Leap Academy with Ilana Golan
Alex Carter: Negotiate Like a Pro, Powerful Techniques to Unlock Career and Business Growth | E99
Thu, 24 Apr 2025
As a shy kid, Alex Carter struggled to speak up for herself. Her parents’ divorce sparked her interest in advocacy and mediation, which led her to pursue a law degree. Despite facing self-doubt early in her career, Alex bet on herself and built a career as a Columbia Law professor and renowned negotiation expert. Now, she helps others find their voice, advocate for themselves, and unlock career success. In this episode, Alex joins Ilana to share actionable strategies for negotiating with confidence, landing promotions, charging your worth, and scaling a business. Alex Carter is a negotiation expert, Columbia Law professor, and bestselling author. She specializes in helping professionals and entrepreneurs build the confidence to negotiate effectively in high-stakes situations. In this episode, Ilana and Alex will discuss: (00:00) Introduction (01:49) Finding Her Voice and Building Confidence (06:56) Pursuing a Career in Law and Mediation (10:52) Betting on Yourself Despite Self-Doubt (14:25) The Power of Negotiating for Yourself (19:48) How to Secure Your First Big Client (24:39) Negotiating Your Way to Career Success (30:41) Key Steps in Preparing for a Negotiation (39:36) Face-to-Face vs. Email Negotiations (41:44) Negotiating Across Cultures (43:06) Practical Solutions to Business Challenges (45:52) How to Scale by Leveraging Your Time Alex Carter is a negotiation expert, Columbia Law professor, and bestselling author. She specializes in helping professionals and entrepreneurs build the confidence to negotiate effectively in high-stakes situations. With a background in law and mediation, Alex teaches practical strategies for securing promotions, landing clients, and navigating complex negotiations. Her work empowers individuals to advocate for themselves and achieve career success. Connect with Alex: Alex’s Website: alexcarterasks.com Alex’s LinkedIn: linkedin.com/in/alexandrabcarter Resources Mentioned: Alex’s Book, Ask for More: 10 Questions to Negotiate Anything: https://www.amazon.com/Ask-More-Questions-Negotiate-Anything/dp/1982130482 Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Chapter 1: Who is Alex Carter and what is her expertise?
I see negotiation as problem solving. I don't sell, I problem solve.
Alex Carter, she is a Wall Street Journal bestselling author, Columbia Law professor, the go-to expert for negotiation.
Earlier on in my career, I was for everybody else, the fearless junkyard dog negotiator who would just go out and get what you needed. And when it came to me, I would hesitate.
When you get to that place where you are so rock-solid confident in your worth that you're able to say, here's the investment to work with me, and if that doesn't work for you, I understand, and you believe it, people smell that on you. Negotiation does not start with the numbers.
It starts with using your words to teach people how to think about you and the value you bring long before you get to the numbers. These are the questions that research shows make people the most money.
Alex Carter, the go-to expert for negotiation. She is a Wall Street Journal bestselling author, Columbia law professor, and her recent TEDx on how to ask for more, highly recommend, check it out, was seen by over a million people. She built a career helping people own their voice and ask for more, which is so, so, so important.
Alex, you also say negotiation isn't just for the boardroom, it's for life. I'm so glad that you're here today.
Oh, Ilana, thank you for having me. I'm so excited for the conversation.
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Chapter 2: How did Alex Carter find her voice and build confidence?
It's going to be incredible, but I want you to take us back in time to Alex, the kid, how you grew up, where did you grow up? How were you as a kid where you were like this assertive, like I can negotiate anything in life?
So interesting. I think people, Ilana, often assume that I came out of the womb asking for more, right? That I felt so confident from a very early age, always to get what I needed and to use my voice. And the truth is that actually, as a younger kid, I was quite shy, especially in school or outside the home.
I was really into reading, really into academics, but I often felt as though in larger groups, I wasn't speaking up as much. And then I remember the moment in eighth grade that they started introducing us to speech and debate.
And that's when I figured out that when I had something substantive to say, I felt very comfortable getting up, speaking on my feet, and saying it to an audience of any size. And that was a really interesting lesson for me, really knowing more about what I was interested in. substantively helped me find my feet and my confidence. It makes me think about your audience, right?
Of entrepreneurs and folks who, when you get on your topic or your mission, all of a sudden you're unstoppable and you have something to say. And later on, Ilana, I found that I started getting more comfortable using my negotiation skills for other people.
We can get into this, but earlier on in my career, really, I was for everybody else, the fearless junkyard dog negotiator who would just go out and get what you needed. And when it came to me, sometimes I would hesitate.
I want to go there in a second because I think that selling yourself, selling your value, negotiating, we'll talk about it because you don't call it selling for a good reason. But selling yourself, selling your value slash negotiating, I'm saying what people perceive of the words. Are you going to correct us? Yes, uh-huh. But the way it's looking right now, people hesitate, right? It's scary.
I don't want to push. I don't want to be the person that rubs them in the wrong way, the rock the boat. So we'll talk about this. But I would love to understand, and I think you said something beautifully, that when you find your voice... you are so much more in power and empowered to actually speak up, right? Which I think is so, so, so important.
But I do want to challenge you for a second, because when you didn't know if you have your voice, why did you go to debate? Why did you go in high school to some kind of public speaking team? How did you push yourself? Did somebody else push you? What was it?
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Chapter 3: What inspired Alex to pursue a career in law and mediation?
And I have to say, it took a couple of people close to me to say, sit down, you can do this. And so when I wrote that application, I focused on what I did have. I knew I was going to be one of the youngest and least experienced people in the pool. I applied for a full-time law teaching job when I had no law teaching experience.
But what I did have was substantial experience teaching in other contexts. What I did have was that I had been through the program as a student, and so I felt I was closer to what the students needed and would be looking for, and I would know how to craft a curriculum for them. And I flat out told people when they interviewed,
If you're looking for the most experienced person in the pool who's going to lead your program for the next 10 to 15 years before they retire, I'm not that person. If you are looking for somebody with vision and energy and a lot of ideas who could take your program to the next level for 30 years and beyond, I'm who you want. And the committee decided that's what they wanted.
So truly, I always tell people, bet on yourself, start with what you have. And now since then, I've taken a number of leaps where people called me and said, can you do this? And I had never done it before. And I thought to myself, yes, I can. And so I went ahead and did it.
you're never going to be perfectly ready. It's never realistic because as high achiever, you're always pushing yourself a little beyond when you're really ready. But you're bringing that conviction of why it will work versus why it won't. And I think that's just beautiful. And you share a lot around how do you... decide to go even if you're not ready. And how do you push through that?
And I just love that, right? I think you did it also with a clinic in Colombia, a negotiation clinic. You've done it with the UN. I want to talk about it for a little bit. So you've done it again and again, even though you're never going to tick all the boxes. It's just not realistic.
No, it's not realistic for anyone. And I'll tell you now, as somebody who hires people, I interview potential professors for positions. One of the things I'm looking for is somebody who's clear on what they have left to learn. How do they want to grow? what are the skill sets and the competencies they want to develop.
Far from showing a lack of confidence, to me, that is the most confident person in the pool because they're coming in clearly understanding their expertise and also with the comfort and the command to be able to say, and here's where I want to grow. Because as you said, top performers are always looking to grow.
The most dangerous person for me in a pool of applicants is the person who says, I know it all. No, you don't.
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Chapter 4: How did Alex overcome self-doubt and bet on herself?
So I asked them a couple questions. I said, tell me how you're documenting the event. And they said, we're having a professional photographer and videographer. And I said, okay, tell me who's going to be at the event. And they told me all the managing directors who were going to be there. And I said, fine, okay.
I'm going to do this slightly below market for the max you've told me you can offer me. Plus, I want a certain number of digital photos of me in front of your company's logo that I have permission to use for my speaking portfolio.
And if I blow the doors off it like I'm confident I'm going to, I'd like to have several high-level managing director people be references for me for other future clients." I went on, Ilana, from that one gig, okay, where I got up there and for a second I thought, oh my God, what am I doing? I'm in front of like these very senior people.
And then I thought, okay, I'm just going to do what I know I can do. Blew the doors off it. I ended up over the next few years going on to make like 20 to 25 times what I did in that one engagement just from referrals, referrals, referrals, referrals. And I built from there. So it started with taking a leap. It started with betting on myself.
But I also brought a really high level of excellence to every job I did. And I treated it, I treated the keynote like a negotiation because I see negotiation as problem solving. I don't sell. I problem solve. I serve people. And I tried to serve each one of my clients at a really high level because I knew that then somebody else was going to pick up the phone and call me. And that's what happened.
For everybody listening, first of all, I want to iterate the hidden market, right? One of the big things that we say in Leap Academy is that every great opportunity you're ever going to get is going to happen from the hidden market. It's not in the job board. It's really who knows you, who thinks about you when you're not in the room, who's going to bring this opportunity for you.
Alec, this is classic, right? I mean, they've seen you, they whatever, right? And again, you need to be top of mind. Otherwise... Who's going to see you, right? That's how they reach out to you. But also I love, and you have it also in the book, there's other things you can negotiate. It's not only money.
In this case, it was whatever, success stories, leads, media, because now you can use it for your website, for your reels. Like it's just so powerful because there's other things that you can negotiate and you look at it as problem solving, which is so brilliant. Talk to us a little bit more about our listeners.
This will be really impactful for them because they might need to negotiate a job, a paternity or a role. What are some of the tools? And you have some amazing tips in your book, Ask for More. What are some of the biggest advice that you would give to some of these people?
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Chapter 5: Why is negotiating for yourself so powerful?
And when you ask a yes or no question, what is the easiest answer for somebody to give you? No, no, no. So instead, I like people to ask questions, and I have three magic ways that you can formulate what I call an open or a diagnostic question. These are the questions that research shows make people the most money, and they compel someone to give you a lot of information.
So instead, you should be asking what, how, and my favorite two magic words, tell me. So Ilana, what are the criteria for promotion? Or Ilana, what is the process for promotion this year? How? Ilana, how can we work together to make the case? How can I help you with data or other evidence to show that this is the year I'm going to be promoted? And finally, it could be
Tell me when the next time is that we should have this conversation. Tell me the format you'd like me to put together this information in. Tell me who else is involved in the decision that I might want to speak to. Tell me about the process. Those are questions that show command, they show leadership, they show collaboration, and they're impossible to say no to.
That was so, so, so powerful. Listeners, I want to make sure that you understand it. Every single thing Alex said is from the eyes of the person she's talking to, right? It's not about you. It's about them. It's about making them successful and how it's the win-win.
And what I love about what you say, Alex, is also how you steer the conversation, how you create that curiosity, ask a lot of questions, but you also say something really, really fundamental in your book and your TEDx. And you're actually taking them back and saying it all starts way before the negotiation. And it actually starts with you because it's so true, right?
We take ourselves out of the race way ahead of time.
Yes. The first half of Ask for More is the section that I call the mirror. And this is the section where we start the negotiation. Most of the time, people think negotiation starts from the moment that you and I are sitting down together and talking about my request for a promotion, but it doesn't.
negotiation starts at home with you, with that individual person and looking in the metaphorical mirror to ask yourself a few great questions so that you can go into that negotiation with the other person from a place of total clarity, total confidence, total command. So what does that look like? When I sit down with myself, I'm asking myself a few questions.
First of all, I'm thinking about, okay, What's the problem I want to solve in what I'm about to ask Ilana for? Maybe I'm asking for this promotion because I want to show Ilana that I'm on a trajectory for the top. This promotion is part of where I want to go for the company.
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Chapter 6: How did Alex secure her first big client and build her speaking career?
If you think it's going to be very emotionally charged and that you're going to be able to put your points more linearly and say things the way you want to say them with space to do so, email can be good. I've counseled a number of people who are negotiating severance who felt like it was too much to be on the...
phone or on Zoom with someone and email allowed there to be some distance so that you could take a pause and really think about how to put your best foot forward. Most of the time, big fan, like you said, of the in-person or face-to-face, there are times when email can be very useful.
That's super interesting for me to hear. I think as an Israeli, I'm a little too blunt in emails. I should probably do it.
I have to tell you, can I just say, one of the fascinating things I find about negotiation is how different it can be jurisdiction to jurisdiction. And so this very successful German entrepreneur I know said, Alex, I just have a way of putting things sometimes that is not conducive.
to negotiation, she actually writes up the email and then puts it into an AI tool and says, do the following things to this. And she said, so they massage some of my language and then I'm able to send that out and not sound like I'm quite so strident. So... There are lots of tools out there now for you to put your best foot forward, but it's also a lesson to your global audience.
Know who you're negotiating with. I've worked with a number of Israeli professionals, and I'm originally from New York. We are both delightfully direct, right? And there's something that's wonderful about that. When I negotiate in other jurisdictions, like maybe in certain East Asian jurisdictions or certain African jurisdictions— So different people are a little bit more indirect.
And so I have to think about not that my way should always be right, but how can I negotiate in a way that's going to feel appropriate for that person and they're going to be able to hear me.
Alex, I love, love, love, love, love this. What are some challenges that maybe you went through as sort of an entrepreneur that you feel sharing will actually really help our audience?
Some of the problems I went through initially counting myself out because looking at the market out there and saying, well, maybe, honestly, I'm a woman in a male-dominated field and I'm a little younger. I'm not that young, Ilana. I cover my gray hair. But I'm still a little bit younger than perhaps your average negotiation keynote speaker out there.
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Chapter 7: What negotiation strategies can help you succeed in your career?
I really wish I had known that who I am is more than enough. I think like a lot of perfectionists, I always think about, well, I did that yesterday. What have I done today? Every day I wake up and I think I'm behind who I am. I don't need to be someone else. I am really powerful as I am. Just like every single person in this audience, you are powerful just as you are.
And I used to have a bit of, I hate this term, imposter syndrome. I just like to think of it as your psyche hasn't caught up to your accomplishments. But I used to think that going out and saying who I was and being confident about that was bragging. And now I know better because when I stand up and talk about who I am and what I can bring to the table, I open up opportunities to serve people.
And so I want people to know on this podcast that there are people out there waiting for you right now. And they're waiting for something that nobody else but you can give them. And so when you stand up, when you believe in that, when you use your voice, when you know that who you are is more than enough, you open up an opportunity to serve the people who are waiting for you.
And if you're listening to this and you're getting any value from it at all, know the only reason you're hearing me is that I took the leap a number of years ago and I wrote a book proposal in which I said, Alex Carter is the world's leading negotiation trainer to the United Nations, Fortune 500 companies and organizations around the world.
And I cringed as I wrote it, but I did write it and I put it in there. And now as a result, we're speaking together. So get out there. Don't make people wait any longer and serve the folks who are waiting for you.
Wow, that was powerful. Alex, everybody listening, first of all, I hope you enjoyed it. Let us know. And I want you to shine your light. I want you to find that voice. Somebody in the world needs to hear it. So let's go get it. I love that, Alex. Thank you for the brilliant conversation. Thank you for having me. I hope you enjoyed this as much as I did. If you did, please share it with friends.
Now, also, if you're feeling stuck or simply want more from your own career, watch this 30-minute free training at leapacademy.com slash training. That's leapacademy.com slash training. See you in the next episode of the Leap Academy with Ilana Golan Show.
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