The Right Sales Questions Will Get the Right Answers


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What happens when we make assumptions?

The movie, The Return of the Pink Panther, provides a great lesson. Peter Sellers, playing the immortal Inspector Clouseau, sees a small dog in a hotel lobby, and asks the clerk, “Does your dog bite?”

The clerk responds “no,” and Clouseau reaches to pet the dog, which immediately bites his hand.

“I thought you said your dog did not bite!” he exclaims. To which, the clerk replies, “That is not my dog.”

In sales, how do we know if our prospective customers are answering the questions we think we’re asking? How do we know if we’re asking the best questions—or even the right questions? The Pink Panther vignette illustrates both humorously and poignantly what can happen if we take actions when there are incongruities between questions and perceived answers. I can relate to Clouseau’s not-entirely-self-induced folly, and I wondered whether sales questions I’ve used could be similarly entertaining fodder—or, at the very least, instructive. So I reflected on my inventory of sales calls over 20 years and came up with two examples—one showing failure, the other success—that illustrate what can happen when you’re asking questions in selling. My conclusion: Getting to the right answers requires careful thought and constant practice. There aren’t any shortcuts, but there are some best practices.

A failure

I worked for several weeks to secure an appointment with the vice president of operations for a large national chain of dollar retail stores, which I’ll call Stuff for a Buck. My company’s product was a suite of bar code scanning hardware, software, label printers and services. To prepare, I studied the dollar chain’s distribution, logistics and competitive challenges. I was ready for The Meeting at Stuff for a Buck.

After asking mostly ordinary empirical questions such as: “How many trucks? How many warehouses? How many shipments per day? And how many stores by region?” I moved to the pain part. (I was told early in my career that a big part of selling is to “find out what keeps the customer up at night.”)

“What goes wrong in your daily operations?” I asked. The VP responded, “It’s quite common to put the wrong load on the trailer. For example, the truck going to Charlotte might actually be carrying the inventory that’s supposed to go to Wilmington. It happens quite often throughout our distribution network. We haven’t found a way to prevent it.”

Ka-ching! I hit what-keeps-me-up-at-night pay dirt! My supposedly keen industry insight caused me to extend his answer into the downstream logistics migraines that Stuff for a Buck must experience: heavy trailer loads of goods shipped in error all over the country. Goods in transit out of control and arriving in unintended locations. Stock outages. Customer service issues. After collecting some more data from the VP and offering him the hope that my proposal would eliminate his problems, we exchanged pleasantries about kids and golf, and I departed his office.

Using what he’d told me, I developed a proposal for a real-time, multi-warehouse inventory control system, including 200 handheld and mobile terminals and dozens of radio frequency access points. Inventory movement would be efficiently and accurately recorded with the simple pull of a scanner trigger. No more mistakes. No more manual data entry. No more paper. All this for $300,000—an excellent value considering the multimillion-dollar scale of the company’s inventory and transportation costs. Of course, I forecast my sales opportunity to close in the current fiscal year and received kudos from my district and region managers for having uncovered such a valuable lead. High fives were given all around, and we believed we couldn’t lose. I sent the sales proposal to my prospect and awaited the affirmative response, which never arrived.

Why? The major reason was because I hadn’t explored or understood the problem’s impact on the enterprise. As the VP later explained, “We sell everything for a dollar. Our customers don’t expect to see specific items in stock, so it’s not a headache if the wrong truckload backs up to the store’s receiving dock. They’ll unload it and put it out for sale. We don’t like it, but it doesn’t really matter to us in terms of our financial performance.” End of story. My opportunity was lost. My prospect eventually became someone’s customer. But not mine.

What did I learn? First, that the VP had answered my question as he heard it. I had asked, “What goes wrong?” when I thought I was asking, “What goes wrong that matters to you?” I misconstrued the gravity of the problem because it was the first one the VP mentioned.

Second, my industry knowledge had mutated into myopia, which prevented me from asking the right follow-on questions. Had I been a little more curious, I would have asked questions that would have helped me gain more insight, such as: “What is the consequence when the wrong goods show up in Charlotte? What does this problem cost per occurrence and annually? What impact do those costs have on overall financial objectives? How will this problem affect strategic goals if unabated?

Third, by tackling the first problem the VP described, I failed to complete the picture. I didn’t ask, “What else?” followed by questions that would have not only exposed problems far more consequential to the organization but also provided me with a broader perspective on its operational issues.

Finally, my discovery process should not have been limited to talking with just one individual. I should have taken the time to ask networking questions, by which I could expand my contacts and gain a breadth of opinions and information—like a wiki model in which the value of the answer increases with multiple viewpoints.

A success

At a different company, I sold Oracle integration services to firms in the mid-Atlantic area. Our short-term objective was to sell services for installing the next version of Oracle’s operating system, but my company’s California-based staff and lack of local references made that challenging. Yet our consulting practice leaders were resolute on promoting such high-dollar, long-term projects. Consequently, my initial prospect-qualification questions centered on whether the prospect planned to upgrade to Oracle 11i in the next 12 months. Most didn’t. After a few weeks of cold calling, I finally obtained an appointment with the IT manager of a distributor I’ll call XYZ Healthcare Products, though he was reluctant to talk about upgrading.

When I arrived at XYZ, I learned that the IT manager had invited eight colleagues from other departments to join our meeting. We began our discussion about whether there was a business case to upgrade to 11i. The more questions I asked about upgrading, the clearer it became that it wasn’t necessary. The conversation began to trail off as people looked at their cell phones and watches. Was it time to end the meeting and check my Blackberry for the Next Opportunity on the way to my car?

I didn’t because something piqued my curiosity: Why were there were eight people assembled to discuss something that appeared all but decided? Although I didn’t ask that question, I decided to ask a different one: “Assuming that technology and finances posed no constraints, what would you change right now about your business processes and operations?” The IT manager shared that a significant unsolved problem was that the company needed to produce a customer-ready invoice that could be placed in the shipment box during final packing, and Oracle’s “vanilla” software couldn’t provide that capability, causing XYZ to delay invoicing. His response surprised me because superficially the problem seemed minor, but his comment elicited nods from his colleagues.

That answer meant that the massive consulting project I needed to close had just devolved into a few billable hours to provide this seemingly-prosaic modification. Considering how insistent my practice managers were about selling upgrade work, I could have lost my sales resolve. Instead, I wanted to know more. What was it about this issue that created such visceral pain among these managers? As my mind filled with questions, I asked, “What does this limitation mean for your operations?” Their answers exposed issues ranging from customer service to logistics to receivables administration.

Probing the receivables challenges yielded insight into perhaps the greatest strategic challenge XYZ faced. The invoicing delay caused significant cash-flow problems. “Why haven’t you fixed this already?” I asked. “We thought it couldn’t be done, and, up to now, no one has taken the time to come here to meet with us.” I explained that providing the change they requested was not complicated. XYZ’s president was then called to join the meeting, and he excitedly corroborated what his managers had told me. The company signed a contract for the modification and became a client.

What did I learn? First, my central qualification question, “Do you plan to upgrade to 11i in the next 12 months?” was based only on what I wanted to sell; it risked missing opportunities because it ignored uncovering the outcomes my prospects required. By asking the right questions, I was able to learn that the immediate burning issue could be located in an unexpected place, and by providing a solution to address that issue, I could create a new sales path toward my higher-dollar work: the 11i upgrade service package.

Second, by removing constraints from the possible answers, I was able to eliminate boundaries that prospective customers often impose on themselves. Similar to vendors, prospective clients develop myopia based on perceived technical, financial or resource limits. Gathering requirements information that is unbound by those limits is important early in the sales process because discovering what the prospective customer wants is more valuable than discovering what he thinks he can get. Both questions must be asked, however, because the answers matter—and are often different.

How can salespeople improve discovery skills? Here are the key habits for success:

  • Bring an insatiable curiosity to your appointments.
  • Don’t assume you know the answers to your most important questions.
  • Endeavor to see the world through your client’s eyes. This empathetic view requires one to ask questions.
  • Listen for unexpected answers, probe further and have the agility to capitalize on the resulting opportunities.

The president of a large local real estate company recently told me that he views asking questions as the single most important selling skill—and that few agents do it. Extrapolate that problem to other industries, and it’s no wonder that many companies suffer from low sales productivity.

In August, I performed a nationwide survey of sales professionals about how they use questions to discover customer needs. The answers revealed a wide range of patterns, techniques and favorite questions, suggesting that there are many pathways to successful discovery. The best idea I received was this one: “If I’m unclear about who, what, when, where and why, I keep asking questions.”


  1. I am brand new to consulting and business development and can tell from my brief experience that the best practices mentioned in this article is spot on! One book that I continually use as a resource is “Let’s Get Real or Let’s Not Play” by Mahan Khalsa that discusses many of the best practices extensively in his book.

    Recently, I attended a sales meeting with a large logistics company in the southeast and was surprised that 4 additional heads of marketing were in the meeting. The meeting started off very awkward as I was attempting to get the prospect to start talking about their problem and they were waiting for me to “kill them by power point.” Because I was sufficiently prepared for the meeting (nor expecting 4 other heads of marketing to attend) I don’t remember what was said in the meeting or how we can help them.

    While I consider the meeting “a failure – defined as unable to market our consulting services to them” it was a great business development experience that taught me not only to be prepared from a company’s perspective, but to have a curiousity about my prospect in such a way to ask questions to truly uncover the real opportunities – not the ones that I think exist.

    Great article Andrew!

  2. Regarding Art’s comment: I read “Let’s Get Real or Let’s Not Play,” several years ago, and often re-read sections. It contains excellent sales questions and presents how to create a foundation of trust, which enables discovery in the first place. Like Art, I highly recommend the book.

  3. There are no stupid questions, but salespeople should be able to ask questions customers are interested to answer.

    Whatever questions asked, always ask questions with an objective in mind.

    Daryl Choy, the founder of Touchpoint eXperience Management, helps firms make a difference at every touchpoint. Choy can be reached at

  4. Thanks, Daryl. Good points. Your comments highlight a gap between the books and articles about asking questions and practice. Questions can seem perfunctory and ingenuine if the verbal inflections are wrong or if the questions are asked because of an obvious lack of preparation.

    “Can you tell me about your business?” could be a rapport breaker or rapport builder, depending on how the person asking the question presents it.

    The written words don’t communicate the genuine curiosity and empathy that must be present in any meaningful dialog. When both are brought to meetings, conversations will be genuine and productive as well.


  5. Andrew
    Keen observations- agree completely. How many times have we made assumptions and offered a solution because that is what we do well or offer, even though the client has no needs for it?
    I always mention when I am presenting ideas that ‘these ideas are based on my assumptions (if they are) and I need to hear from you whether they are in line with your needs/concerns.”
    This way you get alignment and build a level of respect with the client.


    Trip Allen, Team Egyii, Singapore

  6. It was nice to see the failures with the successes and this is a good lesson for all salespeople to learn. I had a previous Manager who always told me how the company used to be and put a negative twist on, what I thought to be, an exciting appointment. When I learned not to listen to what went on 3-4 years ago, I was able to identify new opportunities and be more successful.

    Thanks Andy!

  7. Dear Andrew,
    thank you for your very vivid explanations with that I fully agree. I think if we manage to take a “systemic approach” in a way that we really want to understand the “customer system” (either the company or the person in front of us) and how it works and thinks, it is very important to ask the right questions that make the customer think.

    One kind of these questions I am explaining in my blog:…ales-questions/

    As a result we will receive answers that really matter.

    I look forward to further exchanging ideas with you.

    Best regards, Christoph

  8. Very enlightening stories on failure and success in the IT Sales world! Note how in both cases Andrew didn’t just demo and go for the close, but asked questions…and got different results because of *where he left his curiosity*.

    Notice also, in the Oracle story, how he was initially interested in whether they wanted to upgrade or not. *Nobody*–no high-level decision maker–just wants to upgrade! Take that as a lesson, all you IT VARs: “upgrade” = “unnecessary cost” to business people. And business people are who are at the top of the food chain. Finding out instead what is “keeping them awake at night” is great advice.

    Great questioning skills are indeed the most frequently missing skills for salespeople. Merely demoing your solution and hoping they’ll buy because of the features and benefits that you list is not enough.


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