

“Shut up and listen!”
“Being interested is more important than being interesting.
“Telling is not selling.”
“The Right Sales Questions Will Get the Right Answers.”

If only things were that easy. Simply asking questions and listening won’t solve our most vexing sales challenges. Probing questions followed by patient listening as the magic keys to sales success. But here’s a plain fact that many people ignore: Conversations carry questions. And sales questions minus conversation equals interrogation. I know. When it comes to conversational rapport, some sales meetings go better than others.

Yet, hard-sell hype about the power of questions drives many people to website altars in search of A Better Way. Do you really believe in

“Killer sales questions?”

“Sales questions that close every deal?”

“The 12 best sales questions to ask?”

We count on the promise of such “hot ideas” and shortcuts to help us become more productive. No doubt, for many people, this is all very confusing. Should we ask open-ended questions? Closed-ended questions? “Facilitative” questions? Who cares! If salespeople can’t embed sales questions into meaningful, rapport-laden dialog, the best sales questions in the world take sales opportunities down a path to nowhere.

Salespeople—it’s time to talk! Questions need the medium of conversations in order to work. It’s what we do! But this time, let’s call it dialog! As our top-producing salesperson, Denise, said in an earlier CustomerThink article, To an Octopus, ’50’ Means Nothing: Why Empathy Matters, “. . . I think about what I’m going to ask and say.” In that order. Denise doesn’t dismiss the importance of her contribution to the conversation.

From her desk in the depths of the call center cube farm, Denise has a key insight. With all the attention we heap on asking good questions, do we honestly believe prospects will spontaneously open up? Is “ask a Really Good Question, get an answer,” a simple, straight line? Or, is there more to it than that? How do we create what author Jim Collins described as an environment where the truth is heard?

Here are a few ideas:

Make your intentions and motivations clear from the outset. As Mahan Khalsa wrote in Let’s Get Real or Let’s Not Play,“you will communicate your intent whether you want to or not . . . Based on your intent, people will decide to trust you or not.”

Share your expertise throughout the discussion. No one likes a know-it-all, but as a prospect, would you rather share your answers with an expert or a greenhorn? As Jill Konrath, author of Selling to Big Companies, said, “the best sales questions have your expertise in them.”

Demonstrate that you are connecting the dots. Sharing your insights throughout the conversation not only makes it clear that you’re listening, but also helps to ensure understanding.

Be transparent, not opaque. It’s hard to ask for a prospect’s candor without being similarly forthcoming about your enthusiasm and concerns. Being open with both enables reciprocal dialog.

Above all, don’t be afraid to talk. Sales discovery works best in a conversation.


  1. Hi Andy

    Insightful post. I cant tell you how many times I’ve witnessed the mechanical interrogation of a customer which, unless they are really patient or really desperate, usually resulted in failure.

    Who wants to be “sold to?” By contrast, my favorite sales partner approached each customer engagement almost like a date. He was great at setting the tone with light humor and mildly personal anecdotes and then matching the cadence of the customer toward those deeper questions we needed answers to. In short, he took time to get connected with them intimately before broaching any serious subject.

    I believe doing this takes a good sense of emotional awareness and social grace that eludes us many times. Perhaps sales training should be more around understanding how to read people’s emotional states and understand how to connect and engage them rather than canned power questions and manipulation tactics.

    Thanks again for making us think!

    Don F Perkins


  2. Don–your comments are much appreciated. I realize from your remarks that I left out an important point: to break tension, judicious use of humor works wonders.

    Your last paragraph reminds us that good conversational practices should appear natural; they don’t need to be explained or rationalized. If you’re trying to “get the prospect to open up and share their pain,” maybe you’re trying too hard.

  3. Andrew, I agree with the premise of your title (“Just the Facts? Sales Discovery Requires More than Asking ‘Killer Questions'”), and the material in your post that supports that thesis.

    But your post seems to veer to a different topic in that you appear to be debating with other bloggers and authors and implying they are suggesting that ONLY questions will get you sales. Where I disagree with you is that I don’t think the sources you link to or any sales guru is suggesting that “only question” drive sales.

    You write: “But simply asking questions and listening won’t solve our most vexing sales challenges. If only it were that easy.”

    None of the fellow sales trainers or experts I trust would ever say that (1) selling is easy; or (2) simply asking questions will solve vexing sales challenges. That would be like implying that you are saying “only conversation” drives sales.

    The reality is that conversation is important, empathy is important, questions are important, and a bunch of other stuff is important, too, in successful selling.

    Don’t you agree?

    You write: “Should we ask open-ended questions? Closed-ended questions? “Facilitative” questions? Who cares!”

    I care. And anybody selling should too. Because different types of questions give a different type of result. That’s like saying “who cares if your surgeon uses ACME anesthesia in the operating room or if they use XYZ Corp anesthesia? Who cares!”

    I care 🙂


  4. Skip: thanks for taking the time to share your thoughts. I agree that as salespeople, experience enables us to put our own context around the sales tips that rapidly scroll across inboxes and on websites.

    But not every salesperson is experienced. What is misleading are the absolute terms that pepper our discourse. In this case, “killer,” “every,” and “best.” (For me, “Killer,” conjures the image of the Wicked Witch of the West skywriting “Surrender Prospect!” in place of “Surrender Dorothy”)

    As you said, “a bunch of other stuff is important, too.” Questions are but one tool used in the process of discovery. Isolating questions from situation and context is comparable to writing an article for surgeons entitled Best Instruments for Tonsillectomies. As a medical practitioner, could you improve your patient outcomes without any information about surgical techniques or patient condition? Are we promoting realistic expectations when we do the same with lists of great questions?

    With sales questions, false expectations and confusion are byproducts most familiar to me. After twenty years of selling, I haven’t found “questions that close every deal.” (Even “Can I have the order?” doesn’t work if other right stuff doesn’t surround the question, or if the timing is poor.)

    Sweating over open-ended questions vs. closed ended questions, as some articles and blogs do, creates needless anxiety if a salesperson really doesn’t know what he or she is after in the first place. I can’t think of a sales engagement I’ve worked on where both haven’t been important.

    There are great sales questions. There are bad, weak, good, and better questions, too. But they can’t be mastered out of context. For salespeople that means asking “What answers must be gained for a successful sales outcome? How will you know when you know? What processes, resources, environment and interpersonal dynamics (trust, empathy, etc.) are required to uncover the truth? What questions should be asked? How should they be asked?” These are not philosophical questions. The answers underpin every sales conversation.

    Most salespeople will be better served by understanding these than by looking for silver “question bullets.” When you know what you need to know, and the process for getting to the answers, the questions very often take care of themselves.


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