Being an Introvert, and Asking For What You Want

As an introvert and Shy Person, my instinct in almost every social situation is to run—no followup questions, no small talk—just get out of there as soon as possible. And if I can avoid having an awkward conversation altogether? Even better.

But when it comes to money and managing my career, this instinct is pretty much all bad.

Being able to be open and assertive with people who have the power to impact your career is a really important skill, and one that usually takes regular practice to keep up. Your future success depends on being able to get what you want from those people in your life, even when the idea of broaching a tough conversation leaves your palms sweaty and your boots shaky.

I spent years cringing and nodding through work conversations, too timid to speak up when I thought something was wrong or when I needed something to do my job, and getting passed over for opportunities because of it.

Eventually, though, as is probably the case for lots of introverts, the fear of speaking up was outweighed by the fear of missing out on the things I wanted.

And you know what started happening when I started speaking up? I started getting what I wanted. Even if it was just clarification on why I was assigned one project and not another project. More often, what I got back was people agreeing with me: Yes, we can pay you that. Sure, you can take that on. All I had to do was ask.

It’s really hard for lots of people—introverts and extroverts—to get what they want at work. So start with some simple rules and soon enough, you’ll be taking charge of your career and making your goals and needs a priority.


Get to know them before you need something from them. Some bosses and clients are naturally super distant, and some are this way on purpose. But if someone who has the potential to impact your career isn’t reaching out to you, you had better figure out a way to reach out to them.

Why? Because when it comes time to ask them for more money or a promotion or a recommendation letter, you want them to already know who you are and why you deserve it. Think about it: If you have two people asking you for $50, but one is a friend and one is a stranger, who are you more likely to give the money to?

It’s your friend, obviously; and for lots of reasons, not the least of which are that you know, like, and trust her. Your boss feels the same way about handling salaries and promotions. Yes, doing exemplary work is important, but no, it’s not the only factor in decision-making. They’re only human.


Stay calm, and keep it simple. It can be tempting to preface requests for more money with a million apologies and “I know you’re busy”s or “I hope this doesn’t seem too out of line”s because you’re nervous and don’t want to seem greedy or like a troublemaker. But the more you lead into a conversation about money with phrases that don’t say anything, the more unprofessional you look and the more your boss sees the minutes on their clock ticking away.

Do a little research beforehand, so you know already that you’re not completely out of line. Have other people received raises or promotions after being with the company the same amount of time you have? Do you have recent examples of awesome work that demonstrate your value? If yes, then don’t worry. Just look them in the eye, be friendly, and make the ask—in three concise, but convincing sentences or less.


When people ask, speak up. As a freelance writer, I’ve been really lucky to have a few clients be incredibly helpful and supportive of my career. They’ve asked me questions like what I’d like to end up doing and who I’d like to meet, then they’ve taken steps to help me to make progress towards those goals.

Every time they ask, though, my first instinct is to shy away. I don’t want to tell them, because I feel embarrassed and I don’t want to be a burden. This is an instinct introverts have to fight at every turn in these situations, because when people want to help, you should let them. If they ask what you need, tell them. Not only because they can help you find opportunities, but it also makes them feel good and shows them you trust them.

Even if you think your boss should just know what you want by now, go ahead and lay it out for them just in case.


Ask clarification questions. I hate confrontation, and asking follow-up questions—especially if the subject is something I consider awkward, like money or recognition for work—can feel like I’m being rude or putting the other person in an uncomfortable position.

But if you don’t understand something, ask. It’s better to ask and have them explain something twice, than to go back to your desk having no idea what just happened. Plus, asking questions is a great way to give yourself a chance to process information.


Remember that it’s not weird. Managers know that part of their job is dealing with employee issues like salary, recognition, promotions, conflicts, and a slew of other things. As long as you make an appointment and maintain a rational tone, more often than not, your boss will be happy (or at least willing) to sit down with you and discuss whatever you need.

When I decided to stand up for myself at work, it wasn’t easy and it didn’t come naturally. But little by little, I decided that no matter how awkwardly they came out, I would ask questions. No matter how dry my mouth got, I would speak up in meetings. No matter how pale and sweaty I became, I would hold my ground in one-on-ones until my boss and I were on the same page.

What’s that one thing you need? Why not start asking for it?


Previously: Meet People, Get a Job (Even If You’re an Introvert)

Kate Stull is a writer living in Seattle who’s trying to be more assertive. She’s finally getting the hang of Twitter, and just helped create a website.



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