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Insight Selling: Challenger Sale or Fail?


Guest articles > Insight Selling: Challenger Sale or Fail?


by: Michael Harris


How do you deliver insight to your customers so that it challenges the status quo without challenging the customer?

Well, when you get sick, do you ever go onto WebMD before you visit the Doctor? So when you show up at the doctor’s office, all you want him to do is to write you a prescription for what you feel you need? And if the market for buying prescription medicine was truly a competitive, wouldn’t you also be looking for a better price?

Don’t you think customer’s do the same thing before they speak with a salesperson? If we accept the current research from The Challenger Sale, customers are 60% of the way through the buying cycle before they engage a salesperson. Because they’ve already done most of their research online, Customers may have already decided what they want to buy, so they may only be looking for salespeople to provide the best price.

Now if customers could go online and make a good buying decision, they wouldn’t need us. But Doctors and salespeople will tell you that they don’t. Imagine a doctor, for example, asking a patient, “what’s wrong?” And the patient says, “I was bitten by a mosquito, and with the West Nile virus in the area, I’m concerned. According to WebMD, I have the identical symptoms, and the recommended treatment is penicillin.” “I see,” says the doctor, “let me write you a prescription right away.” Of course this would never happen, because it’s the doctor’s job to challenge their patient’s self-diagnosis. Doctors have to re-teach what their patients have learned online so that their patients end up with the right treatment.

It’s the same with salespeople. With the proliferation of information and advice on the internet, customers are drowning in information. They don’t need more information. What they need is to know what the information means. They need insight. So the days of the walking brochure salesperson is dead. Today, salespeople need to be able to challenge the status quo by delivering insights that cause the customer to re-examine if the risk of the status quo is greater than the risk of change.

But how do you challenge the status quo, without challenging the customer, especially when you have salesperson written on your business card?

  1. You could challenge them directly, but that can often come across as an attack. This can end up in an argument that the salesperson will never win, because the customer is both judge and jury.
  2. You could ask questions, but questions work better at firming up an established belief. However, if you try to lead customers to insight with questions, it’s very difficult, because the customer does not have a frame of reference to reflect on something new. So the customer can’t connect the dots that lead to insight, because they’re in the dark. Thus, we all know that good salespeople ask questions, but they just don’t lead with questions when they deliver insights. Instead, they lead with third party research or a story, and they then follow-up with questions.
  3. You could use third party research. This is an excellent way to deliver insights, because it’s objective, so the customer doesn’t feel attacked. Unfortunately, third party research is scarce, so it’s seldom an option.
  4. Or you could wrap your insight in a story. Because a story is about someone else, the customer doesn’t feel attacked. A story simply presents a scenario that allows the customer to draw their own conclusions. Without feeling pressured, the customer can now relax and listen to your message, and possibly gain enough insight that they start to tell themselves a new story, where new choices make more sense. It’s as if a story enables your customers to step inside a buying simulator®, and take your product out for a virtual test drive.

But challenging the status quo requires more than just the skill to deliver insights, because it presupposes that you have insights to deliver. And what happens when these elusive insights aren’t available? It may then just come down to whoever tells the best story wins.


From Michael Harris: As CxO of, I enjoy showing salespeople how to position their unique capabilities in a way that will inspire their customers to buy through the power of storytelling.

With a graduate degree in Finance and 12-years on Wall Street, I have learned how to build business value. I then ran a finance company that grew to 125 employees and 250MM sales, and it was here I learned the power of loading the lips of your salespeople with the right messages. I then worked as a Business Partner at a Solution Selling Sales Training company and, after 5-years, I refined the totality of my many years of experience and formed Insight Demand.

Additional resources:

Interview with the author of The Challenger Sale: "How do you challenge the customer's thinking without challenging the customer?" (click here)

If you'd like me to speak at your sales conference, (click here) for speaking reel.

Contributor: Michael Harris

Published here on: 20-Oct-13

Classification: Sales



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