The Three-Step Guide to Becoming a Challenger Salesperson

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Aja Frost
Aja Frost





Sydney is an account executive for a paper supply company. David, the owner of three restaurant chains, is looking for a menu-printing vendor.

“Most of the restaurant owners I work with say they struggle to sell the high-margin, ‘splurge’ items on their menus,” Sydney says. “Is that something you’re experiencing as well?”

David says yes.

“I’ve seen a few strategies,” Sydney replies. “Some of my clients use their servers to promote certain dishes or do nightly specials. Typically, this results in 5% higher sales.”

Sydney pauses.

“But the truly effective technique is redesigning your menu. We’ve found simply moving your ‘star’ dishes to the top left corner of your menu increases order frequency by 25%. Using high-quality paper increases sales by another 15%.”

David is intrigued and impressed. He chooses Sydney’s company over two other suppliers who offer similar products at lower prices.

According to The Challenger Sale, 40% of high-performing salespeople use Sydney’s approach: The Challenger style. These reps set themselves apart by educating their prospects and disrupting how they think about their business.

Want to apply this style to your sales strategy? Here’s a three-step guide to becoming a Challenger salesperson.

How to Become a Challenger Salesperson

Step One: Identify Your Opportunity

The Challenger approach requires uncovering a surprising insight that helps your prospect improve their business -- and ultimately points them toward your product.

Sydney could have given David advice on improving customer experience. Yet unless she tied it to increased profits or decreased costs, he probably wouldn’t have felt a greater urgency to buy paper. Your teachable moment should ultimately make the buyer think, “I really need [your product].” If you’re not sure whether it does, ask yourself, “What’s the business value of following my advice? Have I made those benefits clear to my prospect?”

To find your opportunity to advise prospects, review the last 10 or so deals you worked. How are prospects routinely mismanaging their relevant business processes? What opportunities are they missing?

Here are some possibilities to get you thinking:

  • Inefficient process
  • Misallocated funding/budget
  • Lack of investment in one area
  • Product/pricing mistakes
  • Risky initiative
  • Wrong priorities
  • Poor staffing choices
  • Suboptimal team structure

Stumped? Try brainstorming with the other reps on your team. Spotting common themes is easier when you’ve got multiple people in a room.

You can also ask your manager for insights. Since she has access to several or all salespeople’s pipelines, she’s well-versed in recurring prospect challenges.

Note whether prospects are usually aware of this problem. If they’ve identified it but haven’t found a good solution -- or have underestimated the issue’s significance -- they’ve probably done some research. To help them, you’ll need to fill in their missing knowledge gaps and reshape their existing perspective.

But if most prospects have never thought about this specific challenge or opportunity before, bring it to their attention.

Step Two: Identify the Strongest Solutions

Pointing out an issue or opportunity won’t move the deal forward unless you also help the buyer address it. The next step is preparing a few strategies or recommendations.

Ask yourself how previous customers have reacted to this challenge. What has worked? What hasn’t?

If you’re having a hard time coming up with ideas, do research online. Imagine you want to help prospects raise their customer engagement rates. You might search “raise customer engagement rates strategy,” “customer engagement case study,” “techniques improve customer engagement,” and so on. Looking through your CRM and reviewing closed-won deals can also be helpful. Pay attention to common challenges and the ways prospects reacted. Were any of those strategies successful for multiple buyers? If so, it’s probably a technique worth recommending -- and as a bonus, you have evidence of its efficacy ready to share with the buyer.

Finally, you can reach out to current customers. Call five prospects you worked with in the past year and ask, “When we spoke in [month], you were focused on [solving challenge]. Which techniques did you try?”

Follow up with: “Which strategy was most successful? Which was least successful?”

Although gathering these responses takes time, citing real examples will earn you instant credibility with future prospects.

Step Three: Incorporate Your “Lesson” Into Your Messaging

Now it’s time to update your messaging.

At this point, you should have:

  • A surprising, valuable insight for your prospects
  • Two or three ways they can capitalize on that insight

Mentioning this insight in prospecting emails is a great way to grab your prospects’ attention and lay the foundation for a productive conversation. But make sure you don’t give everything away in your first message: You want to give prospects an incentive to talk to you. Try describing the impact of your suggestion rather than the suggestion itself.

Here’s an email Sydney might have sent David:

David, are you having menu profitability challenges?

Hi David,

Congratulations on opening a new restaurant in the South End. Judging by the early reviews, I need to go. Can’t wait to try the pasta that Globe reviewer called “life-changing.”

Many of the high-end restaurateurs I’ve worked with experience menu profitability challenges. I have an idea that could boost specific dish sales by 25% or more. Are you free on Thursday at 9 a.m. to discuss this idea?


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Once you’re actually speaking with the buyer, follow this template for introducing your insight:

Rep: “I’ve seen [challenge] come up again and again with my customers. Is that something you’re struggling with as well?”

Prospect: “Yes.”

Rep: “Have you thought about [X strategy]?”

Alternatively, you can:

  • Offer an unexpected fact: “Did you know [surprising thing]?”
  • Point to an issue they’re not addressing: “I’m curious, is there a reason you haven’t [solved X problem]?”
  • Identify a missed opportunity: “Given [benefits A, B, and C], have you considered [investing in initiative]?”

These statements help you challenge your prospect’s perspective without implying they’re unintelligent or inexperienced. After you’ve made them curious to hear more, offer your tips.

For instance, you might say, “My team has found doing X leads to [results], while doing Y leads to [results]. We believe the most effective approach is Z. Customers who try Z see [results].”

Once you’ve added significant value to the buyer’s life and helped them see their world in a new light, you’ll have earned their trust and loyalty. Many prospects struggle to tell the difference between products -- using the Challenger approach can be your competitive advantage.

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