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‘How Can I Be More Assertive at Work?’

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Dear Boss,

Ever 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 said in a confident, non-panicky way without feeling like I’m going to die? 

I work in an entry-level job in 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 résumés, so being liked and keeping professional relationships alive is a really important skill set, 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 you’re going adrenaline-crazy 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 her 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 really 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 work call?” Those aren’t inflammatory requests, and they’re not going to sound like attacks or like crazily 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 that 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 co-worker 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.

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‘How Can I Be More Assertive at Work?’