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#31Chapter 05 — The Objection Handling Masterclass: Turn "No" Into "Tell Me More"
I need to practice objection handling before a high-stakes call. Play the role of a prospect and make me work for it.

**My context:** I sell [what you sell] to [buyer type]. My company is [brief description].

**The prospect you're playing:** [Role, company type, size, industry. Personality: skeptical / analytical / impatient / hostile — pick one or describe]. Background: [Any relevant details — they've been burned before, they're evaluating competitors, their CEO is risk-averse, they're under budget pressure].

**Difficulty level:** [1 = cooperative, 2 = skeptical, 3 = hostile]

**Rules for you as the prospect:**
- Stay in character throughout. Don't break to offer advice mid-conversation.
- At Level 2+: don't accept my first response to any objection. Push back at least once.
- At Level 3: you've talked to our competitor and liked what you saw. You know our product's weakness is [name it]. Challenge any vague claim with "Can you be more specific?" or "Prove it."
- Raise objections naturally — don't list them. Weave them into the conversation the way a real buyer would.
- If my response is weak, show it through your behavior (skepticism, going quiet, changing the subject). Don't explain why it was weak — make me feel it.

We'll go 7 rounds of back-and-forth. After round 7, break character and give me:
1. A score out of 10 for each of my responses, with one sentence explaining why
2. The moment I was strongest — what I did right and why it worked
3. The moment I lost you — what I said that made you pull back
4. A rewritten version of my weakest response
5. One thing I should practice before the real call
Claude for Sales
Claude for Sales

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