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🔍Discovery & QuestioningIntermediate· 4 min read

Asking better sales questions

Yes/no questions get nothing. Calibrated questions get the truth.

Combine fundamentals with timing and read.

The principle. A great question feels easy to answer and surfaces information the buyer didn't know they had. Closed questions ("Do you have a budget?") get monosyllables. Calibrated questions ("How did you arrive at the budget you have in mind?") get stories.

Five high-leverage questions.

  1. "Walk me through how you're handling that today."
  2. "What would have to be true for this to make sense?"
  3. "If we did nothing, what does that cost you in 6 months?"
  4. "What's the hardest part of this for you personally?"
  5. "Who else is part of this decision, and what matters most to them?"

The follow-up rule. Every answer earns a "Tell me more about that…" — at least once. The second answer is always richer than the first.

Key takeaway. Better questions don't require more skill — they require fewer yes/no traps and more "how" and "what."

Mini drill

Pick 3 of the 5 questions. Use them on your next call. Note which got the longest answer.

Flashcards
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Practice out loud

Drill this lesson in Voice Gym

Say it out loud and get scored on confidence, tone, pacing, and delivery.

Drill out loud
Sources & further reading
  1. BookNeil RackhamSPIN Selling (1988)

    12-year, 35,000-call study behind Situation/Problem/Implication/Need-payoff.

    https://www.huthwaiteinternational.com/spin-selling-the-book
  2. BookDavid SandlerYou Can't Teach a Kid to Ride a Bike at a Seminar (The Sandler Selling System) (1995)

    Pain funnel, up-front contracts, Sandler reversal, no-guts-no-glory close.

    https://www.sandler.com/
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