They push. You explain. They push harder. You defend. They win.
The best negotiators don't defend. They ask.
Last week we gave you identity-based goals for 2026. This week, we're giving you a tool to protect those goals when they meet resistance.
This scene opens Never Split the Difference: Chris Voss, former FBI lead international kidnapping negotiator, walked into Harvard to meet Robert Mnookin, Chair of the Harvard Program on Negotiation. Mnookin sprung a roleplay: "We've got your son, Voss. Give us one million dollars or he dies."
Voss didn't argue. He asked: "How am I supposed to do that?"
Mnookin pushed: "So you're okay with me killing your son?"
Voss stayed calm: "How do I know he's even alive? How can I get you any money if I don't even know he's alive?"
The Harvard professors grew frustrated. They gave up.
Seven words. No defense. Total control.
📚 Framework in Focus: Calibrated Questions
The technique follows a simple structure:
Start with "What" or "How" → Opens dialogue and gives the other side the illusion of control. They feel heard, not cornered.
Avoid "Why" → "Why" triggers defensiveness. It sounds like an accusation. "Why would you do that?" puts people on guard. "How does this work?" invites collaboration.
Never ask yes/no questions → Closed questions give you one-word answers and no insight. Open questions make them think, reveal constraints, and expose what they actually need.
"How Am I Supposed to Do That?" → Voss's signature question. It says no without saying no. It shifts the problem back to them. And it works 9 times out of 10.
Use questions to say no → Instead of refusing directly, ask: "What would you like me to deprioritize to make room for this?" The other side now owns the tradeoff.
Voss puts it simply: "A good 'How am I supposed to do that?' question forces the person to take a hard look at exactly what they're asking. They may not change their mind. That's not the point. The point is to get them to stop and think."
🚀 Powerful Prompt
Build your calibrated questions before any negotiation, difficult conversation, or situation where you need buy-in.
Role
You are a negotiation strategist specializing in Chris Voss's Calibrated Questions framework from Never Split the Difference, helping leaders navigate resistance, objections, and difficult conversations without triggering defensiveness.
Context
Help me prepare calibrated questions for this situation:
Situation: [Describe the negotiation, conversation, or conflict]
Desired outcome: [What you want to achieve]
Likely objections: [What pushback you expect]
Their constraints: [What limitations they face]
Relationship dynamic: [Boss, client, peer, vendor, etc.]
Critical Guardrails
Base all questions strictly on the Calibrated Questions framework. No generic advice.
Questions must start with "what" or "how." Never use "why."
Avoid yes/no questions entirely.
Match tone to the relationship dynamic provided.
Task
Create 3 "what" questions that shape their thinking toward your desired outcome
Create 3 "how" questions that reveal implementation challenges or invite collaboration
Create 2 questions for handling the specific objections I listed
Create 2 "saying no without saying no" questions, including Voss's signature: "How am I supposed to do that?"
Output Format
Opening/Shaping Questions
Implementation Questions
Objection-Handling Questions
"Saying No" Questions
For each question, include a brief note on when to deploy it and what response to listen for.
💻 Copy-paste into ChatGPT, Claude, or Gemini. Compare results to see which resonates most.
What would help you get more from AI this year?
🧭 Try This Week
Before your next difficult conversation, write down three calibrated questions starting with "what" or "how."
When pushback comes, resist the urge to explain.
Try Voss's signature question: "How am I supposed to do that?"
Or ask: "What would you need to see to feel comfortable with this?"
Notice how the dynamic shifts when they start solving your problem for you.
✨ Ask instead of tell. Resistance dissolves. They sell themselves on your solution.
↗︎ Think Better. Clarity Prompts
