From Agreeable to Assertive: How to Stop Losing Yourself in Client Relationships | EP 48

You've said yes when every part of you wanted to say no. You've softened your feedback until it barely meant anything, just to avoid making someone uncomfortable. You've held back your real opinion in a client conversation, a team meeting, a collaboration — not because you didn't have one, but because you were afraid it would cost you the relationship. If any of that sounds familiar, this episode is for you.

At its root, people pleasing is more of a survival strategy than a character flaw. And for a lot of you, it's worked. Maybe it kept the peace in a household that needed keeping. Maybe it helped you navigate school or a toxic workplace where your safety depended on being agreeable. Maybe it's the thing that made you good at your job — attuned to what people needed, flexible, easy to work with.

In psychology and trauma research, there's actually a name for this pattern: the fawn response, coined by therapist Pete Walker. It's considered the fourth stress response alongside fight, flight, and freeze and what makes it different is that it doesn't look like fear. It looks like helpfulness. It looks like warmth. It looks like being the best team player, which is exactly why it's so hard to recognize and so hard to change. Research on people pleasing in driven, high-achieving women has found that fawning frequently coexists with professional success meaning you can be capable and accomplished at work and still lose access to your own voice the moment a relationship feels even slightly risky. 

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What to listen for in this episode:

• Why people pleasing isn't a character flaw but a nervous-system survival pattern and why understanding it intellectually isn't enough to change it
• The hidden costs of chronic accommodation: resentment, lost identity, and burnout that shows up in your energy, creativity, and decision-making
• Specific, practical phrases for replacing over-agreement with honest, assertive communication that actually strengthens client trust

If you've been performing a version of yourself to keep everyone else comfortable, ask yourself: what would it cost you to keep doing that for another year — and what might it cost you to stop?

Transcript

You're listening to Entrepreneur Encounter, the podcast where soft skills meet real talk for creative business owners who are building with purpose. I'm Dana, a Pinterest marketing strategist and agency owner helping wedding pros and creative entrepreneurs get seen without burning out. And I'm Sarah, a business and team strategist who helps small teams and podcasters communicate clearly, lead with empathy, and grow sustainably. Together we're unpacking the messy, meaningful side of entrepreneurship.

From boundaries to burnout, leadership to listening, so you can build a business that actually fits your life.

Hey, welcome back to the Entrepreneur Encounter. I'm Dana, part of the duo, and today you have just me flying solo because Sarah is dealing with some internet issues, and we all know how work from home stressful that can be. So she'll be back next week. But honestly, this topic felt a little like one I needed to sit with on my own anyway, because it's personal and I think it might be personal for you too.

So here's the question I want to open with this week. Have you ever said yes when every part of you wanted to say no? Have you ever softened your feedback until it meant almost nothing just to avoid making someone uncomfortable? Have you ever held back your real opinion in a client conversation, a team meeting, a collaboration simply because you were afraid that saying what you actually thought would cost you that relationship?

cost you that relationship. I'm gonna raise my hand on that one because that's true. that's definitely something that I've done. And if any of that hit close to home for you, this episode is for you and I hope you stay tuned through the entire thing. We're talking today about people pleasing, what it actually is, where it comes from, what it's quietly costing you in your business and your relationships.

And most importantly, how to start showing up more fully without blowing everything up in the process. But before we dive in, I want to mention something quickly. If you've been feeling unclear about your direction in your business, I know sometimes the summer can create a whole lot of chaos. So you know you want to make changes, but you're not sure where to start because you are balancing so much during the season. Sarah and I put together a free resource called the 20 Minute Clarity Map. It's a simple guided tool to help you get.

Clear on what you actually want and what's getting in the way. As always, there is no fluff, there is no overwhelm in this process. You can grab it at the link in the show notes. All right, so let's get back to the topic at hand and start with something that I think is really important to stay, and that is people pleasing is not a character flaw. I know sometimes it seems like it's such a negative thing.


You know, it does get in the way. It's not a weakness. It's not a bad thing to have empathy and want to help people. It's not proof that you're too nice or too soft or somehow not cut out for leadership. I hope you heard that last one. But people pleasing at its root is genuinely more of a survival strategy. And for a lot of us, it's worked. Maybe it kept the peace in a household that needed keeping. Maybe it helped you navigate school or a

Toxic workplace environment where your safety depended on being agreeable. Maybe it was the thing that made you good at your job. You were attuned to what people needed, you were flexible, you made things easier for everyone around you. In psychology and trauma research, there's actually a name for this pattern, and it's called the fawn response, coined by therapist Pete Walker. It's considered the fourth stress response alongside fight, flight, and freeze.

And what makes it different from the others is that it doesn't look like fear. It actually looks like helpfulness. It looks like warmth. It looks like being the best team player, which is exactly why it's so hard to recognize and so hard to change if you are someone like myself, a genuine people pleaser. And here's the part that really lands for me personally is research on people pleasing patterns in driven.

High achieving women found that fawning frequently operates alongside professional success, meaning you can be incredibly capable at work and still completely lose access to your own voice the moment a relationship dynamic feels even slightly risky. Those two things coexist more than we'd like to admit. So if you've ever thought, I know better, but why do I keep doing this? That's probably why. It's not a knowledge problem.

It's a nervous system pattern. And nervous system patterns don't change just because you understand them intellectually. They change through practice, small baby steps, through repetition, through slowly building the evidence that it is safe to say what you mean and not hide your voice. The real issue usually isn't that you care too much about other people. It's that at some point your needs and other people's comfort got tangled together.


And somehow in that tangle, your voice got a lot quieter. This episode is about finding that again. So here's a question I want you to hold as we go through this episode a little bit more. Is there a place in your business or even your personal life where you're consistently shrinking to keep someone else comfortable? Not a rhetorical question. This is an actual question. And we're going to come back to it later in the episode. But for now, I want to talk about the cost of this.

Concept for a moment. Because I think this is where people pleasing stops feeling like a personality quirk and starts feeling urgent, and you need to change it. There are those obvious costs you take on work you don't want. You say yes to a scope that stretches you way too thin. You discount your prices because someone pushed back and the discomfort was too much to sit with. Those are real and they do matter. I'm

Fairly confident I'm guilty with all of those in the last six years that I've owned my own business. But there are quieter costs that I think hit harder in the long run, and I've had to learn to recognize them. And one of them is resentment. And I want to be honest about this. I have felt it in more ways than one. You say yes when you mean no often enough, and someone starts to calcify. You don't feel generous anymore.

You feel drained, you feel like you're doing everything for everyone, and nobody is doing anything for you. And the hard truth is nobody knew you were struggling because you never said so. And that's been a big eye opener for me in the last couple of years, honestly. Psychology Today describes people pleasers as often experiencing what they call a lost identity. When you spent so long shaping yourself around what other people need.

You genuinely lose track of what you want or even what your basic needs are. And that's not a small thing in a business context because your business is supposed to be an expression of who you are and the things that you value deep to your core. And if you don't know what you value, that clarity is gonna disappear and it will domino affect every other area of your business. There's also a burnout piece here that I can't skip over.


Research from 2024 and 2025 found that employees who feel they can be more authentic selves at work are two and a half times less likely to feel emotionally drained. Two and a half times. That's not a small margin. And when you're a solopreneur or in that early stage entrepreneurship who is constantly performing a version of yourself that keeps everyone else comfortable, that emotional drain is going to show up somewhere, probably in more places.

It's gonna be in your energy. It's gonna show up in your creativity, your client relationships, your ability to make clear decisions. And here's the part that feels most counterintuitive. People pleasing doesn't actually protect your relationships the way you think it does. Research on assertiveness and relationship satisfaction consistently shows that when you withhold your real thoughts and needs, even with the best intentions, it creates some sort of distance.

Between you and the other person. It's not connection. The person in front of you is getting a performed version of you, not the real one. And a performed version, however polished you may think it is, cannot be genuinely close to anyone. I had a client relationship a few years ago where I kept softening my recommendations. They pushed back on a Pinterest strategy decision or a website gallery or blog post. And I'd back down even when I knew I was right.

And what happened over time was that they stopped trusting my expertise because I kept second guessing it in front of them. That relationship I was trying to protect actually eroded because I was too afraid to hold my ground and I didn't let the data speak for itself. The moment I started saying, I hear your concern, and here's why I'm still recommending this, everything shifted. That my clients learned to trust me more and not less. So the reflection question here is think about a relationship in your business.

A client, a collaborator, someone on your team, where you've held back or have been holding back for a while. And what's the thing you haven't said yet to them? And what is it costing you to continuously not say it? Here's the thing that I I think stops a lot of people pleasers from changing their patterns. And it's that they've seen what the other end of the spectrum looks like. They've been around people who are blunt to the point of being unkind.

Who say, I'm just being honest, right before they say something that lands like a weapon, and they think if I stop being the person who keeps the peace, I'm gonna become that, and I don't wanna be that. But that is false binary. There's a whole spectrum between shrinking yourself to keep everyone comfortable and bulldozing people with your needs. And the middle of that spectrum has a name and it's called assertiveness. Psychology Today describes assertiveness.

As that golden middle ground of communication between the person who explodes and the person who says nothing at all. It's expressing your real thoughts, feelings, and needs in a way that's direct and honest, but also respectful of the person that you're talking to. There is that happy middle ground. It takes work, it takes practice, but it does exist and you can accomplish it. It doesn't require an apology.

And it doesn't require any sort of justification. It just requires clarity on your part as well as the others. And here's what research on relationships and assertiveness consistently tells us. Assertive communication, meaning saying what you actually mean in a clear, kind manner, does not damage relationships. Withholding communication does. One study found a significant relationship between assertiveness.

And both mental health and relationship quality, meaning the more able you are to say or state what you need, the healthier relationship becomes. Not weaker, stronger. And that's a really important thing to remember, even when it's uncomfortable or feels scary to share your opinion. So, what does assertive communication actually look like and sound like in real life practice?

Let me give you a few concrete examples because I find that people please often know what they want to speak up on. They just don't know how to start. You've probably replayed it a ton of times in your head. It's just about opening your mouth to actually do it. So instead of, sure, I can do that when you can't, try saying something along the lines of that timeline doesn't work for me. Here's what I can commit to instead.


Instead of over-softening feedback until it disappears, try stating, I want to be honest with you because I think it'll help. Here's what I'm seeing and here's what I suggest. That's letting the data speak for you. That is non-emotional feedback, 100%. Instead of agreeing with a client's direction when you know it's wrong, try saying, I hear where you're coming from and I want to share a concern before we move forward.

Notice what these phrases all have in common. They're not soft, but they're not sharp either. They're clear, they're, you know, empathetic. They name what's true without editorializing it. They leave room for the other person to respond. And that's what assertiveness is. Not a performance of confidence, but the practice of saying what's real in a way that keeps the relationship intact. Both parties are heard, both parties have clear communication.

So the reflection question for this segment here is: Is there a conversation you've been avoiding with a client, a collaborator, a team member because you're not sure how to have it without it going badly? What would you say if you trusted the relationship could handle the honesty? And I'm gonna point out here: if the relationship cannot handle the honesty, it's probably best for you to part ways anyway. But take it as you will. So

We've talked about what people pleasing is and where it comes from. We've talked about what it can cost you. We've looked at the difference between assertive and aggressive communication. Now let's talk about what to actually do because this is where it gets practical. And this is usually my favorite part of any episode that we record: the practical ways to implement it in your life. So the first thing I want to say is you don't have to start big. In fact, I'd

Actively recommend that you not start big and start small. If you've been quietly agreeing for years, trying to suddenly draw a hard line with your most important client is probably going to feel terrifying and it's probably going to go poorly, not because assordiness doesn't work, but because the muscle isn't built yet. Think of it the way that you'd think about any other skill. You don't run a marathon before you can run a mile.


You practice in low stakes situations first. You share your real opinion about where to eat lunch. Maybe you push back gently on a deadline that doesn't work. You tell a collaborator what you actually need from them on a project. You don't jump through hoops to get all the information without their help, basically. These are all small moments, repeated. And over time, they build the evidence in your nervous system that speaking up does not end relationships. It deepens them.

There's a framework that therapists use for this that I love, and it's called name it to tame it. I wish I had come up with that myself, but I didn't. The idea is that before you can change a pattern, you have to get good at noticing it in real time because that's half the battle. If you don't recognize it, you don't see anything to change. So the practice is when you feel the pull to shrink back, when the yes is forming before you've even thought it through.

Name it internally. This is my people pleasing response. Or this is my Beth response. This is my Elizabeth response. This is my name it. That tiny moment of naming gives you a beat of a choice. And a beat of choice is all you need to do something completely different and to maintain those boundaries and speak with assertiveness and not aggressiveness. The second thing I want to offer is.

Is what I call the honest and kind reframe. Because I think a lot of people pleasers believe at some level the honest and kind are opposites, or that honest and kindness are opposites. That if you're being fully honest, you're probably being at least a little unkind. And if you're being kind, you'll probably have to hold something back. So you're holding back honesty. But I promise that's not true.

Honesty is one of the kindest things that you can offer someone. When you soften your feedback until it means nothing, you're not protecting them. You're depriving them of information that they could use, not only in their relationship with you, but in their relationship with others. When you say yes to something that you can't deliver well on, you're not being helpful. You're setting both of you up for a mediocre outcome or you into a straight one-way lane and overwhelm and exhaustion and


It's hard to come back from that. So honesty and kindness are not opposites. Honest and harsh are opposites. You can be honest and kind at the same time, and it does take practice, but it is learnable. And I highly recommend you start learning how to do that if that is something that is concerning you. So your action item or action homework this week is to identify one conversation you've been avoiding.

or one pattern that you've been repeating, saying yes to when you mean no, softening feedback into silence, agreeing when you would actually disagree. Just one. Like I said, we're starting small. And this week practice showing up differently in that one small place. It doesn't have to be perfect. We aren't striving for perfection. We're striving for discipline. We're striving for progress. Just more honesty than the last time. And then notice what happens.

Notice that the relationship likely doesn't end. And notice that you feel a little lighter afterwards. That's the data that your nervous system is needing so that you can continue to grow this skill. And if you want some structured support, getting clear on what you actually want, including in your business relationships and your direction, I want to mention the 20-minute clarity map again. Sarah and I designed it specifically for moments like this one.

When you know something needs to shift, but you're not sure where to start. It's free, it's quick, and again, it's linked in the show notes for you. So let me land this somewhere super simple. People pleasing is not who you are. It's something that you learned to do because at some point it kept you safe. And it probably made you really good at reading the rooms and taking care of the people around you and smoothing things over.

Those are real skills. They're valuable skills and they have genuinely helped you along the way. But there does come a point, and I think a lot of you listening are at that point or approaching it, myself included, where the cost of staying quiet becomes higher than the discomfort of speaking up. Where the relationships you're protecting by holding back would actually be stronger if you brought more of yourself into them. Where your business would be.


Clearer and your leadership would be more trusted if you stopped performing agreeableness and started practicing honesty. You can be honest and still be kind. You can hold your ground and still keep the relationship going strong. You can show up fully and still be someone people want to work with. In fact, I would argue you become that person, not despite of your honesty, but because of your honesty.

Some more people want to work with you because they know what to expect and they know what you're going to share is important and worth sharing. That's the work. It's not dramatic. It doesn't happen all at once. It's one conversation at a time. We love having one conversation at a time. It's one moment of choosing your voice over your discomfort. And it accumulates into something that feels eventually a lot more like freedom than people pleasing ever did.

If this episode gave you something to think about, I'd love for you to share it with another entrepreneur in your life who might need to hear it and end their people-pleasing ways. And if you're ready to get clear on what you actually want in your business, your leadership, your direction, that 20-minute clarity map is waiting for you in the show notes and it's a great first step. Sarah will be back with me next week. Until then, speak up a little more this week. Start small.

And just notice what happens. I promise, the world does not end and it's usually a little bit better when you do. See you next week. You can now follow us on LinkedIn at Entrepreneur Encounter.

Thanks for spending time with us today. If something in this episode gave you a fresh perspective, share it with a friend or send us a DM. We love hearing how these conversations land with you. And if you're curious about how soft skills can support your next season of growth, we each have more resources to share. You can find Dana on Instagram at Dana's.desk.nc for pinch a strategy and intentional marketing. And Sarah.

at You Are Rembert for team development, business leadership, and podcast support. Until next time, keep leading with purpose and growing with intention.