minoanmiss (
minoanmiss) wrote in
agonyaunt2025-10-15 12:31 pm
Entry tags:
Ask a Manager: How Can I Be More Assertive At Work?
A reader writes:
Every since I was a small child I’ve been praised for how nice I am, how likable I am, how good I am with people. In many ways, this is a positive thing. I think of it as a skill that takes effort, but is very useful. However, as I’ve started working professionally I’ve run across a problem. I have a really hard time telling people when they are being awful. I can do normal job-related criticism fine – “please make sure you proofread for typos next time,” etc. – but when it comes to more emotionally turbulent conversations or anything with conflict, I completely freeze up. I have whole conversations ready to go in my head, but I can’t get them out because I know it will hurt people’s feelings and that goes against every fiber of my being, even though I know those people need their feelings to be hurt because they are being awful!
I want to move up in my field, and if I succeed in my goals I’ll end up being responsible for several hundred employees. Logically I know that even if people like me less in the moment, they’ll respect me more in the long run if I can have tough conversations and be firm when necessary, and the people that will resent me are people I don’t want to work with anyway, but how do I convince my mouth and my adrenaline that conflict isn’t something to be avoided?
For example, the last job I worked on, the supervisor directly above me either didn’t remember or didn’t care to know my name and instead called me “baby girl” the entire time. I thought about what to do and decided the next time he said it I would reply, “Actually it’s Jane,” which seemed like a clear shutdown without anyone who heard it being able to accuse me of overreacting as would happen if I said “that’s misogynistic, you asshole, enjoy dying alone with four ex wives who hate you,” which was my internal monologue. But when it happened, I just froze up, and couldn’t do it because my adrenaline started going crazy. How do I stop that or work through it and say what needs to be a said in a confident, non-panicky way without feeling like I’m going to die?
I work in an entry-level job a creative, heavily male-dominated field that is infamous for its sexism and its nepotism. It’s a giant part of the culture to rely on word of mouth, and hire people based on recommendations rather than resumes, so being liked and keeping professional relationships alive is a really important skillset, especially for a woman, but I don’t want to be treated like a doormat and I want to be a leader and it feels like this is holding me back. Any suggestions would be greatly appreciated.
The crux of this is to figure out why calmly asserting yourself feels so rude to you.
It’s definitely true that lots of people have trouble navigating particularly awkward situations, but “hey, please call me Jane” is straightforward enough that the fact your adrenaline is firing so hard makes me think there’s something pretty deeply rooted happening here.
I’m curious about what type of communication you saw modeled in your family when you were growing up — and what lessons you learned about how you should talk to people. Any chance that the parent you identified most closely with wasn’t especially assertive on their own behalf either? Or that you were taught as a kid that things went more smoothly if you didn’t advocate for yourself? Or even that you were outright penalized for asserting yourself?
It might sound like overkill to suggest therapy, but what you’re describing speaks to fundamental ideas about your value and about what you are and aren’t allowed to bring to your interactions with other people. It might be worth digging into some of the underlying beliefs here with a therapist, who can help you figure out where you picked up these beliefs and how you can get rid of them.
But meanwhile — or if that sounds totally off-base to you — there are some concrete things you can do on your own as well.
First and foremost, it’s important to realize that the picture you have in your head of how these conversations will go is probably really different than how they’ll go in reality. Very, very few people are going to blow up if you say “Actually, please call me Jane” or “hey, can you turn your music down while I’m on this call?” Those aren’t inflammatory requests, and they’re not going to sound like attacks or like outrageously presumptuous demands. It might help to think about times you’ve seen other people make similar requests, and really focus on the reaction they received, which was probably not disgusted indignation or hostility. They probably received responses like “sure, sorry about that” or “yes, of course!” — and you will too.
Also, it’s worth thinking about the emotions you’re bringing to the situation. Sometimes when people are reluctant to address a problem, they let it go on for so long that their irritation builds and by the time they do speak up, they’ve become far more frustrated than the situation really warrants. That makes it feel like an even bigger deal in their minds, and they’re more likely to sound confrontational when they finally do say something. But if they’d just addressed it matter-of-factly when the problem first started, it never would have gotten to the point of feeling so adversarial. So speaking up sooner rather than later can actually help these conversations feel less fraught.
And speaking of things feeling adversarial: If you don’t have a lot of experience speaking up for yourself — or good models for how to do it effectively — your internal calibration for tone can be way off. You genuinely might not realize that these conversations can be calm and matter-of-fact, and that can be a huge problem because tone really matters! When you assume it’s going to be a Big Deal to the other person, and when it feels risky and emotionally fraught, or when you’ve let something go on so long that now you’re really pissed off about it, your tone is more likely to be confrontational. That makes the other person more likely to react accordingly … which then of course will reinforce your reluctance to speak up in the future.
But when you genuinely believe that what you’re saying is no big deal — that of course you have the right to ask to be called by the correct name or to ask someone to keep it down while you’re on the phone — your tone is more likely to sound calm, matter-of-fact, and even cheerful. And if it is, the other person is more likely to respond in kind.
If you know someone who gets this right — who calmly speaks up without coming across as a jerk — pay attention to how they do it and what kind of response they get. Plus, by paying attention to their tone, their wording, and their timing, you’ll be able to call on that model in the future when you need it.
One more thing to keep in mind: Most reasonable people actually want to know if they’re doing something that bugs you. Wouldn’t you be mortified if you found out that you’d been inadvertently annoying your coworker for months and she hadn’t told you? Most people would be. So from that perspective, it’s actually a kindness to speak up about this stuff (as long as you do it politely).
And of course, when it comes to people you manage, it’s much more than a kindness: if you avoid those conversations with them, it could end up affecting their performance, their evaluations, their raises, and their professional reputation. Most people want their managers to be up-front with them when those things are at stake.
Ultimately, though, when the potential for even mild conflict is causing this much worry, it’s almost certainly less about the specific conflict at hand and more about something a whole lot bigger. So really do think about therapy, as an investment not only in your career but in your quality of life too.
Update:
I realized, after reading your reply and the comments, that I was letting my self worth get too caught up in feeling like I wasn’t standing up for myself, and then beating myself up for it, which made the stakes feel even higher next time, which made it feel even harder to stand up for myself because it felt symbolic, instead of just a simple but tough work interaction. I decided to strip all that away and identify and attack the problem as systematically as possible.
The problem: People were saying inappropriate and sexist things to me, and I kept getting too anxious to tell them to knock it off.
The solution:
1) Reframe who had the power in these situations. I don’t need to network with these people, I don’t need these people to recommend me for other jobs because I do not want to work with them again. In a way, by being so upfront about their sexism they were giving me the gift of letting me know immediately not to waste my time, and the people who would be missing out on work is them, because I would never recommend them for jobs in the future and would actively discourage hiring them if I was able. Any short term jobs I miss out on now, are well worth it to form a network of people that are actually respectful that I want to keep working with.
2) Give up on ever having that perfect retort that would wither them to their bones, or beautiful speech that would change their life. Instead, I wrote out some very simple, one line, adjustable scripts for every situation I’d come across.
3) Embrace the power of awkward silence. Since I don’t have it in me to make a scene instead just say my one line script, and not say anything else or make it better. Let it be uncomfortable without anyone ever being able to say I was being unprofessional.
4) Practice in lower stakes situations. I did it at a bar, it worked like gangbusters.
5) Go through all my clothes, and pick out all the ones that make me feel as confident as possible, and project the image I want. Only wear those clothes to work, even though it’s just the same ones over and over again.
6) Wait for someone to do something and see how I do.
Results:
Yesterday, an older gentleman went on a long, highly inappropriate ramble and halfway through I interrupted and said, “You don’t need to tell me this, it’s making me uncomfortable.” He was very shocked and offended and just talked and talked and talked about why he wasn’t doing anything wrong, and I said nothing, and I kept saying nothing just staring at him as expressionlessly as possible, until he ran out of reasons why nothing he had done was wrong, and then he actually apologized! I told him I appreciated his apology, and then I left. No one told me not to show up tomorrow, and later on, other people came up to me to talk about it and seemed impressed with how I handled the situation. And actually addressing it in the moment, meant I didn’t have an anxiety about it, because it was all done and over. I felt great! I’m calling this a win.
I could write you a whole essay about how interesting it’s been starting this experiment in simple, practical ways to resist sexism, and then midway through have the whole industry basically implode over the Weinstein case, and everything else that’s come out after. At least for now, people are being more careful which is nice even if it is just out of fear. Hopefully it stays that way.
Also, I got a slight jump in title and pay, and being no longer replaceable in five minutes plus traffic has done wonders for making me feel less anxious at work.
Thank you for you and your commenters’ help!
Every since I was a small child I’ve been praised for how nice I am, how likable I am, how good I am with people. In many ways, this is a positive thing. I think of it as a skill that takes effort, but is very useful. However, as I’ve started working professionally I’ve run across a problem. I have a really hard time telling people when they are being awful. I can do normal job-related criticism fine – “please make sure you proofread for typos next time,” etc. – but when it comes to more emotionally turbulent conversations or anything with conflict, I completely freeze up. I have whole conversations ready to go in my head, but I can’t get them out because I know it will hurt people’s feelings and that goes against every fiber of my being, even though I know those people need their feelings to be hurt because they are being awful!
I want to move up in my field, and if I succeed in my goals I’ll end up being responsible for several hundred employees. Logically I know that even if people like me less in the moment, they’ll respect me more in the long run if I can have tough conversations and be firm when necessary, and the people that will resent me are people I don’t want to work with anyway, but how do I convince my mouth and my adrenaline that conflict isn’t something to be avoided?
For example, the last job I worked on, the supervisor directly above me either didn’t remember or didn’t care to know my name and instead called me “baby girl” the entire time. I thought about what to do and decided the next time he said it I would reply, “Actually it’s Jane,” which seemed like a clear shutdown without anyone who heard it being able to accuse me of overreacting as would happen if I said “that’s misogynistic, you asshole, enjoy dying alone with four ex wives who hate you,” which was my internal monologue. But when it happened, I just froze up, and couldn’t do it because my adrenaline started going crazy. How do I stop that or work through it and say what needs to be a said in a confident, non-panicky way without feeling like I’m going to die?
I work in an entry-level job a creative, heavily male-dominated field that is infamous for its sexism and its nepotism. It’s a giant part of the culture to rely on word of mouth, and hire people based on recommendations rather than resumes, so being liked and keeping professional relationships alive is a really important skillset, especially for a woman, but I don’t want to be treated like a doormat and I want to be a leader and it feels like this is holding me back. Any suggestions would be greatly appreciated.
The crux of this is to figure out why calmly asserting yourself feels so rude to you.
It’s definitely true that lots of people have trouble navigating particularly awkward situations, but “hey, please call me Jane” is straightforward enough that the fact your adrenaline is firing so hard makes me think there’s something pretty deeply rooted happening here.
I’m curious about what type of communication you saw modeled in your family when you were growing up — and what lessons you learned about how you should talk to people. Any chance that the parent you identified most closely with wasn’t especially assertive on their own behalf either? Or that you were taught as a kid that things went more smoothly if you didn’t advocate for yourself? Or even that you were outright penalized for asserting yourself?
It might sound like overkill to suggest therapy, but what you’re describing speaks to fundamental ideas about your value and about what you are and aren’t allowed to bring to your interactions with other people. It might be worth digging into some of the underlying beliefs here with a therapist, who can help you figure out where you picked up these beliefs and how you can get rid of them.
But meanwhile — or if that sounds totally off-base to you — there are some concrete things you can do on your own as well.
First and foremost, it’s important to realize that the picture you have in your head of how these conversations will go is probably really different than how they’ll go in reality. Very, very few people are going to blow up if you say “Actually, please call me Jane” or “hey, can you turn your music down while I’m on this call?” Those aren’t inflammatory requests, and they’re not going to sound like attacks or like outrageously presumptuous demands. It might help to think about times you’ve seen other people make similar requests, and really focus on the reaction they received, which was probably not disgusted indignation or hostility. They probably received responses like “sure, sorry about that” or “yes, of course!” — and you will too.
Also, it’s worth thinking about the emotions you’re bringing to the situation. Sometimes when people are reluctant to address a problem, they let it go on for so long that their irritation builds and by the time they do speak up, they’ve become far more frustrated than the situation really warrants. That makes it feel like an even bigger deal in their minds, and they’re more likely to sound confrontational when they finally do say something. But if they’d just addressed it matter-of-factly when the problem first started, it never would have gotten to the point of feeling so adversarial. So speaking up sooner rather than later can actually help these conversations feel less fraught.
And speaking of things feeling adversarial: If you don’t have a lot of experience speaking up for yourself — or good models for how to do it effectively — your internal calibration for tone can be way off. You genuinely might not realize that these conversations can be calm and matter-of-fact, and that can be a huge problem because tone really matters! When you assume it’s going to be a Big Deal to the other person, and when it feels risky and emotionally fraught, or when you’ve let something go on so long that now you’re really pissed off about it, your tone is more likely to be confrontational. That makes the other person more likely to react accordingly … which then of course will reinforce your reluctance to speak up in the future.
But when you genuinely believe that what you’re saying is no big deal — that of course you have the right to ask to be called by the correct name or to ask someone to keep it down while you’re on the phone — your tone is more likely to sound calm, matter-of-fact, and even cheerful. And if it is, the other person is more likely to respond in kind.
If you know someone who gets this right — who calmly speaks up without coming across as a jerk — pay attention to how they do it and what kind of response they get. Plus, by paying attention to their tone, their wording, and their timing, you’ll be able to call on that model in the future when you need it.
One more thing to keep in mind: Most reasonable people actually want to know if they’re doing something that bugs you. Wouldn’t you be mortified if you found out that you’d been inadvertently annoying your coworker for months and she hadn’t told you? Most people would be. So from that perspective, it’s actually a kindness to speak up about this stuff (as long as you do it politely).
And of course, when it comes to people you manage, it’s much more than a kindness: if you avoid those conversations with them, it could end up affecting their performance, their evaluations, their raises, and their professional reputation. Most people want their managers to be up-front with them when those things are at stake.
Ultimately, though, when the potential for even mild conflict is causing this much worry, it’s almost certainly less about the specific conflict at hand and more about something a whole lot bigger. So really do think about therapy, as an investment not only in your career but in your quality of life too.
Update:
I realized, after reading your reply and the comments, that I was letting my self worth get too caught up in feeling like I wasn’t standing up for myself, and then beating myself up for it, which made the stakes feel even higher next time, which made it feel even harder to stand up for myself because it felt symbolic, instead of just a simple but tough work interaction. I decided to strip all that away and identify and attack the problem as systematically as possible.
The problem: People were saying inappropriate and sexist things to me, and I kept getting too anxious to tell them to knock it off.
The solution:
1) Reframe who had the power in these situations. I don’t need to network with these people, I don’t need these people to recommend me for other jobs because I do not want to work with them again. In a way, by being so upfront about their sexism they were giving me the gift of letting me know immediately not to waste my time, and the people who would be missing out on work is them, because I would never recommend them for jobs in the future and would actively discourage hiring them if I was able. Any short term jobs I miss out on now, are well worth it to form a network of people that are actually respectful that I want to keep working with.
2) Give up on ever having that perfect retort that would wither them to their bones, or beautiful speech that would change their life. Instead, I wrote out some very simple, one line, adjustable scripts for every situation I’d come across.
3) Embrace the power of awkward silence. Since I don’t have it in me to make a scene instead just say my one line script, and not say anything else or make it better. Let it be uncomfortable without anyone ever being able to say I was being unprofessional.
4) Practice in lower stakes situations. I did it at a bar, it worked like gangbusters.
5) Go through all my clothes, and pick out all the ones that make me feel as confident as possible, and project the image I want. Only wear those clothes to work, even though it’s just the same ones over and over again.
6) Wait for someone to do something and see how I do.
Results:
Yesterday, an older gentleman went on a long, highly inappropriate ramble and halfway through I interrupted and said, “You don’t need to tell me this, it’s making me uncomfortable.” He was very shocked and offended and just talked and talked and talked about why he wasn’t doing anything wrong, and I said nothing, and I kept saying nothing just staring at him as expressionlessly as possible, until he ran out of reasons why nothing he had done was wrong, and then he actually apologized! I told him I appreciated his apology, and then I left. No one told me not to show up tomorrow, and later on, other people came up to me to talk about it and seemed impressed with how I handled the situation. And actually addressing it in the moment, meant I didn’t have an anxiety about it, because it was all done and over. I felt great! I’m calling this a win.
I could write you a whole essay about how interesting it’s been starting this experiment in simple, practical ways to resist sexism, and then midway through have the whole industry basically implode over the Weinstein case, and everything else that’s come out after. At least for now, people are being more careful which is nice even if it is just out of fear. Hopefully it stays that way.
Also, I got a slight jump in title and pay, and being no longer replaceable in five minutes plus traffic has done wonders for making me feel less anxious at work.
Thank you for you and your commenters’ help!

no subject
no subject
yes 100%. Although also she hasn't quite realised that the awkward silence is (sometimes) the perfect retort, and I am so happy for her that it worked in this instance.
no subject