How to Ask Better Questions and Negotiate More Effectively

The following insights come from the great Chris Voss.

Use them strategically to live a richer life.

Bad questions kill deals. They shut down conversations, create resistance, and destroy trust.

The Traps to Avoid

1/ Closed-Ended Questions

One-word answers stop the flow.

“Can we move forward?” → “No.”

2/ Yes-Oriented Questions 

Pushing for agreement creates resistance, not momentum.

“Do you agree this is a good idea?” forces compliance, not commitment.

3/ “Why” Questions 

Trigger defensiveness, making the other side feel judged.

The Winning Approach: Tactical Questions

Great questions shape the negotiation. They make your counterpart think, engage, and reveal what truly matters.

1/ Strategic “What” & “How” Questions 

Guide the conversation and uncover real needs.

“What would need to happen for this to be a no-brainer for you?”

“How does this align with your biggest priorities?”

2/ Implementation Questions 

Get them to troubleshoot and take ownership.

“Who else needs to be involved to make this run smoothly?”

“How do you see this playing out in six months?”

“What’s the easiest part of this to get wrong?”

3/ Time-Travel Questions 

Hold them accountable to past commitments without friction.

“When you agreed to X, what did you expect from us?”

“Looking back, what made you say yes in the first place?”

Engage with Labels

Instead of saying “Tell me more,” identify and verbalise emotions.

“That must have been exhausting for you.”

“Sounds like that was a major challenge.”

Example:

Statement: “Your offer is unrealistic.”

Response: “It seems like you have a reason for saying that.”

After using this phrase—stay silent. Let them fill the space.

Reframe the Loss

Fear of loss drives bad decisions. Flip the perspective.

“This didn’t work, but what’s the upside?”

Master the Tone

Low, slow, and calm prevents resistance.

A neutral tone keeps doors open. A sharp tone slams them shut.

Exit Without Burning Bridges

Leave the door open for future opportunities.

“Looks like our goals don’t align right now. Maybe in the future.”

“If more money wouldn't change how you spend your time, you're already rich.” Jack Butcher

Have a legendary week ahead. Stay strong.

Maxi | The Warrior’s Newsletter