Something You Should Know - SYSK TRENDING-How to Negotiate by Asking the Right Questions

Episode Date: May 5, 2026

For a lot of people, the idea of negotiating feels uncomfortable—something to avoid if possible. It can feel confrontational, awkward, or even risky. But what if negotiating didn’t have to be that way? What if it wasn’t about pushing harder or being more aggressive—but simply about asking better questions? It turns out that the most effective negotiators don’t rely on pressure or persuasion nearly as much as you might think. Instead, they guide conversations in a way that uncovers what really matters to the other person—and to themselves. And that shift can completely change the outcome. Alexandra Carter, Clinical Professor of Law and Director of the Mediation Clinic at Columbia Law School, has spent years teaching people how to negotiate more effectively. In her book Ask for More: 10 Questions to Negotiate Anything (https://amzn.to/2T6WaY8), she outlines a simple but powerful framework built around asking the right questions at the right time. In our conversation, she explains how this approach works, why it’s often more effective than traditional negotiating tactics, and how you can use it in everyday situations—from work conversations to personal decisions—without feeling uncomfortable or confrontational. PLEASE SUPPORT OUR SPONSORS AQUA TRU: Take the guesswork out of pure, great-tasting water. Head to ⁠https://AquaTru.com⁠ now and get 20% off your purifier using promo code SYSK. AquaTru even comes with a 30-day best-tasting water guarantee or your money back. POCKET HOSE: For a limited time, when you purchase a new Pocket Hose Ballistic, you'll get a FREE 360 degree rotating pocket pivot and a FREE thumb drive nozzle! Just text SYSK to 64000 RULA: This Mental Health Awareness Month, don’t just think about your mental health - actually take the step to take care of it. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Rula.com/sysk⁠⁠⁠⁠⁠⁠⁠⁠⁠ to get started. QUINCE: Refresh your everyday with luxury you will actual use! Go to ⁠⁠⁠https://Quince.com/sysk⁠⁠⁠ for free shipping on your order and 365-day returns. Now available in Canada, too! SHOPIFY: It's time to turn those "what ifs" into CHA CHING with Shopify Today! Sign up for your $1 per month trail and start selling today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://Shopify.com/sysk⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ PLANET VISIONARIES : We love the Planet Visionaries podcast! In partnership with The Rolex Perpetual Planet Initiative. Listen or watch on Apple, Spotify, YouTube or wherever you are listening to this podcast. Learn more about your ad choices. Visit megaphone.fm/adchoices

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Negotiation is everywhere, in politics, business, and in almost every part of our daily lives. When you think about negotiation, you might picture hard bargains, firm demands, and carefully crafted arguments. But what if the real power in negotiation isn't what you say, it's what you ask? And that's why today's SY-S-K trending topic is how to negotiate by asking the right questions. In my conversation with negotiation expert Alexander Carter, we'll discuss how the right questions can completely change the outcome of a conversation, whether you're negotiating a salary, resolving a conflict, or just trying to get to yes. So what should you be asking, and when, and how do you use questions to steer the conversation

in your favor? We'll find out right after this. RBC Training Ground has discovered potential in over 20,000 Canadian athletes and counting. Your story could be next. If you've got the drive, they'll help you find your path to the Olympics. Let's see what you've got. Sign up for free at rbc trainingground.ca. When you want something that someone else has, you negotiate to get it. That's how it all works.

We do it all the time, at work, at home. When you buy a car, you negotiate. It may not always feel like a negotiation. but it is. So how good you are at negotiating really matters. And here to make you better at it is Alexandra Carter. She is a clinical professor of law and director of the Mediation Clinic at Columbia Law School. And she spent the last several years helping thousands of people negotiate better, build relationships, and reach their goals.

She's the author of a book titled Ask for More, Ten Questions to Negotiate Anything. Welcome to something you should know. Thanks so much for having me. It's great to be here. I think a lot of people look at negotiating as a game, a game they're not particularly good at, and so they don't like playing it because they're not very good at it. And it can get messy, and it's just something we'd rather not do. How do you look at it? A lot of people, and this used to include me, think that it's just a back and forth over money.

And they can only negotiate well if they're senior business people or politicians or if they're the biggest, most aggressive person in the room. And that's the only kind of person who can really negotiate well. And I wanted to let people know that negotiation really is for everybody. And whether you're a management consultant, a mechanic, or a mom, you two can feel really confident doing it. Yeah, I like that biggest person in the room thing because I think there is a lot of intimidation, at least in people's perception about negotiation. The guy that can, you know, swing around in the room and be big is the person who often wins. Totally. And let me just tell you, I'm never the biggest person in the room. In fact, I'm five two in sneakers. They don't even see me coming. You know,

And what I want people to know is there's a different way that you can be an excellent negotiator. You don't have to go through life settling for less just because you're not the biggest, most aggressive person in the room. You can be really, really excellent at negotiation simply by asking the right questions. Well, before we get into the specific questions, I imagine there's something of a mindset that you approach. Like what's the goal? What are you trying to do with these questions to get where you want to go? It's really simple. Negotiation is just about steering relationships.

It's about teaching people how to value you from the first conversation you have all the way through the money conversations and beyond. And the other thing about steering relationships is, you know, what's the most important relationship of your life? it's the one you have with yourself. And I find that that is where negotiation has to start. You know, a lot of people think it starts from the moment you sit down with somebody else, and that's too late. You know, it starts by sitting down with yourself and asking the right questions so that you go into that negotiation with power. Power is actually not about bluster or aggression. Power is about knowledge. And the more you know about your and about your situation by raising the right questions, the more I have seen people go in

and perform with tremendous confidence. So let's talk about the 10 questions that you suggest people ask in a negotiation. The first five questions are what I call the mirror questions. And those are ones, as the name would suggest, where you are asking yourself. And it's five great questions that you can do in 30 minutes or less to really give you that incredible clarity and peace and perspective that you need when you're going in. And then the second five questions are the window questions. And those, you know, for your listeners, if anybody has ever gotten in a room with somebody else or sat down and blanked on what they wanted to say,

you're never going to do that again because you're going to have at your fingertips five great questions that are going to produce a lot of value in any conversation you have. So it's mirror and window. And so let's talk about some of the specific questions, starting with the mirror questions. What are they? A lot of times people assume, because I coach a lot of folks in negotiation, they assume that they need to start with the solution. Let's say you're sitting down with a contractor to talk about a bathroom renovation. And they think they should just go in and start talking about the numbers. That is not the question you need to ask. The first place to start every negotiation is asking this question, what's the problem I want to solve? We always have to

start by thinking about what it is that we're actually trying to accomplish. Let's take the bathroom, right? So let's say, for example, the problem you're trying to solve is that you're renovating your bathroom because you're going to sell your house. That is one set of decisions, right? Maybe you're putting stuff in there that you think other people will like. Or are you renovating the bathroom because you're going to live there for the next 30 years, or maybe even that your spouse had an accident and you need wheelchair access. In that case, thinking about the problem you're trying to solve, all of your decisions flow from that. So, whether you're talking to your child about screen time in the home, or whether you're negotiating for more salary, what's the problem I want

to solve is the first question you should ask. Great. So give me another one of the mirror questions. You know, a lot of times, especially during times of uncertainty or crisis, we're facing a situation and we're anxious about it. You know, maybe we're trying to negotiate for flex time, you know, or child care as, you know, companies return to work. Or maybe we've got issues in the home. And here's a question that I find helps people to gain that confidence. And the question is, how have I handled this successfully in the past? This is a great question to ask before you go into any conversation for two reasons. The first is that simply asking the question acts as what we call a power prime.

What does that mean? It means that simply by recalling a previous success before you go into negotiate, you are proven to perform better. There's been research to demonstrate it. The second reason to ask this really powerful question is that all, Oftentimes, when we look back at a prior success, this is a data generator. If we write down in detail strategies that we've used before, chances are that at least one of those is going to work for us again.

Now, I just want to answer a question that some of your listeners may be thinking, which is, you know, Alex, I've never dealt with coronavirus before, you know, or I've never been through this kind of a pandemic. And that's fine. None of us has. But I'm willing to bet that a lot of people have been through situations before where they had to pivot and adapt. Maybe it was 2008. Maybe it was another time, you know, in your business or in your life when you went through a time of uncertainty.

And so even if it's not exactly like this situation, look at something similar, write down what you did, and I know you're going to find something to help you here. All right. And so now you're primed and ready to go. You've done your inward thinking, and now you're going to go start negotiating with the other guy. And the first question, I'm going to tell you that people should ask on every occasion. It's kind of a trick because it doesn't have a question mark on it at all. It's two magic words, and those words are, tell me. You know, it's amazing to me that even as a conflict resolution expert and professional, a few years into my work, I was still coming home and asking my spouse or my child questions like, did you have a good day?

And when you ask somebody a question like that, whether it's an employee or somebody in your home, what's the answer that you're going to get? You know, usually it's a, huh, yeah, okay. You don't get a lot from that question. Similar to, you know, when you go in, let's imagine you're going to ask for more salary. And your first question is, can we increase me by 10%? Again, what are the possible answers to that? It's a yes or no. And when you ask somebody a yes or no question, what's the easiest thing for them to answer? No.

And so I want you to change that question. I want you instead to ask questions that start with tell me. Tell me how we can work together to get my compensation to the level that this position demands. Tell me what I need to do to demonstrate to you that I'm ready for the next level of management. Or even at home, you know, tell me, I've noticed you've been on your screens a lot today. Tell me more about what that's doing for you. You know, it sounds crazy, but that kind of question, even with a child, produces so much more. information than you would get by asking a closed question. When I learned how to start my conversations

with Tell Me, I made more deals, I had better relationships, and to be honest, you know, it affected even just the amount of, you know, peace and happiness I felt every day. Well, that's pretty powerful. I'm speaking with Alexandra Carter. She is author of the book, Ask for More, 10 questions to negotiate anything. So, Alex, when people talk about negotiating, it seems we're typically talking about money, how to pay less for something or how to get more out of someone. But I know you have examples of times when, yes, the money is important, but there are other things to work into the equation.

So the first time I ever negotiated for a speaking gig, I was a fairly young professor. And somebody approached me. It was the dad of one of the little babies that my daughter played with. And he said, we'd love to bring you in. So I negotiated with them. This was my first time. And pretty quickly, I maxed them out on the money. And I was convinced that they had given me all they could.

And so instead of seeing this as a win-lose, right? Either I need to get more money or this deal is done. I said, okay, tell me more about the event. They gave me a bunch of information, and I said, all right, here's what we're going to do. So you're going to pay me this fee, which is under market, but I'm going to do it if you can get me this. You've told me you have a professional photographer. I would like you to have that person take pictures of me with your company logo in the background while I'm on stage and give those to me to use for my portfolio. I'd also like to know a very senior department head who's willing to serve as a reference for me for my future engagements.

The value of those additional things turned out to be not only more than the difference between what they paid me and market value, but I went on to generate probably 50 times that in all of the referrals that I got from that one deal. So they got what they needed, which was a great speaker at an undermarket price, and I got what I needed. When you negotiate from your needs, you can create that mutual win. After you ask the tell me question, what's another one? So I think I just previewed it, but one of the questions I love is what do you need?

You know, I think a lot of times people assume that they have to come in. It's not just us. Sometimes the person on the other side assumes that they're going to have to come in with a full suit of armor and demand, demand, demand. When we ask people what they need, this question has an amazing way of, of kind of cutting through, you know, some of the, some of the BS that you were talking about, even in a situation where it's a car, you know, sale, I've gone in before and said, look, you know, I know you're a human being and I know a person, you know, you're a person who's trying to support your family also, right? I'm doing the same. So what do you need

to get this done, right? Here's what I need. I've told you my constraints. What do you need to show here to make this workable. And it's amazing how when you do that, it takes down some of the defensiveness and the person actually will, you know, give you a better deal or level with you about what it is they need to show. This can work with a car dealer. It's also great if you're working with a landlord during coronavirus, you know, asking them what they need, landlords have needs too. They may need not to have evictions. They may need to show occupancy. They may need to have some cash coming in the door, even if it's not the full amount of the rent. And so when you ask somebody what they need, you get the keys to the kingdom so that you can then, again, find that

target and hit it for a mutual win. One of the things that I think people feel they don't have the ability to do in negotiations that they see great negotiators do is keep their emotions out of it. They don't take it personally. You know what I mean? That a really good negotiator is a good negotiator and doesn't let feelings get in the way. Yeah, you know, feelings are really important. It's interesting because I think a lot of times people assume that they need to make decisions based only on facts, but actually research shows that for most of us, no matter how calm we think we are, emotions are how we make decisions. You know, advertising executives know this. They know that the way they can get people to spend their time and their money is by appealing to people's

emotions. But you're right, we don't want to get in the room and have our emotions get the best of us, right, so that we're not giving our best at the table. So here's how we do that. First, one of the questions in the mirror section asks people basically to write down how they feel because I found that if you're feeling anxious and you write that down, if you're feeling angry at somebody and you write that down, you know, if you grapple with it before you get in the room, rather than pretending you don't have emotions, you're going to do much better. You'll feel calmer. There's a way in which, you know, writing down what you feel ahead of time helps you release

it so that then you can get to the table and you also, you know what to do. We haven't really talked too much about tactics, negotiating tactics that you hear a lot about. And I don't know where you stand and which ones you use. But let me ask you about one. And that is the tactic of walking away. Walking away can be really effective when it comes from the right place. You know, for example, these are times when I might think about. walking away. I'm really clear on what I need, and it seems likely that we're not going to be

able to get there, at least for right now. Or, you know, let's say I'm getting what I would call some really unproductive behavior from the other person. You know, I help people resolve conflict in a lot of New York City courts. And so I've seen all sorts of, you know, interesting quote-unquote offers for how to for how to solve situations. If you get really, really challenging behavior from somebody else, you can also say, you know what, this isn't a productive conversation. And, you know, when you're ready to come back to the table and have something that's productive, I'm ready to talk. You know, for now I'm taking a break. So if your needs aren't being met, if somebody's unproductive or if they're emotionally overwhelmed. And just a

note on that right now during, you know, the pandemic, I'm finding that even very rational people can get emotionally overwhelmed. And so sometimes, I don't know that I would call it walking away. I think I would call it taking a break. Sometimes taking a break and letting somebody sit on something can be really helpful. So I get that. I get the taking a break thing, but I've often heard it argued that the strategy of getting up and walking away is telling the other person, hey, the deal is walking out the door. Maybe you need to change your mind a little bit here. And that it's a tactic to get people to kind of, it's like a slap in the face that the deal's about to end and that very often the deal changes. So in other words, you know, saying I'm going to

walk out as a way of communicating the winner. is closing. My preference would simply be to say, you know, instead of getting up and storming out, I like to be transparent and let people know what their window is. You know, like we have another couple of days that this proposal can work and after this time, it's not going to work anymore. Or, you know, I have a limited amount of time today. I've got 10 more minutes. And after that time, you know, I'm going to have to move on to my next meeting. It is absolutely true. You know, what you're talking about is called scarcity. And when people realize that your time or your money is a scarce resource, they may well be prompted to act. I am not a huge fan of tactics like

getting up and walking away from the table. I am a trust negotiator. I have found that when I level with my clients, when I level with the people that I'm negotiating with, when I simply tell them that something won't work for me and we need to try again, or that we're running out of time for one reason or another, if I do that from a place of integrity, I find that not only do I land that deal, but then people know they can trust me and they come back for the next one. And when I say I need something or we're out of time, it's not a tactic, it's the truth. And how do you deal with jerks? I would imagine working in the New York City court system that you come across the occasional jerk.

Uh-huh. Yep. And that brings with it a whole set of other problems, I suspect, because you're dealing with a big personality problem more than you may be necessarily dealing with the problem supposedly at hand. What's your attitude towards morons? you know, everybody is capable of having a bad day, I think is a good way to put it, but you're right. I've dealt with some really challenging behavior. And in fact, in the book, I talk about a situation where somebody said, you know, Alex, I've got an idea for what we can do here today. You can blank my blank. And suffice it to say, he was not suggesting that I read his proposal

or water his plants. Okay. So we get somebody who's really made an unproductive suggestion. And my tactic for that is I simply look at the person and say, how does blanking your blank help us here today? Right? I've had people say something like, I'm going to flip the table over. And I simply look at them and say, how is flipping the table over going to help you achieve your goals today? Deadpan, I don't react. I keep it calm. And I'm telling you that a lot of the time, when I ask people how that unproductive behavior is going to help them.

reach their goals, they can take a moment and they can recollect themselves. Sometimes that's enough to bring them back from the brink. But when it's not just a tactic like I'm going to turn the table over, but it's just a jerk in general who says, look, honey, this is how it's going to go and they try to intimidate you. How do you handle that? How do you respond to look, honey, this is how it's going to go. I did have somebody call me, honey, and I simply laughed and said, hey, that's my husband's name for me, so you're going to have to pick another. I use a lot of humor when I'm responding to people.

I try, first of all, to stay calm and be the grown-up, no matter what. And where I need to, I simply revert back to that's not going to help us here today. What you've told me is, you know, here's what your goals are, and here's what I'm telling you we need to get there. And I repeat and rinse and repeat as necessary. I stay calm. Sometimes I'll even summarize what they say. If they're going off on a ridiculous rant, I'll say, hold on a second. I just want to make sure I heard you right.

And I will repeat some of the ridiculous rant. It's amazing how sometimes when people have left their senses, They hear their own words played back to them, and it's kind of sobering. So I stay calm. I summarize. I repeat that that behavior is not going to help them get to the goal that they want. And then if it persists, I simply say, you know, thanks for your time. And when you're ready to have a more productive discussion, give me a call.

Well, I admire your thoughtfulness and self-control. I imagine that's come with a lot of practice. I've been speaking with Alexandra Carter. She's a clinical professor of law and director of the Mediation Clinic at Columbia Law School. And she's author of the book, Ask for More, 10 Questions, to Negotiate Anything. And you'll find a link to that book at Amazon in the show notes for this episode. Thanks, Alex. All right.

Well, thanks so much. I hope this was helpful. Thank you for listening to this S-Y-S-K trending episode on The Art of Negotiation. and feel free to share this with someone you know. I'm Micah Rothers. Thanks for listening today to Something You Should Know.