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Every once in a while, someone asks me, “When is it right to challenge?” At first the question bothered me, my knee jerk reaction was, “We should be challenging our customers 100% of the time.”

Then I realized may have been answering a question that is different than what the person is asking.

Even though Challenger was published years ago, there remains a lot of misunderstanding around the concept Challenging. Many tend to think of it as a behavioral style–perhaps slightly aggressive, perhaps confrontive. When you look Challenger up in the dictionary, there are phrases, “someone who disputes something, or places themselves in opposition to something.” Others refer to “engaging in a contest,” with its implicit win/lose, or connotations of someone doing something right or wrong.

Based on those interpretations of Challenge, it’s easy to see we may want to be very careful about Challenging, even whether we want to do it at all.

But, I’ve always tended to think of Challenging in a different context. I’ve always viewed it in the context of getting people to think differently, getting them to imagine new possibilities. (I don’t think that’s inconsistent with the way Matt, Brent, and Nick have thought, either). It is less a behavioral style and more a set of conversations engaging the customer in learning new things and considering alternatives. It needn’t be bold insights, it could be simple questions, “Have you ever considered…..,” “What if…..”

As a result of that mindset, I tend to think our job as sales people is to always be challenging.

Selling has always been about change. Whether it’s changing the way you are doing a certain thing, changing from a current vendor or solution, getting the customer to think or alternative solutions to their problem.

People tend to be blind to, or resist change. They may not recognize there are better ways, they may not realize they are missing opportunities. They may just be too busy, surviving the day to day. As a result, we have to challenge them, we have get them to consider changing, we have get them to realize the pain/risk of not changing is far greater than the change itself.

Many may be down their buying journey, self educating themselves on their digital journey. They may not be asking themselves the right questions or looking at the right issues. They may be constrained by their past experience. If we are to get them to change, we have to challenge their thinking, we have to get them to consider alternative approaches.

To me, challenging our customers is an inherent part of every sales effort.

If our customers don’t need this challenge, if they have challenged themselves, determined a course of action and are taking it, then all we become is order takers. Order taking is not selling.