Negotiation often feels like magic or luck—but Never Lose Again shows that strong negotiating comes down to asking smart questions. The authors offer 50 specific, carefully crafted questions designed to help you gather information, build leverage, break deadlocks, and get better deals. Whether the negotiation is big or small, professional or personal, using the right questions at the right time gives you control, credibility, and confidence.
🔑 Key Concepts
🧠Stealth Information Gathering
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Ask innocuous questions early on to get your counterpart talking. These reveal motivations, timing, constraints, and needs.
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Example: “How did you hear about us?” helps uncover hidden angles and build rapport.
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Another: “What is your time frame for wrapping up this negotiation?” reveals pressure points and how urgent the other party is.
💪 Anchoring & Power Tools
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Use questions to establish or test leverage: “Do you have full authority to negotiate and finalize this deal?” ensures you’re speaking with a decision-maker.
Bring up alternatives: “What alternatives do you have?” pulls out backup plans and gives you context and fallback power.
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When possible, subtly show constrained options or urgency to shift leverage toward you.
🚀 Breaking Deadlocks & Creating Opportunity
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If things stall: “Are you willing to get creative here to find something that works for both of us?” helps shift conversation to problem-solving mode.
Questions like “Does my proposal work for you?” test fit and allow the other side to accept or propose adjustments.
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Closing time: use questions that ask for commitment while keeping respect—e.g. “Can we set up a time to finalize things?” or “Would you like to move forward now?”
💬 Handling Price & Value Discussions
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Ask about pricing flexibility: “How much flexibility do you have in the price?” opens space for negotiation.
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Use comparative questions: “What is the most you have ever paid for this type of product/service?” or “Are you aware of industry standards here?” to benchmark value.
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Also, test client priorities: “Are you more interested in quality or in price?” helps you align your offer with what really matters to them.
🛠️ Wrapping Up & Gaining Commitment
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As negotiations near conclusion, ask: “Does my proposal work for you?” to gauge acceptance or objections.
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Time boundaries: “Can we agree to put the past behind us and focus on the future?” refocuses on forward movement.
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Ensuring clarity: ask for confirmation or summary to avoid misunderstandings. Close with specific next steps.
✨ Final Thought
Never Lose Again teaches that negotiation isn’t about aggression or bluffing—it’s about curiosity, listening, strategy, and timing. By mastering questions that uncover information, test fit, and direct the flow of conversation, you gain not just better deals—but also stronger relationships and more confidence at the table.

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