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How to be a Challenger Seller

Three great ways to up your game


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I’m a fan of The Challenger Sale – despite the fact that the book came out the same year as mine (2011) and promptly soared past me.  If you’re not familiar with the book or the premise, authors Matt Dixon and Brent Adamson identified five types of sellers:  The Relationship-Builder, The Hard Worker, The Lone Wolf, The Reactive Problem Solver and, of course, The Challenger.

I’m not giving anything away when I tell you that they believe Challengers to be uniquely poised for success in today’s marketplace. Why?  Because Challengers enter each business opportunity with a deep understanding of their client’s business, tailor messaging to each role and are not afraid to question, yes, even challenge a customer’s beliefs.  All of which makes sense especially when many of us work with customers who are reluctant to move past the status quo. 

So can we all be Challengers?  What if you’re not part of that 27 percent identified by the authors as naturally predisposed to rock the boat?  What if you have spent years working at building relationships, solving problems or just plain, working hard?  Now you’re suddenly going to take a giant leap out of your comfort zone and confidently stride in with insights and challenge your client to see things differently?  Maybe, but the authors readily admit that moving a rep from one of the less desirable four types to a Challenger is “a tough barrier to overcome.” 

I’ve worked with sellers who have come out of Challenger Sale Training with all the tactics and tools only to get frustrated and fall off the path once they try to apply them.  Here’s part of the reason I believe that is:

Imagine an actor who has trained all his life to play Macbeth and suddenly he’s cast in, say, The Lion King.  Yes, they’re both kings, but that’s where the similarities end.  But unlike salespeople, actors have a methodology for taking on a new role that might be quite unlike themselves and making it their own so that they can confidently deliver it.  I’ve found this same methodology can be extremely helpful for salespeople struggling to take on a more assertive role like that of the Challenger.

Here are three ways you can become more of a Challenger with your customers:

Determine what challenging means for you

If your idea of challenging someone is fraught with tension and acrimony, you’re not likely to approach it with much enthusiasm.  If, on the other hand, challenging means offering up a fresh perspective, expanding someone’s horizons or helping them avoid a business disaster, it will become a whole lot easier to embrace and get behind.  So your first step may be to reframe your conception of challenging.

 Identify where you’ve been a “Challenger”

We all possess at least a grain of most human qualities within us.  Perhaps we simply haven’t used them recently or only think to use them in a very specific role.  Like an unexercised muscle, they’ve become weak and forgotten.  You can attempt to locate your “Inner Challenger” by asking yourself questions, like:  Where in my life have I challenged someone’s point-of-view in an effective way?  Perhaps you were discussing politics with a neighbor.  Making a case for why you shouldn’t receive a ticket.  Questioning your child’s choice of college that seemed to be based on the sole criteria of “best party school.”  Whatever it is, you may be surprised to find you have in fact, been effective at getting others to see a different p.o.v. in many areas of your life.  Now, how do you put that to work with customers?

Act as if

While only three words, this step is where the rubber meets the road.  To “act as if” you need to consider what actions you took when you had been a challenger in other roles and what actions you need to take now.  For example, you would seem to need confidence in order to deliver insights that are to be taken seriously.  What actions can you take to build confidence?  Honing your presentation and messaging skills might be a start.  In order to question someone’s beliefs it would call for showing respect and sensitivity.  What tools can you use to approach someone with sensitivity and respect?  How about stories, facts or studies that can be used to gently reframe and soften someone’s stance?

Embracing a more assertive role like The Challenger may not feel comfortable at first.  In fact, don’t expect it to.  But as a mentor of mine once told me:  “Don’t expect it to be so easy and it won’t be so hard.”  Start by challenging yourself to take one action each day that is a step outside of your comfort zone. 

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Julie Hansen

Julie Hansen, author of Sales Presentations for Dummies, helps sales and business executives craft and deliver winning presentations and demos by applying today’s best practices from business, acting, improv, and storytelling. Julie’s techniques for leveraging proven performance skills in presentations have been adopted by Fortune 500 companies across the globe, including IBM and Oracle, as well as local Colorado companies. Learn more about sales workshops and keynotes at  PerformanceSalesandTraining.com, start a sales conversation at Julie@actingforsales.com  or connect with Julie on LinkedIn.

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