In sales, there’s no such thing as a stupid question – mostly
  • sales
  • Blog post

In sales, there’s no such thing as a stupid question – mostly

True or false: Salespeople should emphatically NOT ask their prospects stupid questions. True.

True or false: Salespeople SHOULD emphatically ask their prospects stupid questions. Also True.

Huh? How can both of these 180-degree-opposed statements be true?

Because there are stupid questions that you should ask, and then there are “stoopid” questions that you shouldn’t.

What’s a “stoopid” question? Usually, it’s one you should already know the answer to. The fact that you don’t reveals that you’re uninformed and/or haven’t done your homework.

‘Stoopid’ vs. stupid

Here’s how a question like that might sound:

Buyer: “So how can we integrate your solution into our CRM?”

Salesperson: “You use Salesforce dot com, right?”

Buyer: “I told you on our last call that we have a home-grown CRM.”

Oops. “Stoopid” question. It shows you weren’t paying attention or don’t care enough to take good notes.

OK, then. What’s a smart/stupid question sound like? Let’s return to the scenario above, where the buyer believes your software solution MUST be integrated into their CRM.

Buyer: “So how can we integrate your solution into our CRM?”

Salesperson: “Why do you need to integrate it?”

Now there’s a stupid question to prize. It sounds naive, maybe even childlike, to the buyer. But the question is carefully calculated to spark her curiosity. It encourages the buyer to review and explain the rationale behind her assumption, and possibly to reconsider it. Let’s call this kind of question a smart/stupid question.

Feels so good

There’s a reason people like being asked smart/stupid questions — because the way the human brain works, it feels satisfying to answer them.

Researchers in the Psychology Department at Harvard wondered what went on in people’s brains when they were asked certain kinds of questions – specifically, questions that challenge them to think; that is, to formulate opinions or judge the opinions of others. The researchers used brain scans on volunteers and the experiment showed that answering these questions caused the subjects’ brains to release the neurotransmitter dopamine and “light up” brain areas associated with reward and pleasure.

When you ask smart/stupid questions, you’re inviting buyers to do just that: formulate an opinion, and judge the opinion you’ve just hinted at. And it makes them feel good all over.

Here’s how the conversation might continue:

Salesperson: “Why do you need to integrate our software into your CRM?”

Buyer: “Because it must be integrated and here’s why … (the buyer explains five reasons)

At this point in the conversation, the buyer is feeling proud of herself, because she’s just delivered a cogent analysis of her position and her brain is flooded with dopamine. The salesperson’s smart/stupid question is what made that happen.

Challenging assumptions

But the buyer remains curious about why the salesperson asked the question.

Buyer: “You seem to be saying it’s not necessary. Is that right?”

Salesperson: “That’s what I’m saying. It’s not necessary.”

Buyer: “But I want integration anyway.”

Now it’s time for another smart/stupid question that will challenge the buyer to reconsider her assumptions about how the integration might affect the business.

Salesperson: “Help me understand how the benefit of integration outweighs the cost?”

On one level, that’s a stupid question because nobody would do something that costs more than it’s worth, right? But on another level, it’s a smart question because the buyer doesn’t know what the salesperson knows – that integrating this software product is easy with Salesforce but prohibitively expensive with homegrown CRM systems.

The buyer, who hasn’t adequately thought through the costs, will go through a process of discovery and learn that it makes no economic sense to integrate the software into his CRM. She will feel enlightened by the conversation and be inclined to work with a salesperson who challenges her brain with such good questions.

Make your own

In your industry, how can you come up with smart/stupid questions that are simple and almost naïve-sounding? It’s harder than you think. Here are some examples. Imagine asking these questions with child-like curiosity:

  • “Your building security system broke last year. Why haven’t you replaced it?”
  • “How do customers react when deliveries are late?”
  • “You said assembly line errors increased this year. How did that affect your production output?”
  • “What if you just stopped doing background checks on new hires?”
  • “The software you’re using is no longer supported. Why haven’t you updated it?”

Simple, stupid questions — that also happen to be smart.


This blog entry is adapted from the Rapid Learning module “Stupid questions: A smart selling strategy.” If you’re a Rapid Learning customer, you can watch the video here. If you’re not, but would like to see this video (or any of our other programs), request a demo and we’ll get you access.

The blog post and Rapid Learning video module are based on the following research study: Tamir, D. & Mitchell, J. (2012) Disclosing information about the self is intrinsically rewarding. Proceedings of the National Academy of Sciences, 109(21), 8038-8043.

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