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Working Hard with Grace Beverley

27 Oct 2025 · 16m

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How to Ask for What You Want (and Actually Get It) Without Feeling Like A Bitch

In short

In this episode of Working Hard, host Grace Beverley discusses the challenges many people, particularly women, face when it comes to asking for what they want. The episode features insights from guest Terri Cole, a boundary expert and author of Boundary Boss, who helps unpack the psychology behind assertiveness and effective communication.

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0:11What is up? I'm Grace Beverley and welcome back to Working Hard. the podcast shape guidebook on how to improve your own life and achieve what you actually dreamed of doing, because life's too short for boring podcasts and bad advice.

0:25What is up and welcome back to Working Hard. Today we are talking all about asking for what you want and more importantly, how to do it without feeling shame or feeling like a bitch. It sounds very simple, but in practice, I just don't think it is. Maybe it's asking for a raise, maybe it's pitching your work, maybe it's setting a boundary or even just saying no. And then that little voice kicks in. Will I sound rude? Will I come across as difficult? Am I being ungrateful? And here's the thing. That voice isn't just in your head. It is cultural. Female assertiveness has had a terrible PR problem for centuries.

0:57We're taught from the moment we're little girls to be agreeable, polite and accommodating. To be good girls and to put other people's comfort before our own. And I feel like while being kind and accommodating can absolutely be real strengths and are definitely strengths I like to develop over time, they also can become shackles when they stop us from advocating for ourselves. Because let's be honest, what is seen as leadership in a man is often seen as bossy in a woman. A man setting boundaries is respected and a woman setting the exact same boundary is labelled difficult. Research backs this up again and again, unfortunately, but honestly, most of us also don't need the stats because we've lived it.

1:30I wanted this episode then to be about reclaiming assertiveness from that narrative, about making directness feel powerful but not pushy, and learning how to ask for what you want clearly, confidently, and without the guilty aftertaste. Because asking for what you need is not rude or selfish, and our lack of being able to do so is quite frankly holding us back. But before we get into it, you know what I'm about to say. I looked at our stats this morning and it said that only 24 % of people who listen to this podcast every week actually follow us on their podcast app, which is an absolute tragedy and a drama because we all love habit stacking over here and hitting that button saves you so much time searching through all the podcast bros to find us on a Monday morning.

2:05And also not gonna lie, it helps us a lot too. Each follower means we can get bigger and bigger guests, spend more time on the podcast, really invest into all of the episodes. So I feel like it's a win-win.

2:21We have all very much been there. You're writing an email asking for clarity on a deadline or putting in a request for a pay rise and suddenly your message turns into an essay. You add just or sorry five times. You soften it with if that's okay or if that makes sense. You reread it a dozen times and you still feel like you're asking too much. We've been conditioned to see confidence as arrogance, directness as bitchiness and strength as being too much. The cost of that conditioning Every time you don't ask for what you need, you send a message to yourself that your needs don't matter. That is not the energy that we're bringing into our careers, our relationships, or our personal growth anymore.

2:57So let's get into the data on how we can actually stop this. It's not just anecdotal data. The research is pretty clear. A Harvard Business Review study in 2019 found that women who were assertive in the workplace were 25 % more likely to be described as abrasive compared to men showing the exact same behavior. That is the likability penalty in action. There is also proof that assertiveness is directly linked to better outcomes. A 2021 meta-analysis in the Journal of Applied Psychology found that people who assertively advocate for themselves are more likely to get promoted, receive raises, and feel more satisfied in their job regardless of their gender.

3:33And there's also fascinating research from Stanford that shows women tend to undervalue themselves in negotiations, often asking for 20 to 30 percent less than men for the exact same work, which means in very real terms that not asking is costing us a lot both individually and as a collective. So why does asking for what you want feel so difficult? Psychologists talk about assertiveness as existing on a spectrum. On one end you have passivity, staying quiet, saying yes when you mean no, putting others needs above your own. On the other you have aggression, pushing your needs in a way that disregards others.

4:04Assertiveness sits in the middle, it's about expressing your needs and boundaries clearly. It's not about being louder, it's about being clearer. but then there's social conditioning layered on top. Sheryl Sandberg popularized the idea of the likability bias in Lean In, that women are expected to be warm, communal, agreeable. When you break that script by being direct, you're often penalized socially. You're bossy, you're cold, you're too much. Add that to a lifetime of people-pleasing and being taught that whatever makes as few as people uncomfortable around you is right, or if you were praised as a child for being easygoing, chill, adaptable, or overly empathetic, you've probably internalized the idea that your needs matter less than everyone else's.

4:41So of course it feels uncomfortable to suddenly say, actually, I need this. And finally, there's also the psychology. A phenomenon called cognitive appraisal shows that how we frame a behavior changes how we feel about it. So if you see assertiveness as rude, you'll avoid it. Whereas if you reframe it as honesty and self-respect and helpful clarity, it suddenly feels less like a confrontation and more like an act of integrity. So how do we actually go about putting this into practice? We'll get into that right after the break. So here are my six steps for practicing how to ask for what you want.

5:13Step one, audit your language. Open your last five emails or Slack messages and highlight every just sorry if it's not too much trouble or if that makes sense. These are micro apologies that shrink your authority. Rewrite one of those emails without the disclaimers and notice how much clearer it sounds. Then challenge yourself to send your next message without any of those filler words. Step two, swap to I statements. Practice rephrasing common phrases. Instead of you didn't make this clear, say I need more clarity on this deadline. Instead of sorry I can't, say I'm not available for that. Write down three situations where you know you'll need to assert yourself this week and script I versions in advance.

5:54Step three, give yourself permission. This is so important. Before you ask for something, take a breath and literally tell yourself, this is not rude, this is honest, or clarity is kindness. Say it out loud if you can. Over time, this trains your brain to unlink assertiveness from meanness. It's literally practicing the cognitive appraisal we discussed earlier. Step four, practice the short stop. Next time you set a boundary, resist the urge to justify it with an essay. Try, I won't be able to make that, full stop. Or if the silence feels uncomfortable, just let it be uncomfortable. This is one of the biggest tactics that I've learned for so many different things.

6:29Once you've said what you want to say, you can be silent. It is fine. You do not need to fill in the gaps and that is tough from a yapper like me. But the goal here is to build tolerance for not padding your no with endless explanations. Step five, anchor it to your why. Before you make an ask, think about the bigger reason behind it. Are you asking for this raise so you can build financial security? Are you asking for it because it reflects your job role? Are you saying no to this project to protect time for deep work? It's very motivating when you know why you're making yourself feel uncomfortable to stick to exactly what you are saying because you know why you are asking for it.

7:00As always in these episodes, I always want to speak to an expert on these things. So today I spoke to Terry Cole. She is author of Boundary Boss. I really wanted her to be able to help us unpack why we find it so hard to ask for what we want. We were all sort of indoctrinated into the cult of nice, right? What are the messages that we heard? Where's my happy girl, turn that frown around. If you don't have anything nice to say, don't say anything at all. From early on in life, we were literally trained to be self-abandoning. I like to say we were raised and praised for being self-abandoning codependents.

7:36And this was a socially sanctioned experience, right? The more self-abandoning, the better, according to society when you come to being a woman. And so I think that we were really set up to fail. And that's also why there's so many myths around having good boundaries, right? That, oh, to have good boundaries, I need to be mean, I need to be bitchy, I need to be self-centered. It's so like unfeminine, quote unquote. And why is that? I mean, reality is it's from the patriarchy and the way that we were raised. And then you get into relationships and there's that same expectation that, you know, we should endlessly be thinking about other people.

8:16If we're real women, then we are last on our own list. So I just want people to think about their boundaries as their own personal rules of engagement. This is how we let other people know what's okay with us and what is not okay with us, right? So let's just simplify it. They're made up of your preferences, your limits, and your deal breakers. So that's what boundaries are. Why is it difficult to ask for what you want? because we were trained not to. We were trained to focus on other people. And I think that we really have to look at what the cost is for not asking for what we want or for not being honest.

8:55It's not just asking, it's negotiating for our needs, right? And what happens when we don't? When you think about being compliant, what does that mean? That means a lot of times it means saying yes when you'd really rather say no, because you don't want to be perceived as being rude or not nice. So when we really break that down, what are we doing? When you say yes, when you want to say no, you are actually giving the people in your life corrupted data about who you are. They don't know you when you are not telling the truth. And then you are in relationships for decades with an existential loneliness because literally nobody knows who you are because you're just going along to get along because you are saying yes when you want to say no.

9:41So it is incredibly important that you become fluent in the language of boundaries and you absolutely can because you're so worth knowing. Number one, we're going to take a quick resentment inventory because this is going to be like a GPS to show us where either boundaries need to be established, boundaries need to be reinforced, or somehow a need is not getting met for you if you are feeling resentful in relationships. So you're just going to do a list. Who are you holding sort of resentment towards right now in your life and why? So we'll have listeners, They can write out. And then we look at that list and go, okay, so what is my 50 % of this experience?

10:32Right? Am I not speaking up? Because so much of the time, it's that we are upset about something, have our feelings hurt about something, feel snubbed by someone or not considered by someone, but we don't say anything. So we're not even giving them a chance to be better or to step up for us because they don't know. And it's like, people can't read our minds. So the first thing you're going to do is take a resentment inventory and decide what actions do you need to take to get rid of some of that resentment. So that's number one. And the second thing people can do is they can learn to stop the auto yes, right?

11:16If you were a very sort of people-pleasing type person. And I have to say many, many, many of us are. I'm a recovering people pleaser. And that's really what hopefully my books are helping people do. And my courses and my mastermind is to be former people pleasers. But when you think about what is a people pleaser means, we're prioritizing what you want over what I want. So there's like this inherent self-abandonment. And so for, you know, if you want to get into recovery, you want to stop the auto yes, which means that you learn how to buy time. So when someone asks you to do something, a lot of times someone will ask you to do something and you know from the second they ask it, you do not want to do it.

12:01You have no intention of doing it. But if you're a people pleaser, you may say yes. So all I'm saying is how about learn to say, oh, hey, I need to check with my partner or with my sister or let me check my calendar and I'll get back to you. Thanks for thinking about me. We learn how to buy time instead of just appeasing or giving an auto yes, because it makes it so much easier to come back and give an honest no when you haven't already given a reactive yes. let's just say you're in the corporate world, right? It makes a difference if you are trying to set a boundary with someone where there's a power in difference.

12:45So the way you would set a boundary with a boss would be different than the way you would set a boundary with a coworker, which would be different than the way you would set a boundary with a subordinate. Because if someone has the power to fire you, right, you have to look and go, what is in my description? What is required of me for this job? Do I have a right to set this boundary? And a lot of times you do, and then you have to figure out what is the best way to actually do it. If you're on the fence about asserting yourself, because a lot of women don't ask for raises or don't ask for the amount of money that they know they're worth.

13:20They know someone else doing a similar job or not even doing the job as well as they are, is making more money. And again, we've been taught that it's like gauche to talk about money. I mean, think about what are the money, the limiting money stories that you may have. So that impacts your ability to do it. But you also have to look at it from the point of view that taking care of yourself, right? What you think, what you want, and how you feel has to matter. And it has to matter to you more than what anyone else wants, thinks, or feels in this life. And that means learning how to have a difficult conversation, right?

14:04Learning how to assert yourself. You can say, I'd like to make a simple request, right? There's ways that you can approach this, but we have to go in before we go out. Meaning you have to understand what you learned, what your downloaded boundary blueprint is all about, meaning you learned it in your childhood home, the country, the culture that you grew up in. All of those things come together and they unconsciously impact how we approach setting boundaries. But the greatest thing about this is that it is a skill. You can learn. It's just like learning a language. You wouldn't expect to be fluent in Russian simply because you really want it to be, you would know, I need a teacher.

14:49I need to learn. I need to understand. So this is sort of the same thing. The last thing I want to say is the reason why boundaries are so important is because if we are not studying boundaries and asserting the truth about how we feel, even if it's just your preferences, what ends up happening is that people don't know you. And so how can anyone authentically love you, if no one ever really authentically knows you. And I just want to leave anyone listening with the thought that you are not optional. Like you as a person are essential in this life and in this world. And you have something unique to bring and to share, but you will never do it if you stay having disordered boundaries as a people pleaser.

15:38You won't because it takes boldness to do it. But I just want to leave you with the thought that we need you and you are so worth knowing. Terry's so great. I would really recommend getting her book if you're wanting to do some further reading on this. So that is your crash course in asking for what you want without feeling like a bitch. If you want to learn more, subscribe to the Working Hard newsletter. I'll be sharing my further reading recommendations on there the day after release and it's packed with loads of other great things as well. Thank you so much for listening and I will see you next week.

16:09Thank you.

From the publisher

This week’s episode is for anyone who struggles to speak up the people who overthink every ask, soften every sentence, or apologise before they’ve even said anything.


It unpacks why asking for what you want feels so uncomfortable (especially for women), the psychology behind it, and how to start doing it without guilt.


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A huge thank you to the wonderful Terri Cole for speaking to me for this episode!


Read Boundary Boss here: https://boundarybossbook.com/

Terri's free boundary quiz: https://boundaryquiz.com/

Her Instagram: https://www.instagram.com/terricole/


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