How To Win Any Negotiation Without Being Pushy (Lessons From An FBI Hostage Negotiator)

I’ve always been terrible at negotiation.

No matter how hard I try, I’d end up handing over a better deal to the other person. 

I was desperate to find a book or a mentor who could teach me the art of negotiation.

Luckily, I stumbled upon a game-changing book written by one of the best negotiators in the world.

The author, Chris Voss, is an ex FBI Hostage Negotiator. And the book is packed with powerful questions designed to shift the dynamics of any negotiation.

Let me break it down for you…

In any negotiation, you’ve two choices.

1. Ask close-ended questions and expect a straight yes or no

2. Ask open-ended questions (Also known as calibrated questions)

According to Chris, “Calibrated questions are not just random requests for comment. They have a direction: once you figure out where you want a conversation to go, you have to design the questions that will ease the conversation in that direction while letting the other guy think it’s his choice to take you there."

You’ve to calibrate them carefully, just like you would calibrate a gun sight or a measuring scale, to target a specific problem.

The best thing about calibrated questions is the power to educate your counterpart on what the problem is rather than causing conflict by telling them what the problem is.

Now, Chris has been in some of the toughest negotiations. He has delt with kidnappers, terrorists and criminals. And he has a solid sent of calibrated questions to ask in negotiations.

These are some of the best-calibrated questions to ask:

What about this is important to you?

This helps you find out what really matters to them. It keeps the focus on their priorities, not just their demands.

How can I help to make this better for us?

This shifts the conversation from “me vs. you” to “us.” It makes them more willing to find a solution that works for both sides.

How would you like me to proceed?

This puts the responsibility on them. It makes them think of a realistic way forward.

What is it that brought us into this situation?

This helps you understand the real reason behind the problem. When you know the cause, you can negotiate better.

How can we solve this problem?

This makes them part of the solution. People are more likely to agree when they help create the outcome.

What’s the objective / what are we trying to accomplish here?

This keeps the focus on the main goal. When both sides remember the bigger picture, it’s easier to find common ground.

How am I supposed to do that?

This is a smart way to push back without saying "no." It forces them to rethink their position and consider your limits.

Abdul Kader

Today’s edition of The Book Nerd is written by Abdul Kader. If you want to contribute, apply here.

The Book Nerd is all about breaking down the best ideas from books on psychology, productivity, business, marketing, biographies, tech, AI, automation, and self-improvement.

If you have a great book recommendation in these areas, let me know!

I’m also accepting contributions! If you’ve read a book that had a powerful insight or actionable takeaway, I’d love to feature it—with full credit to you. No need for a full summary—just a short write-up on one key idea that stood out to you. I might edit for clarity, but your core ideas will stay the same. If you're interested, apply here!

And if you found this newsletter valuable, share it with a friend who loves learning as much as you do. I appreciate it!