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Day39 | Challengers Sell More

Updated over 3 months ago

Part One: The Challenger Sale

One Key Insight

The Challenger Sale study analyzed over 6,000 salespeople across 90 industries and found that the most successful reps don’t just build relationships—they challenge their customers. In fact, 53% of customer loyalty is driven by the sales experience, not just brand, price, or product.

The Challenger Sales Rep

Challenger reps don’t just respond to customer needs—they shape them. They educate, guide, and control the conversation as experts.

The Six Traits of a Challenger:

  • Offers a unique perspective

  • Engages in strong two-way communication

  • Understands the customer’s value drivers

  • Identifies the customer’s key economic drivers

  • Is comfortable discussing money

  • Applies pressure when necessary

The Three T’s of the Challenger Approach

  • Teaches – Provides valuable insights that change the customer’s thinking.

  • Tailors – Customizes the sales pitch to align with decision-makers’ priorities.

  • Takes Control – Leads discussions, especially around pricing and objections.

Why Challenge?

Challengers don’t just sell—they provoke thought, challenge assumptions, and drive action.

  • They confidently call out excuses versus real objections.

  • They have crucial conversations that move deals forward.

  • They avoid the “friend zone” of sales, where deals stall and never close.


Part Two: How to Challenge

One Key Insight

Building relationships matters—but not in the way we’ve been taught. The best salespeople blend relationship-building with a Challenger mindset.

The Data Behind the Challenger Approach

  • 40% of high-performing reps primarily use a Challenger approach.

  • Top performers are twice as likely to be Challengers.

  • More than 50% of all top sales reps fit the Challenger profile.

  • Only 7% of top performers rely purely on relationship-building—the lowest-performing approach.

Challenger One-Liners (Touchpoint #7)

  • "Has anyone else worked as hard as we have to earn your business? Then what’s stopping us from getting started?"

  • "Remember when we first talked and I said, ‘[Insert belief statement],’ and you agreed? So what’s really stopping us now?"

Challenger Sales Techniques

  1. Power Frame – Own the conversation.

    • Let them feel in control, but remain the expert.

    • If they challenge you, stand your ground.

  2. Analyst Frame – Speak their language with data.

    • Bombard analytical buyers with proven statistics and ROI-driven insights.

  3. Time Frame – Create urgency.

    • "We’ll be deciding next week, and we’re meeting with three others."


Part Three: Challenge to Overcome

One Key Insight

Once you’ve built trust, you can challenge prospects directly: "What’s really stopping you from getting started?" By the seventh touchpoint, real objections surface—and you cut out the fluff.

Two Types of Responses: Excuse vs. Objection

  • Excuse – A hesitation with no real weight. Call it out.

  • Objection – A valid concern (budget, timing, decision-maker). Overcome it.

Industry-Wide Common Objections & How to Overcome Them

  1. Money – Shift the conversation to investment-based language.

    • "You get what you pay for. Would you rather invest upfront or lose money later?"

  2. Timing – Create urgency.

    • "Waiting costs you. Every day we don’t act, you lose 10% momentum. In six months, you’ll be in the same spot."

  3. Competition – Acknowledge but differentiate.

    • "I respect them. But here’s why clients choose us: [insert unique value]."

  4. Decision-Makers – Identify the real power player.

    • "Your wife prefers the other provider? Let’s make sure she’s fully confident in our solution."

  5. Already Using Someone Else – Position yourself as the second opinion.

    • "That’s great—let’s compare. Worst case? You validate your current choice. Best case? You find a better fit."

Your Turn: List Your Top 5 Common Objections : What objections do you face most? How will you challenge them?

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