Saying Yes Too Often? Here’s How to Set Boundaries | Amplify Podcast

Written by Lauren | Jul 8, 2025 8:00:00 AM

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Kwame shares a deeply personal and formative childhood story that shaped his journey from people-pleaser to negotiation expert, revealing how his early experiences led him to compromise himself for the sake of being liked. He explains how this common “people-pleasing pressure” can actually damage the very relationships we’re trying to protect.

Let this episode be your permission to stop shrinking and start being clear.

YOU’LL DISCOVER:

[dsm_icon_list list_vertical_alignment=”flex-start” list_space_between=”16px” _builder_version=”4.27.4″ _module_preset=”default” text_font=”|600|||||||” text_font_size=”18px” text_line_height=”1.5em” custom_padding=”10px|1%|45px|1%|false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][dsm_icon_list_child text=”The surprising link between childhood experiences and our adult people-pleasing tendencies.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”How the %22big five personality traits%22 (openness to experience, conscientiousness, extroversion, agreeableness, and emotional stability) influence our negotiation style.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”Why being overly agreeable can lead to an %22emotional hangover%22 and resentment.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”The profound impact of unspoken boundaries on relationships, both personal and professional.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”Kwame’s simple %22yes-no-yes%22 framework for setting and maintaining effective boundaries.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”Why the definition of negotiation is often warped, and how redefining it can empower you in daily life.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”The concept that %22assertiveness is teaching the person how to treat you.%22″ font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”How to navigate the %22assertiveness penalty%22 that women (and other groups) often face in professional settings.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”Why overthinking is your %22kryptonite,%22 and how a %22shot clock%22 can help you make better decisions faster.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”The psychological insight that you’ll never truly %22get over%22 stage fright, and why that’s a good thing.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”How Kwame uses AI daily to amplify his humanity, manage emotions, identify blind spots, and create cohesive negotiation strategies.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][dsm_icon_list_child text=”The power of mirror neurons and how our tone and attitude can unconsciously impact others.” font_icon=”N||divi||400″ icon_color=”#E09466″ icon_font_size=”18px” _builder_version=”4.27.4″ _module_preset=”default” custom_padding=”||||false|false” hover_enabled=”0″ global_colors_info=”{}” sticky_enabled=”0″][/dsm_icon_list_child][/dsm_icon_list]

FOLLOW KWAME

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ABOUT OUR GUEST

Kwame Christian, Esq., M.A.

Kwame Christian, Esq., M.A. is the CEO of the American Negotiation Institute (ANI) and a leading voice in the field of negotiation. He hosts the #1 negotiation podcast, Negotiate Anything, and his TED Talk has garnered over 600,000 views. He is also a LinkedIn Top Voice and the author of Finding Confidence in Conflict and How to Have Difficult Conversations About Race. Kwame’s mission is to make the world a better place, one difficult conversation at a time.

RESOURCES & LINKS

American Negotiation Institute: americnnegotiationinstitute.com

Follow Kwame Christian on LinkedIn

Listen to the Negotiate Anything podcast

Finding Confidence in Conflict by Kwame Christian

How to Have Difficult Conversations About Race by Kwame Christian

TEDx, Finding Confidence in Conflict

Amplify with Jess is produced by Walk West and brought to you by Mic Drop Workshop.

TRANSCRIPT

Jess [00:00:00]

Hi everyone. Welcome. I am so glad that you’re here joining us live. Hello, Cindy. I’m glad that you need to learn this ’cause I need to learn it too. I’m selfish. I invite guests on that I actually need to learn from myself. Same with Sharon. Hello, Sydney.

Today’s guest is a dear friend of mine, Kwame Christian. He’s someone that I met on stage years ago—I don’t even remember how long it’s been. You know when you first see someone and their thing is negotiation? And even—I’m not gonna lie, Kwame—when you post your gym stuff, I’m like, “This guy kind of looks like a hardass.”

But when you meet him, which you all are about to, you realize—oh, he is one of the kindest, most genuine people I’ve ever met. Which makes me believe that in order to be a great negotiator, it doesn’t mean that we have to alter ourselves or put on our boxing gloves. It’s actually more about intuition and listening.

Kwame’s gonna tell us a lot more, but I just want you to know my first impression was like, “Oh, negotiation?” And he’s completely proven that narrative wrong. He is the CEO of the American Negotiation Institute. He has a number one podcast called Negotiate Anything, which I have loved being on. His TED Talk has over 600,000 views, and he is a LinkedIn Top Voice.

Kwame, my friend—thank you for being here.

Kwame [00:01:00]

Thank you for having me. I appreciate it. You beat me to the Mississippi story. Mississippi in COVID—that’s where we met.

Jess [00:02:00]

And I actually have to say, you gifted me when we had Ellie, my firstborn, a gift that at first I was like, what is he doing? And then I was like, I now repurpose this gift for people that I know having kids. You wanna share what it is? I won’t take the credit.

Kwame [00:03:00]

Yes. Every time I send this gift to people, they’re just like, what? It is almost insulting at first. And then the baby comes and they’re like, oh yeah.

So I send a book, What to Do with an Idea. It’s a great book that I cannot read without crying. I cry every single time I read it. And then the other gift is a set of earplugs—like 50 earplugs. I remember one of my friends said, “What, you don’t want me to hear the cries of my child?”

Jess

Thank you so much.

Kwame

No, you can still hear. It’s just not the blood-curdling, piercing cries of your child. That’s what the earplugs do.

Jess [00:04:00]

Kwame, like I was saying—which I’m sure you were like, “I didn’t come on here to be called a hardass and soft in the same introduction”—but I would love to know what got you started in becoming this negotiation expert. Let’s start there. Then I have a lot of questions about people-pleasing and becoming a confident negotiator.

Kwame [00:05:00]

Great place to start, Jess, because I forget that most people are introduced to me now after the evolution, so they don’t know the full story.

I was actually presenting to a client, LinkedIn, the other day and they said, “Were you always like this, this confident? Or were you that kid on the playground that everybody liked?” And I asked, “Is this a plant?” Because this is where it all started.

So for me, I’m a first-generation Caribbean American. We grew up in Tiffin, Ohio. And if you’re asking yourself, “Where’s Tiffin?” that’s the point of the story. Not surprisingly, there was not much diversity. My joke was always, there were only four Black people in Tiffin at the time—me, my mom, my dad, and my brother. So we stood out.

I know after years of code-switching, now I can sound American, but I had a really strong Caribbean accent at the time. So we stood out even more. I remember in first grade, there was an incident on the playground. I was six years old and this really shaped my life in ways I didn’t fully understand until I was an adult.

I was going to different groups of kids on the playground just trying to get somebody to play with me. I said, “Hey, can I play with you?” One group said no. I tried another group—no. Another one—no. Then the bell rang.

Jess [00:06:00]

I’m about to cry.

Kwame

Yeah, I did cry. I went into school and talked to my first-grade teacher. She saw me bawling and asked, “What’s wrong?” I said, “Nobody would play with me.”

So at age six, I made the decision: I will never, ever allow myself to feel this way again. I’m going to be everybody’s friend. Everybody’s going to like me. I’m going to figure this out.

So fast forward through middle school, high school—it looked like success. I was the most popular kid in school.

Jess

You figured it out.

Kwame

Yeah, I figured it out. We had a small school. I would literally greet everybody by name, from freshman to senior, going through the hallways. But the thing is, that event made me a people-pleaser.

So I would compromise and sacrifice a lot in ways that people couldn’t see or understand, just to get along and not stand out anymore. Even though I had lots of friends and people liked me, there were many times I didn’t like myself.

I studied psychology to understand the root of that fear—the fear of abandonment and rejection. Once I understood the problem, I asked: how do I get over this?

It wasn’t until I discovered negotiation in law school that I figured it out.

Kwame [00:07:00]

I took a negotiation class and entered a competition. My partner and I ended up winning the competition at our law school. That gave us the opportunity to represent the school in Ottawa, Ontario, in the American Bar Association competition. And we won that too.

I had just learned negotiation weeks before and realized—it’s a skill, not a talent. I could learn it.

So I went down this path to help other people because I realized I wasn’t the only one struggling with this.

For me, the best things in life are on the other side of difficult conversations. I want to make the world a better place—one difficult conversation at a time.

Jess [00:08:00]

Damn. Is this the first time you’ve told that story? You know it—it’s like practiced—but that childhood story reminds me of something too.

I think when we were first on stage together, I wasn’t yet talking about my uncle being Bernie Madoff. Do you even know that?

Kwame

I remember you told me off stage, and I was like, “You need to tell this.”

Jess

I know—it took me a while to get there. But one of the stories I tell now is that I asked him, “How did this all begin? You didn’t just one day decide to commit the biggest fraud in history.”

He told me it started when he was growing up in Brooklyn and kids wouldn’t play with him. So he’d go from door to door with a nickel and pay kids to hang out with him. That was the beginning—realizing he could buy people’s attention.

And it never stopped.

So I think a lot of our early experiences shape this desire to be liked. And it’s not self-centered. It’s survival. Wanting to be liked used to mean access to food, water, shelter.

Now, we’re in this new era—this pandemic of wanting to be liked. Followers, likes, being perceived a certain way.

I think people-pleasing has gotten in the way of us being true to what we need and want.

Does wanting to be liked help in negotiation or hurt you?

Kwame [00:09:00]

It depends. I know that’s a cliche answer, but it really does.

We have to lean into the strengths of people-pleasing. It’s not always a bad thing. Being likable, empathizing, building trust—all of that helps in negotiation.

But we also need to recognize when someone is infringing on our boundaries, taking something they don’t deserve, or trying to take advantage.

From a psychology perspective, I like to use the Big Five personality traits: openness to experience, conscientiousness, extroversion, agreeableness, and emotional stability (formerly called neuroticism).

Agreeableness is a big one. Agreeable people are likable. It’s easy for them to make friends. But they don’t want to do anything that might make someone dislike them—so they compromise too often.

And then you’re left with what I call an “emotional hangover.” The emotion fades, but the decision remains. You regret it. You resent yourself. And often, you start resenting the other person too.

Jess [00:10:00]

You also start to resent that person, you know?

Kwame

Yes, exactly. I call it “people-pleasing pressure.” In the moment, we feel pressure to make the other person happy. We think we’re relieving the pressure by saying yes or giving in.

But really, that pressure just builds in the form of resentment. And it’s not the other person’s fault—they’re advocating for what they want.

They’re doing their job. It’s our job to protect our own interests.

We blame them when we should be taking responsibility for ourselves.

Jess

Yes. My husband and I—he runs operations for Mic Drop Workshop—and we both work with the same business coach. One day we decided to do a joint session to work better together as a couple and as a team.

Because don’t get me wrong, two kids under two and a business together? It’s a lot.

We realized he was trying to please me at work—trying to lighten my load—so he’d say yes to things he didn’t actually want to do. Then he’d end up resenting me for it.

And I could feel this hostility.

Eventually we got to a place where I said, “I’d rather you hold a boundary and be happy about it, and I’ll figure it out—than you say yes, not mean it, and build up resentment.”

So people-pleasing can actually damage the relationship we’re trying to protect.

Is that right?

Kwame [00:11:00]

Yes, absolutely. And here’s a quote I love:

“One often meets their fate on the path they take to avoid it.”

That’s from Kung Fu Panda, believe it or not.

Jess

Please tell me that’s yours.

Kwame

I wish. But it’s true.

People-pleasers make sacrifices to preserve the relationship—but those sacrifices often go unrecognized.

The other person doesn’t even realize you gave something up. And as a people-pleaser, you don’t voice your discomfort. You don’t express your needs.

But you can only be inauthentic for so long before it starts to leak out.

Then come the passive-aggressive comments, the tension. And suddenly the relationship suffers.

So one of the best things we can do is set and maintain boundaries and advocate for ourselves. If we don’t, we risk destroying the very relationship we’re trying to protect.

Jess [00:12:00]

So can we get into the tangibles of how to override the people-pleaser in us? How do we set a boundary or negotiate—because sometimes I think negotiation means disagreement. But maybe it’s actually something more positive.

What are some steps we can take?

Kwame

Great question. First, know that the tools for business and personal negotiation are exactly the same. The difference is in tone.

Jess

Did you hear that, honey? It’s not what you said—it’s how you said it.

Kwame

Exactly. We’ll come back to that point.

When it comes to negotiation, we need to redefine it. I define negotiation as anytime you’re in a conversation and someone in that conversation wants something.

That means we’re negotiating all the time. But we don’t label it as negotiation—we call it an argument, a debate, a difficult moment.

So we miss the signal to use our negotiation skills.

Step one is awareness.

Next, when it comes to setting boundaries, I like to use a simple framework: Yes – No – Yes.

The first “yes” is to what I’ve already committed to—the reason I’m saying no.

Then comes a short, firm “no.”

The final “yes” is to the relationship or to continuing the conversation.

So if someone says, “Hey, want to grab lunch on Tuesday at noon?”

I might say:

“Yes, I’ve already committed to lunch with my friend Jess at that time, so I won’t be able to. But I’d love to find another time to connect.”

Short, clear, and kind.

Jess [00:13:00]

And if they keep pushing?

Kwame

If they keep encroaching on the boundary, it’s not your job to entertain it.

You don’t need to diversify your response.

You gave them your reason. That reason doesn’t change.

If they want a different answer, they should stop asking the same question.

Setting the boundary is step one. Maintaining it—and continuing to teach people how to treat you—is what assertiveness really is.

Jess

Oof. Assertiveness is teaching the person how to treat you.

That hits. Especially for women. Because assertiveness gets such a bad rap—it’s called bossy, bitchy, aggressive.

How do we teach people how to treat us… without being seen that way?

Or is it not our problem?

Kwame [00:14:00]

It’s a little bit of both.

We do need to be mindful of tone. But we also need to accept that we can’t control someone else’s perception.

Women face an assertiveness penalty that men don’t—for the exact same behavior.

So we have to be aware of those biases and learn how to navigate them.

I think about bias not as a limitation, but as a strategic consideration.

What are the biases that might be present in this conversation, and how do I move through them?

For example, as a Black man, I face biases too—about intelligence, aggression.

So I’m intentional about my tone, my body language, my presence. I use strategy to help the other person feel more comfortable.

Is that fair? Is it right? I don’t care.

I want to be effective.

Jess [00:15:00]

Is it fair? Is it right? Don’t care. Want to be effective.

I think I need that on a bumper sticker.

And it reminds me of one of your other videos. You said, “The more you think, the more you lose.”

That’s the opposite of how I operate. I do mental gymnastics over every little thing.

Like, I had a speaking gig come in yesterday for next year. It wasn’t even close to my usual fee. And I spiraled.

“How do I let them down gently?”

“Should I negotiate?”

“What if they’re offended?”

Talk to me about how overthinking gets in the way.

Kwame [00:16:00]

If overthinking is your kryptonite, it means you’ve already thought enough.

Overthinkers often just rename their fear. Instead of saying “I’m afraid,” we say “I’m just being thorough” or “I’m being thoughtful.”

But it’s the same loop of thoughts, over and over.

We hit a point of diminishing returns fast.

Unless you’re working on a dissertation or something with huge complexity, most decisions don’t need days of thought.

You already know your numbers. You know your availability. You probably know your answer in the first 60 seconds.

The rest is fear disguised as strategy.

So I use a mental shot clock. Based on the complexity of the decision, I’ll give myself 3 minutes, 10 minutes—whatever makes sense.

Then I run my idea or my message through ChatGPT. I tell it, “Here’s what I want to say. I’m afraid they’ll think this or that. Make this sound clear and kind.”

It gives me a clean version in 15 seconds. I send it. I’m done.

Jess [00:17:00]

So instead of spending a week spiraling over one decision, you just get 32 okay decisions done and move forward.

Kwame

Exactly.

It’s not about making the perfect decision. It’s about building decisiveness. Training your mind and body to operate through fear.

Otherwise, you burn all your energy obsessing over one choice and lose the momentum to make the others.

Jess

This is probably a silly example, but I just got a new car. A minivan.

Suburban mom era, here we are.

And yes, it was a big purchase—I did my research—but then I hit a point where I was like: more thinking won’t change the outcome.

The options are so close. I’m just comparing cupholder sizes at this point.

The cost of overthinking isn’t worth it.

Kwame [00:18:00]

Exactly.

Same thing applies to stage fright, too. And for a lot of your audience—aspiring or active speakers—that fear is very real.

But I always tell people: you’re never going to get over stage fright. And that’s a good thing.

Kwame [00:19:00]

Let me put on my psychology nerd hat for a second.

When we experience fear—like with stage fright—our body responds with a limited set of reactions. Elevated heart rate. Sweating. Stomach fluttering.

But the interesting part is that the exact same physiological response happens when we’re excited.

Like if you see your favorite celebrity across the room.

Heart rate goes up. You sweat. You feel that same tension in your body.

The difference is in how you label it.

So instead of saying, “I’m nervous,” I reframe it. The psychology term for that is cognitive reappraisal.

I tell myself, “It’s game time.”

I listen to music, I let myself feel it, and then I walk on stage. And because I’ve done it so many times, I know I’ll be fine.

The problem is that we feel these sensations, label them as fear, and try to get rid of them.

But the more you resist it, the worse it gets.

If you just accept that this is part of the process—those feelings become energy you can actually use.

Jess [00:20:00]

I remember the song you created with AI for your hype-up playlist. It was brilliant.

And now that we’re talking about AI—I want to circle back to something.

You were such an early adopter.

How are you using AI in negotiation today? Or how can someone listening use it to build confidence?

Kwame

I use AI every day. Literally. Hours every day.

And I study it, too.

I think of it as a self-awareness tool.

I’ll give it different roles depending on what I need. “Be my negotiation coach.” “Be my business partner.” “Be my therapist.”

For example, if I’m upset, I’ll say, “I just need to vent. Don’t fix anything. Just validate me.”

And it works. It’s like having a friend who doesn’t need anything from you.

Once I calm down, I switch roles. “Now be my coach. Tell me what I’m missing. What are my blind spots? What assumptions am I making?”

And every time I do it, I see how human I really am.

Kwame [00:21:00]

It puts me in a better emotional and mental space. I’m calmer. I have clarity. I can build a better strategy.

And most importantly—I can actually execute that strategy.

Because here’s the thing I’ve realized, and I talk about this in my first book, Finding Confidence in Conflict…

In the negotiation world, we’ve been giving people recipes—when they’re too afraid to even walk into the kitchen.

People often know what to say. They just don’t know how to say it when it matters most.

So for me, calming myself down is key. That’s how I avoid getting emotionally charged or slipping into the wrong tone.

Jess [00:22:00]

Yes. And tone matters so much. Especially because women are often told, “Watch your tone,” when they finally speak up.

Kwame

Exactly.

And our tone leaks emotion—even if our words are technically right. That’s because of something called mirror neurons.

These are nerve receptors that mirror the emotions we see in others.

So if someone in the room yawns, you yawn. If someone’s angry, you feel tension.

If I walk into a meeting with a bad attitude—even if I’m saying the right things—my energy shifts the whole room.

So when we’re charged, other people reflect that back.

That’s why I use AI to ground myself before hard conversations.

I want to show up clear. Calm. Focused.

That way, I can advocate for myself and preserve the relationship.

Jess [00:23:00]

Using AI to amplify humanity.

That could be your next TED Talk. It’s so different from the mainstream fear about AI replacing us.

You’re showing how it can actually support our emotional intelligence.

Kwame

Exactly.

It helps you prepare, get honest about your own mindset, and show up with better self-awareness.

Jess

These tips were so good.

There’s a reason you’re the GOAT, Kwame.

For anyone listening—if you want to book Kwame to speak or learn more about his work, visit AmericanNegotiationInstitute.com.

Follow him on LinkedIn. He’s one of my favorite follows and a LinkedIn Top Voice.

Kwame [00:24:00]

Thank you, Jess.

And yes—follow me on LinkedIn, Instagram, wherever you like to hang out.

We also have a free gift for listeners. I’ll send it over to you to share once it’s ready.

Jess

Perfect. We’ll include it when we release the episode.

Also—people in the chat are already ordering your book. Can you share the titles?

Kwame

Yes. My first book is Finding Confidence in Conflict.

The second one is How to Have Difficult Conversations About Race.

Jess

Beautiful.

Kwame, thank you for the earplugs, the book rec, and the wisdom.

Kwame

My pleasure. Thanks for having me.

Jess

And thank you all for listening.

Saying Yes Too Often? Here’s How to Set Boundaries | Amplify Podcast

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