Ask for More: 10 Questions to Negotiate Anything

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How can asking better questions lead to better outcomes in negotiation, career, and life?

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How can asking better questions lead to better outcomes in negotiation, career, and life?

Image courtesy of interviewee. January 16, 2025

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In this text, the speaker shares their journey of redefining negotiation beyond traditional views of mere haggling, emphasizing it as a process of "steering" relationships. The transformative moment occurred during a honeymoon kayaking trip when the speaker recognized that negotiation is about guiding discussions rather than just persuading others.

The speaker highlights the importance of asking open-ended questions to foster collaboration and gather information effectively. This video approach, which includes self-reflection through "mirror questions" and initiating conversations with "window questions," allows negotiators to build trust and understand the other party's perspective better.

Additionally, the speaker critiques conventional negotiation methods that focus on the act itself rather than the preparatory work and personal insights that precede a negotiation. They stress the significance of authentic negotiation, where the individual’s true self contributes to more productive and successful outcomes.

Overall, the text advocates for a paradigm shift in how negotiation is understood and practiced, emphasizing inquiry and relationship-building over confrontation. The speaker concludes that effective negotiation can lead to not only financial success but also greater clarity and satisfaction in both personal and professional lives.

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Here are five key points derived from the video:

1. **Redefining Negotiation**: The author emphasizes a broader understanding of negotiation beyond mere haggling over money. Instead of viewing negotiation as a reactive process, they propose that it can be a proactive way to steer relationships in both personal and professional convideos.

2. **Importance of Open-Ended Questions**: The author advocates for the use of open-ended questions as the most effective tool for negotiation. These questions foster collaboration and trust, enabling both parties to work together toward mutually beneficial outcomes.

3. **Preparation and Self-Reflection**: A critical aspect of successful negotiation is self-reflection and preparation, termed the "mirror" phase. Understanding one’s own goals and emotions before entering a negotiation is essential for clarity and effectiveness.

4. **Counterintuitive Strategies**: The video highlights that the most effective negotiation methods, such as asking diagnostic questions, differ from conventional beliefs that emphasize persuasive speaking. This approach can lead to better relationships and outcomes.

5. **Widely Applicable Skills**: The skills and techniques discussed are applicable not only in formal negotiation scenarios but also in everyday interactions. The author stresses that authentic negotiation, rooted in self-awareness and open dialogue, can enhance both career satisfaction and personal relationships.

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Here are key quotes extracted from the video you :

1. **Redefining Negotiation**: "I thought to myself, that's right. I've never heard anyone use the word that way before, kayak toward a beach? I'm steering."

2. **Negotiation as Steering**: "What would my life look like professionally and personally if I saw negotiation simply as steering the process of steering my relationships?"

3. **Essential Questioning**: "The best way to negotiate is by asking open-ended questions and asking them first before we get to the persuasion."

4. **Mirror Questions**: "These are questions that we ask ourselves before we sit down with anyone else and getting clear on our own goals, our own needs, our own emotions... is critical for being able to arrive at the table with clarity and command."

5. **Window Questions**: "The window questions quite simply are a way to open up a conversation on any topic."

6. **Gathering Information**: "It is about gathering information, building trust, and starting to work our way toward figuring out what is the bullseye of that optimal solution going to be for us both."

7. **Importance of Preparation**: "One, most books start in the wrong place. They start at the moment one arrives at the negotiating table, and that is too late."

8. **Looking in the Mirror**: "If you don't look in the metaphorical mirror, you're going to have what I call a one car accident. In negotiation, you're gonna get in your own way."

9. **Negotiation with Fear**: "Most people approach negotiation with some fear... over 50% of people did not negotiate their last salary."

10. **Building Trust**: "When we have the best information and when we cultivate trust, that creates the best deals."

11. **Authentic Negotiation**: "If you negotiate authentically from the best of who you are, that's when you're going to be your most effective."

12. **Personal Anecdotes**: "It was critically important to me in ask for More, to include not just professional anecdotes, but personal anecdotes."

13. **Open-ended Questions Leading to Success**: "The long-term impacts of redefining negotiation and asking powerful, open-ended questions are too vast to explain... the more open-ended questions you asked, the more money you made."

These quotes encapsulate the core ideas about negotiation that the speaker presents, emphasizing the importance of perspective, preparation, and the art of questioning in effective negotiation.

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When I was in law school

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and even as a young lawyer, I had absorbed this definition

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of negotiation that basically meant a back

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and forth haggling process to get to an agreement,

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usually over money.

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And I remember thinking that this seemed frankly like narrow

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and reactive almost

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as though we only negotiate when the circumstances

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force it upon us, right?

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Like, you know, few times a year when we're signing a

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retainer agreement or inking an m and a deal

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or whatever it might be.

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And then I went on my honeymoon to Hawaii,

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I married another lawyer,

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and unexpectedly it was on that honeymoon

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that I completely redefined what negotiation meant.

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The two of us got in a kayak on the Y Lua River

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and our guide up ahead turned back

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and said, okay folks, let's negotiate these things

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to the left because we're gonna hit that beach up ahead.

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And in that moment I thought to myself, that's right.

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I've never heard anyone use the word that way before,

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but what am I doing when I'm negotiating my

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kayak toward a beach?

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I'm steering. And in that moment, as a burgeoning academic

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and as a practicing lawyer, I thought,

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what would my life look like professionally

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and personally if I saw negotiation simply as steering

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the process of steering my relationships?

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And what if I steer

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so effectively in those everyday conversations

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that then when we get to a pivotal conversation,

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a difficult conversation, a money conversation,

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we're gonna be so much more successful together

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because we have intentionally steered this relationship

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through all of those everyday negotiations.

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Negotiation is steering. What's the best way to steer?

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And the answer is somewhat counterintuitive.

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A lot of folks that I've taught negotiation to believe

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that negotiation is coming in

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and having the most persuasive way to make your points,

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and I tell them, that's actually not negotiation,

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that's public speaking.

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It turns out that research study

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after research study has shown there is one single

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underutilized tool that it takes minutes to prepare

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seconds to execute.

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And the more you do it, the more money you make

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and the better the relationships you have.

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The best way to negotiate is by asking open-ended questions

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and asking them first before we get to the persuasion,

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before we say, but here's what I'm here to talk about.

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Asking those diagnostic open-ended questions is the single

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best way to recruit the other person to your team so

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that you are now co-conspirators working

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toward the same goal.

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So in ask for More,

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I lay out a framework that has two types of questions.

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The first type is what I call mirror questions.

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These are questions that we ask ourselves

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before we sit down with anyone else

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because that work of interrogating ourselves

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and getting clear on our own goals, our own needs,

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our own emotions, even as we negotiate, is critical

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for them being able to arrive at the table

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with clarity and command.

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Then once we're sitting down with somebody else virtually

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or in person, the second type

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of question is called the window question.

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And these are the single best questions I have found

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for any negotiation that will start you off on a great foot.

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They will get you the most information.

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They will lay the groundwork for that relationship

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and collaboration and they create the best deals.

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The window questions quite simply are a way

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to open up a conversation on any topic.

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If one is sitting down to negotiate a contract, I start with

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what I call my two magic words.

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Tell me, tell me your views on the contract.

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Tell me what you're trying to do in your business.

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Tell me the best ways we can work together.

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Tell me is actually technically not a question.

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It is in the imperative mood.

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It is a command, but it reads as a question

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and it's the one that gets you the most information.

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Other than that, other questions that are proven

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to open up a dialogue

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and really start getting to those, the fruit, right,

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and those solutions that are gonna be lucrative

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for both people are questions, starting with what

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or how, right?

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So what are your needs? What are your concerns?

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How might we best shape those together?

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These are questions that are not capable of being answered

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with a yes or a no.

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And once again, this is about steering.

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It is not about forcing,

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which actually is counterproductive in negotiation.

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It is about gathering information, building trust,

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and starting to work our way toward figuring out

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what is the bullseye of

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that optimal solution going to be for us both.

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What I found about traditional methods is two things.

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One, most books start in the wrong place.

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They start at the moment,

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one arrives at the negotiating table, and that is too late.

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In my role as a professor at Columbia Law School,

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I have helped many thousands of people,

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incredibly brilliant, credentialed, experienced people,

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negotiate deals and get out of conflict situations.

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And what I have found is that people don't do the work

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before they get to the table.

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That's gonna help them get the most of

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that conversation once they do. So

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Most books are not getting to what I call the mirror,

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which is frankly the most critical part of the negotiation.

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If you don't look in the metaphorical mirror, you're going

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to have what I call a one car accident.

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In negotiation, you're gonna get in your own way.

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We've seen some of our leaders, whether business

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or political, have those one car accidents.

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But then secondly,

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I hadn't found another source either in academic material

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or elsewhere in popular material

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that really explored the full power of open-ended questions.

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What they are, what they are,

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not simple rules about how to ask them.

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And then walking you through step by step what each one

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of these questions is designed

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to do from a research perspective

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and how it can work either in the classroom or in real life.

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Most people approach negotiation with some fear

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and maybe even ready to fight.

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In fact, this misconception about what negotiation is

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or what it can be leads a lot of people either

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to negotiate ineffectively or not to do it at all.

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Recent research shows that over 50%

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of people did not negotiate their last salary.

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We are either under negotiating

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or we are negotiating poorly.

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When you come to the table

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and defy expectations by saying, I'm here to get to know you

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and your business a little bit better, tell me more about

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what you're hoping to do in the market.

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Tell me some of the ways

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that maybe my predecessors have worked with you

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that haven't been productive or haven't served your needs.

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This is disarming.

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It makes the person see we're gonna be doing this a

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different way and it lays the foundation, right?

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Again, research shows that when we have the best information

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and when we cultivate trust, that creates the best deals.

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So when you come in with open-ended questions,

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you defy societal expectations.

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You cause the other person

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to realize we're actually gonna have a different type

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of conversation here.

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And you pave the way for extraordinary results.

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It was critically important to me in ask for More,

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to include not just professional anecdotes,

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but personal anecdotes.

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And there's a reason for that.

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Number one, when I teach in the classroom at Columbia,

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I encourage students to come into the

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classroom as whole people.

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We really need to cultivate the ability

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to self-reflect in order

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to be the very best negotiators we can be.

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And self-reflection

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and negotiation means the entire world is your laboratory.

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We are negotiating all the time,

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and I find that the way we negotiate at home

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is often the way we negotiate at the office.

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And what I want to encourage is what's backed by research,

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which is if you negotiate authentically from

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the best of who you

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Are, that's when you're going to be your most effective.

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And I want to help lawyers

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and professionals of all kinds create the kind of lives

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that will support both career and home.

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So also, when I teach in the classroom at Columbia, I found

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that the didactic principles are what they are.

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I do my best to present them in a sparkling, a manner

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as possible, but the anecdotes are what make them stick.

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The anecdotes show you the way

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and the anecdotes give you hope

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because so much of

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what we see in popular media about negotiation

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is really not representative of what it can be.

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And I wanted people through ask for more to understand,

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you can do this a different way.

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There are people including me doing this work out there

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and look at the results.

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You can achieve. The long-term impacts of

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redefining negotiation

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and asking powerful, open-ended questions are

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too vast to explain in a 20 minute interview,

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but they would include much more career satisfaction,

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greater clarity on one's path in life.

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Much, much more money studies shown,

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including a study just this year that came out,

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analyzing 60,000 human interactions through AI showed

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that the more open-ended questions you asked,

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the more money you made,

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and people who did this effectively

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made 20% more at least.

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And so that's a compelling result from asking

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open-ended questions.

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But I would also say that questions

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are like the lens of a camera.

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And if we want to be problem solvers

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and innovators, then we wanna open that aperture

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and get the greatest possible view

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on the problems facing us in our time.

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And innovation is problem solving writ large.

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We do that by solving the right problem that is entirely

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through asking the appropriate questions.

Redefining Negotiation: Steering Relationships

00:00:00 - When I was in law school and even as a young lawyer, I had absorbed this definition of negotiation that basically meant a back and forth haggling process to get to an agreement, usually over money. And I remember thinking that this seemed frankly like narrow and reactive almost as though we only negotiate when the circumstances force it upon us, right? Like, you know, few times a year when we're signing a retainer agreement or inking an m and a deal or whatever it might be.

00:00:34 - I married another lawyer, and unexpectedly it was on that honeymoon that I completely redefined what negotiation meant. The two of us got in a kayak on the Y Lua River and our guide up ahead turned back and said, okay folks, let's negotiate these things to the left because we're gonna hit that beach up ahead. And in that moment I thought to myself, that's right. I've never heard anyone use the word that way before,

00:01:06 - kayak toward a beach? I'm steering. And in that moment, as a burgeoning academic and as a practicing lawyer, I thought, what would my life look like professionally and personally if I saw negotiation simply as steering the process of steering my relationships? And what if I steer so effectively in those everyday conversations that then when we get to a pivotal conversation,

Redefining Negotiation: The Power of Open-Ended Questions

00:01:40 - we're gonna be so much more successful together because we have intentionally steered this relationship through all of those everyday negotiations. Negotiation is steering. What's the best way to steer? And the answer is somewhat counterintuitive. A lot of folks that I've taught negotiation to believe that negotiation is coming in and having the most persuasive way to make your points,

00:02:10 - that's public speaking. It turns out that research study after research study has shown there is one single underutilized tool that it takes minutes to prepare seconds to execute. And the more you do it, the more money you make and the better the relationships you have. The best way to negotiate is by asking open-ended questions and asking them first before we get to the persuasion,

00:02:43 - Asking those diagnostic open-ended questions is the single best way to recruit the other person to your team so that you are now co-conspirators working toward the same goal. So in ask for More, I lay out a framework that has two types of questions. The first type is what I call mirror questions. These are questions that we ask ourselves before we sit down with anyone else

Mastering Negotiation Through Clarity and Open-Ended Questions

00:03:15 - and getting clear on our own goals, our own needs, our own emotions, even as we negotiate, is critical for them being able to arrive at the table with clarity and command. Then once we're sitting down with somebody else virtually or in person, the second type of question is called the window question. And these are the single best questions I have found

00:03:47 - They will get you the most information. They will lay the groundwork for that relationship and collaboration and they create the best deals. The window questions quite simply are a way to open up a conversation on any topic. If one is sitting down to negotiate a contract, I start with what I call my two magic words. Tell me, tell me your views on the contract. Tell me what you're trying to do in your business.

00:04:17 - Tell me is actually technically not a question. It is in the imperative mood. It is a command, but it reads as a question and it's the one that gets you the most information. Other than that, other questions that are proven to open up a dialogue and really start getting to those, the fruit, right, and those solutions that are gonna be lucrative for both people are questions, starting with what

Steering Negotiation: The Power of Open-Ended Questions

00:04:47 - So what are your needs? What are your concerns? How might we best shape those together? These are questions that are not capable of being answered with a yes or a no. And once again, this is about steering. It is not about forcing, which actually is counterproductive in negotiation. It is about gathering information, building trust, and starting to work our way toward figuring out what is the bullseye of that optimal solution going to be for us both.

00:05:22 - One, most books start in the wrong place. They start at the moment, one arrives at the negotiating table, and that is too late. In my role as a professor at Columbia Law School, I have helped many thousands of people, incredibly brilliant, credentialed, experienced people, negotiate deals and get out of conflict situations. And what I have found is that people don't do the work

00:05:51 - That's gonna help them get the most of that conversation once they do. So Most books are not getting to what I call the mirror, which is frankly the most critical part of the negotiation. If you don't look in the metaphorical mirror, you're going to have what I call a one car accident. In negotiation, you're gonna get in your own way. We've seen some of our leaders, whether business or political, have those one car accidents. But then secondly,

Unlocking Effective Negotiation through Open-Ended Questions

00:06:25 - or elsewhere in popular material that really explored the full power of open-ended questions. What they are, what they are, not simple rules about how to ask them. And then walking you through step by step what each one of these questions is designed to do from a research perspective and how it can work either in the classroom or in real life. Most people approach negotiation with some fear

00:06:56 - In fact, this misconception about what negotiation is or what it can be leads a lot of people either to negotiate ineffectively or not to do it at all. Recent research shows that over 50% of people did not negotiate their last salary. We are either under negotiating or we are negotiating poorly. When you come to the table and defy expectations by saying, I'm here to get to know you

00:07:27 - what you're hoping to do in the market. Tell me some of the ways that maybe my predecessors have worked with you that haven't been productive or haven't served your needs. This is disarming. It makes the person see we're gonna be doing this a different way and it lays the foundation, right? Again, research shows that when we have the best information and when we cultivate trust, that creates the best deals. So when you come in with open-ended questions,

Redefining Negotiation Through Personal Authenticity

00:08:00 - You cause the other person to realize we're actually gonna have a different type of conversation here. And you pave the way for extraordinary results. It was critically important to me in ask for More, to include not just professional anecdotes, but personal anecdotes. And there's a reason for that. Number one, when I teach in the classroom at Columbia, I encourage students to come into the classroom as whole people. We really need to cultivate the ability to self-reflect in order

00:08:31 - And self-reflection and negotiation means the entire world is your laboratory. We are negotiating all the time, and I find that the way we negotiate at home is often the way we negotiate at the office. And what I want to encourage is what's backed by research, which is if you negotiate authentically from the best of who you Are, that's when you're going to be your most effective. And I want to help lawyers

00:09:05 - that will support both career and home. So also, when I teach in the classroom at Columbia, I found that the didactic principles are what they are. I do my best to present them in a sparkling, a manner as possible, but the anecdotes are what make them stick. The anecdotes show you the way and the anecdotes give you hope because so much of what we see in popular media about negotiation

Revolutionizing Negotiation: The Power of Open-Ended Questions

00:09:36 - And I wanted people through ask for more to understand, you can do this a different way. There are people including me doing this work out there and look at the results. You can achieve. The long-term impacts of redefining negotiation and asking powerful, open-ended questions are too vast to explain in a 20 minute interview, but they would include much more career satisfaction,

00:10:08 - Much, much more money studies shown, including a study just this year that came out, analyzing 60,000 human interactions through AI showed that the more open-ended questions you asked, the more money you made, and people who did this effectively made 20% more at least. And so that's a compelling result from asking open-ended questions.

00:11:04 - are like the lens of a camera. And if we want to be problem solvers and innovators, then we wanna open that aperture and get the greatest possible view on the problems facing us in our time. And innovation is problem solving writ large. We do that by solving the right problem that is entirely through asking the appropriate questions.

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